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Airbnb City Guide: The Best Places To Invest in Chicago, Illinois

Gray High-rise Buildings in Chicago

Airbnb Rules and Regulations in Chicago, Illinois

Chicago has comprehensive rules and regulations for short-term rentals. Hosts must obtain a vacation rental license from the city and comply with zoning restrictions, which limit rentals to specific areas. Also, hosts must register with the city, pay a 4% rental tax, and maintain liability insurance.

Rentals are limited to a maximum of 90 days per year for single-family homes and 180 days for multi-unit buildings. Hosts must also provide guests with a summary of the city's noise, trash, and parking ordinances. Failure to comply with these regulations can result in fines and the revocation of the rental license.

Despite these restrictions, Chicago remains a popular destination for Airbnb guests, offering a diverse range of neighborhoods and attractions. By staying informed and adhering to the city's rules, hosts can successfully navigate the short-term rental market and provide memorable experiences for their guests.

Chicago Airbnb Market Data:

  • Occupancy Rate – 60%
  • Average Revenue – $49.3K per year
  • Average Daily Rate – $224.6 per night
  • Average RevPAR – $135.5
  • Average Home Prices – $284,818

1. Top Place to Invest in Chicago, Illinois - River West

River West, a vibrant and rapidly growing neighborhood just west of the Chicago River, has emerged as a top destination for real estate investment. With its convenient location, unique blend of industrial charm and modern amenities, and thriving arts and food scene, River West offers an attractive opportunity for veteran or new Airbnb investors.

River West Airbnb Market Data:

  • Occupancy Rate – 71%
  • Average Revenue – $103.9K per year
  • Average Daily Rate – $401.8 per night
  • Average RevPAR – $282.4

Convenience (Score: 9/10)

River West boasts excellent accessibility, with two CTA Blue Line stations providing quick and easy access to downtown Chicago and O'Hare International Airport. The neighborhood is also well-connected by bus lines and major thoroughfares, including the Kennedy Expressway (I-90) and Ogden Avenue. The area's walkability and bike-friendly streets make it easy for visitors to explore local shops, restaurants, and attractions.

Tourist Attractions (Score: 7/10)

While River West may not be a traditional tourist hotspot, it offers several unique attractions that showcase the neighborhood's rich history and vibrant culture. The Chicago Architecture Center's walking tours highlight the area's industrial past and modern transformation. The nearby Chicago Riverwalk provides a scenic spot for visitors to stroll, dine, and enjoy waterfront views. The neighborhood's thriving arts scene, with galleries like the Weinberg/Newton Gallery and the Mars Gallery, attracts art enthusiasts from across the city.

Things to Do (Score: 8/10)

River West offers a diverse array of activities and entertainment options. The neighborhood's eclectic mix of restaurants and bars, such as The Dawson, Piccolo Sogno, and Richard's Bar, cater to a variety of tastes and preferences. Music venues like The Mid and Bottom Lounge host live performances by local and national acts. Visitors can also explore the neighborhood's unique shops and boutiques, such as the Dial Bookshop and the Seek Vintage clothing store.

Average Home Prices (Score: 7/10)

According to Zillow, the typical home value in River West as of February 2024 is $475,000, representing a 4.5% increase over the past year. While this may seem high compared to some other Chicago neighborhoods, it is relatively affordable for a centrally-located, rapidly developing area. River West offers a mix of loft-style condos, townhomes, and new-construction apartments, catering to a range of budgets and preferences.

Proximity to Work-Related Travel (Score: 8/10)

River West's central location makes it an ideal base for work-related travel. The nearby Kennedy Expressway and CTA Blue Line provide quick access to downtown Chicago, the Illinois Medical District, and the University of Illinois at Chicago. The neighborhood is also close to major convention centers like UIC Forum and the Vertiport Chicago heliport. While there are no major sports venues within River West itself, the United Center, home of the Chicago Bulls and Blackhawks is just a short drive or public transit ride away.

X-Factor (Score: 9/10)

WhatItsque blend of industrial character, modern amenities, and community spirit. Th sets River West aparte neighborhood's former factories and warehouses have been transformed into trendy lofts, galleries, and event spaces, creating a distinctive aesthetic that appeals to both residents and visitors. River West's diverse population, which includes artists, professionals, and families, fosters a welcoming and inclusive atmosphere. The neighborhood's proximity to the Chicago River and its rapidly developing Riverwalk adds to its charm and potential for future growth.

2. Top Place to Invest in Chicago, Illinois - Chatham

Chatham, a historic and culturally rich neighborhood on Chicago's South Side, has emerged as an attractive investment opportunity for Airbnb and short-term rental (STR) investors. With its strong sense of community, affordable housing prices, and convenient location, Chatham offers a unique and promising destination for visitors seeking an authentic Chicago experience.

Chatham Airbnb Market Data:

  • Occupancy Rate – 46%
  • Average Revenue – $23.5K per year
  • Average Daily Rate – $139.1 per night
  • Average RevPAR – $64.4

Convenience (Score: 7/10)

Chatham's location provides relatively easy access to major highways, including the Dan Ryan Expressway (I-90/94) and the Chicago Skyway (I-90). The neighborhood is served by several CTA bus lines and the Metra Electric District line, connecting it to downtown Chicago and other parts of the city. However, public transportation options are somewhat limited compared to other Chicago neighborhoods. The area's walkability and bike-friendliness are improving, with ongoing efforts to enhance pedestrian safety and create more green spaces.

Tourist Attractions (Score: 6/10)

Chatham may not have many traditional tourist attractions as a primarily residential neighborhood. However, the area's rich history and cultural heritage offer unique opportunities for visitors to explore. The historic Chatham Fields, a former airfield that played a significant role in the development of aviation in Chicago, is a notable landmark. The nearby Tuley Park features a fieldhouse, playground, and outdoor basketball courts, providing a glimpse into the community's recreational activities.

Things to Do (Score: 7/10)

Chatham offers a variety of community-oriented activities and events that provide a glimpse into the neighborhood's vibrant culture. The Chatham Education and Workforce Center hosts a range of programs, including job training, entrepreneurship workshops, and youth development initiatives. The annual Chatham Summerfest brings together residents and visitors for a day of live music, food, and family-friendly activities. Visitors can also explore the area's emerging food scene, with local favorites like Brown Sugar Bakery and Uncle Joe's Jerk Chicken.

Average Home Prices (Score: 9/10)

According to Zillow, the typical home value in Chatham as of February 2024 is $175,000, representing a 6.1% increase over the past year. This is significantly more affordable compared to other Chicago neighborhoods, making Chatham an attractive option for investors looking to enter the STR market. The area offers a mix of single-family homes, condos, and multi-family properties at various price points, providing opportunities for different investment strategies.

Proximity to Work-Related Travel (Score: 7/10)

Chatham's location provides relatively convenient access to major employment centers, including downtown Chicago and the Illinois Medical District. The nearby I-90/94 and I-90 expressways connect the neighborhood to other parts of the city, although traffic congestion can be a challenge during peak hours. The area is also close to several hospitals, such as the Advocate Trinity Hospital and the St. Bernard Hospital.

X-Factor (Score: 8/10)

Its strong sense of community and rich cultural heritage sets Chatham apart. The neighborhood has a long history of African-American entrepreneurship and activism, with notable figures like Mahalia Jackson and Gwendolyn Brooks calling Chatham home. The area's tight-knit community and active neighborhood organizations work together to promote economic development, improve public safety, and celebrate Chatham's unique identity. This strong community spirit, the neighborhood's affordable housing prices, and its convenient location make Chatham a promising destination for STR investors looking to be part of an authentic Chicago experience.

3. Top Place to Invest in Chicago Illinois - Near North Side

The Near North Side, a vibrant and bustling neighborhood in the heart of Chicago, has emerged as a top destination for real estate investment. With its prime location, world-class attractions, and luxurious amenities, the Near North Side offers an unparalleled opportunity for Airbnb and short-term rental (STR) investors looking to capitalize on the city's thriving tourism industry.

Near North Side Airbnb Market Data:

  • Occupancy Rate – 64%
  • Average Revenue – $83.6K per year
  • Average Daily Rate – $359 per night
  • Average RevPAR – $214.8

Convenience (Score: 10/10)

The Near North Side boasts unbeatable accessibility, with numerous CTA bus and train lines, including the Red, Brown, and Purple Lines, providing quick and easy access to the rest of the city. The neighborhood's central location and walkable streets make it a breeze for visitors to explore nearby attractions, restaurants, and shopping destinations. The area is also well-connected to major highways, such as Lake Shore Drive and the Kennedy Expressway, making it easy for guests to arrive by car.

Tourist Attractions (Score: 9/10)

The Near North Side is home to some of Chicago's most iconic tourist attractions. The Magnificent Mile, a stretch of Michigan Avenue known for its high-end shopping and dining, draws millions of visitors each year. The neighborhood also boasts world-renowned museums like the Museum of Contemporary Art and the Richard H. Driehaus Museum. Other popular attractions include the John Hancock Center observation deck, the historic Water Tower, and the Navy Pier, which offers a variety of entertainment options and stunning lake views.

Things to Do (Score: 9/10)

In addition to its many tourist attractions, the Near North Side offers a wide range of activities and entertainment options. The neighborhood's diverse dining scene includes Michelin-starred restaurants, trendy cafes, and classic Chicago deep-dish pizza joints. Visitors can also enjoy live performances at venues like the Broadway Playhouse and the Lookingglass Theatre Company. The area's numerous parks and green spaces, such as Lake Shore Park and the Riverwalk, provide outdoor recreation and relaxation opportunities.

Average Home Prices (Score: 6/10)

According to Zillow, the typical home value in the Near North Side as of February 2024 is $550,000, representing a 3.8% increase over the past year. While this may seem high compared to other Chicago neighborhoods, it is relatively reasonable for a prime downtown location. The Near North Side offers a mix of luxury condos, great for Airbnb Luxe rentals, townhomes, and historic brownstones, catering to a range of budgets and preferences. However, investors should be prepared for higher property taxes and maintenance costs associated with owning real estate in this desirable area.

Proximity to Work-Related Travel (Score: 9/10)

The Near North Side's central location makes it an ideal base for work-related travel. The neighborhood is within walking distance of numerous corporate offices, including the Aon Center and the Tribune Tower. The nearby Streeterville neighborhood is home to several major hospitals, such as Northwestern Memorial Hospital and the Ann & Robert H. Lurie Children's Hospital. The McCormick Place Convention Center and the United Center, home of the Chicago Bulls and Blackhawks are also easily accessible via public transportation or a short drive.

X-Factor (Score: 9/10)

Its unbeatable combination of location, luxury, and lifestyle sets the Near North Side apart. The neighborhood's stunning architecture, which includes historic landmarks and modern high-rises, creates a unique and sophisticated atmosphere. The area's proximity to Lake Michigan and its numerous parks and green spaces offer a tranquil escape from the bustling city. The Near North Side's diverse population and vibrant cultural scene, with galleries, theaters, and festivals, add to its appeal for visitors seeking an authentic Chicago experience.

4. Top Place to Invest in Chicago, Illinois - Pilsen

Pilsen, a vibrant and culturally rich neighborhood on Chicago's Lower West Side, has emerged as a top destination for real estate investment. With its unique blend of Mexican-American heritage, thriving arts scene, and convenient location, Pilsen offers an attractive opportunity for Airbnb and short-term rental (STR) investors looking to capitalize on the growing demand for authentic, immersive experiences in the heart of the city.

Pilsen Airbnb Market Data:

  • Occupancy Rate – 62%
  • Average Revenue – $33.1K per year
  • Average Daily Rate – $146 per night
  • Average RevPAR – $90.7

Convenience (Score: 8/10)

Pilsen's location provides excellent accessibility, with the CTA Pink Line offering quick and easy access to downtown Chicago and other parts of the city. The neighborhood is also well-connected by bus lines and major thoroughfares, including the Stevenson Expressway (I-55) and Cermak Road. Pilsen's walkable streets and bike-friendly infrastructure make it easy for visitors to explore the area's numerous shops, restaurants, and attractions.

Tourist Attractions (Score: 8/10)

Pilsen is known for its vibrant street art scene, with colorful murals adorning buildings throughout the neighborhood. The National Museum of Mexican Art, the largest Latino cultural institution in the United States, showcases a wide range of Mexican art and cultural exhibits. The Pilsen Arts and Community House, a historic landmark, hosts various cultural events and performances throughout the year. The neighborhood's numerous art galleries, such as the Chicago Arts District and the Pilsen Outpost, attract art enthusiasts from across the city.

Things to Do (Score: 9/10)

Pilsen offers a diverse array of activities and entertainment options. The neighborhood's thriving food scene includes authentic Mexican restaurants, trendy cafes, and popular food trucks. Visitors can explore unique shops and boutiques along 18th Street, such as the Pilsen Community Books and the Shaman Gallery. The annual Pilsen Fest and the Mole de Mayo Festival celebrate the neighborhood's Mexican-American heritage with live music, food, and cultural activities. Pilsen's numerous parks and green spaces, such as Harrison Park and Dvorak Park, provide opportunities for outdoor recreation and community gatherings.

Average Home Prices (Score: 8/10)

According to Zillow, the typical home value in Pilsen as of February 2024 is $375,000, representing a 5.6% increase over the past year. While this may seem high compared to some other Chicago neighborhoods, it is relatively affordable for a centrally-located, rapidly developing area. Pilsen offers a mix of historic single-family homes, multi-unit buildings, and new-construction condos, catering to a range of budgets and preferences. As the neighborhood continues to gentrify, investors can expect strong potential for appreciation in the coming years.

Proximity to Work-Related Travel (Score: 7/10)

Pilsen's location provides relatively convenient access to major employment centers, including the Illinois Medical District and the University of Illinois at Chicago. The nearby I-55 expressway connects the neighborhood to downtown Chicago and other parts of the city, although traffic congestion can be a challenge during peak hours. The area is also close to several hospitals, such as Saint Anthony and Mount Sinai.

X-Factor (Score: 9/10)

Its strong sense of community and authentic Mexican-American culture sets Pilsen apart. The neighborhood's vibrant street art, colorful murals, and cultural institutions create a unique and immersive experience for visitors. Pilsen's tight-knit community and active neighborhood organizations work together to preserve the area's cultural heritage while embracing new development and investment. The neighborhood's thriving arts scene, diverse food options, and welcoming atmosphere make it an attractive destination for visitors seeking a genuine Chicago experience.

5. Top Place to Invest in Chicago, Illinois - Hyde Park

Hyde Park, a vibrant and culturally rich neighborhood on Chicago's South Side, has emerged as a top destination for real estate investment. With its unique blend of historic charm, world-class attractions, and convenient location, Hyde Park offers an attractive opportunity for Airbnb and short-term rental (STR) investors looking to capitalize on the growing demand for authentic, immersive experiences in the heart of the city.

Hyde Park Airbnb Market Data:

  • Occupancy Rate – 70%
  • Average Revenue – $38.3K per year
  • Average Daily Rate – $150.4 per night
  • Average RevPAR – $106.9

Convenience (Score: 8/10)

Hyde Park's location provides excellent accessibility, with several major highways nearby, including Lake Shore Drive and the Chicago Skyway. The neighborhood is well-served by public transportation, with numerous bus lines and the Metra Electric District line connecting Hyde Park to downtown Chicago and other parts of the city. The area's walkability and bike-friendly streets make it easy for visitors to explore local shops, restaurants, and attractions.

Tourist Attractions (Score: 8/10)

Hyde Park boasts a variety of unique attractions that showcase the neighborhood's rich history and cultural heritage. The Museum of Science and Industry, the largest science museum in the Western Hemisphere, is a major draw for visitors of all ages. Other notable attractions include the DuSable Museum of African American History, the Oriental Institute, and the Frederick C. Robie House, a Frank Lloyd Wright-designed masterpiece. The nearby Jackson Park and Promontory Point offer stunning views of the Chicago skyline and Lake Michigan.

Things to Do (Score: 8/10)

Hyde Park offers a wide range of activities and events that cater to diverse interests. The neighborhood's thriving food scene includes a mix of ethnic restaurants, trendy cafes, and local favorites like Valois, the annual Hyde Park Jazz Festival, and the Silver Room Block Party, which attract visitors from across the city. The University of Chicago campus, with its gothic architecture and cultural offerings, is a must-see for architecture and art enthusiasts.

Average Home Prices (Score: 7/10)

According to Zillow, the typical home value in Hyde Park as of February 2024 is $270,000, representing a 57.9% increase over the past year. While this may seem high compared to some other Chicago neighborhoods, it is relatively affordable for a prime location with access to world-class amenities. Hyde Park offers a mix of historic homes, fully-furnished condos, and apartments at various price points, catering to different budgets and preferences.

Proximity to Work-Related Travel (Score: 8/10)

Hyde Park's location makes it convenient for work-related travel. The nearby University of Chicago Medical Center is a major employer and attracts healthcare professionals from around the region. The neighborhood's proximity to downtown Chicago and easy access to public transportation make it an ideal base for those attending conventions at McCormick Place or events at the United Center.

X-Factor (Score: 9/10)

Hyde Park's unique blend of history, culture, and community spirit sets it apart. The neighborhood's diverse population, which includes academics, artists, and long-time residents, creates a vibrant and welcoming atmosphere. Hyde Park's rich cultural heritage, from its role in the 1893 World's Columbian Exposition to its significance in the civil rights movement, adds to its appeal for visitors seeking an authentic Chicago experience. The neighborhood's stunning architecture, beautiful parks, and access to the lakefront make it a truly special place to live and visit.

6. Top Place to Invest in Chicago, Illinois - Dunning

Dunning, a quiet and family-friendly neighborhood on Chicago's Northwest Side, has emerged as an attractive investment opportunity for Airbnb and short-term rental (STR) investors. With its convenient location, affordable housing prices, and growing community development initiatives, Dunning offers a unique and promising destination for visitors seeking a peaceful and authentic Chicago experience.

Dunning Airbnb Market Data:

  • Occupancy Rate – 57%
  • Average Revenue – $30.4K per year
  • Average Daily Rate – $147 per night
  • Average RevPAR – $83.8

Convenience (Score: 7/10)

Dunning's location provides relatively easy access to major highways, including the Kennedy Expressway (I-90) and the Tri-State Tollway (I-294). The neighborhood is served by several CTA bus lines and the Metra Milwaukee District West line, connecting it to downtown Chicago and other parts of the city. However, public transportation options are somewhat limited compared to other Chicago neighborhoods. The area's walkability and bike-friendliness are improving, with ongoing efforts to enhance pedestrian safety and create more green spaces.

Tourist Attractions (Score: 6/10)

Dunning may not have many traditional tourist attractions as a primarily residential neighborhood. However, the area's unique history and community spirit offer opportunities for visitors to explore. The Dunning-Read Conservation Area, a 23-acre nature preserve, provides a peaceful escape from the city and a glimpse into the neighborhood's natural beauty. The historic Chicago-Read Mental Health Center campus, now partially redeveloped, offers a unique perspective on the area's past.

Things to Do (Score: 7/10)

Dunning offers a variety of community-oriented activities and events that provide a glimpse into the neighborhood's friendly atmosphere. The Dunning Branch Library hosts a range of programs, including book clubs, storytimes, and educational workshops. The annual Dunning Fall Fest brings together residents and visitors for a day of live music, food, and family-friendly activities. Visitors might skip your Airbnb's kitchen and opt to explore the area's growing food scene, with local favorites like Smakosz Restaurant and Taurus Flavors.

Average Home Prices (Score: 9/10)

According to Zillow, the typical home value in Dunning as of February 2024 is $325,000, representing a 4.8% increase over the past year. This is significantly more affordable compared to other Chicago neighborhoods, making Dunning an attractive option for investors looking to enter the STR market. The area offers a mix of single-family homes, condos, and multi-family properties at various price points, providing opportunities for different investment strategies.

Proximity to Work-Related Travel (Score: 7/10)

Dunning's location provides relatively convenient access to major employment centers, including O'Hare International Airport and the nearby industrial parks. The Kennedy Expressway (I-90) connects the neighborhood to downtown Chicago, although traffic congestion can be a challenge during peak hours. The area is also close to several hospitals, such as the Presence Resurrection Medical Center and the Shriners Hospitals for Children.

X-Factor (Score: 8/10)

What sets Dunning apart is its strong sense of community and small-town charm within the city limits. The neighborhood's friendly residents, active community organizations, and a growing number of local businesses create a welcoming atmosphere for visitors. Dunning's affordable housing prices and convenient location make it an attractive option for budget-conscious travelers seeking a quiet and authentic Chicago experience. As the neighborhood continues to develop and attract new investment, STR investors have the opportunity to be part of a growing and close-knit community.

7. Top Place to Invest in Chicago, Illinois - Albany Park

Albany Park, a diverse and vibrant neighborhood on Chicago's Northwest Side, has emerged as a top destination for real estate investment. With its unique blend of cultural richness, convenient location, and affordable housing prices, Albany Park offers an attractive opportunity for Airbnb and short-term rental (STR) investors looking to capitalize on the growing demand for authentic, immersive experiences in the heart of the city.

Albany Park Airbnb Market Data:

  • Occupancy Rate – 59%
  • Average Revenue – $35.1K per year
  • Average Daily Rate – $161.9 per night
  • Average RevPAR – $96.6

Convenience (Score: 8/10)

Albany Park's location provides excellent accessibility, with several major highways nearby, including the Kennedy Expressway (I-90) and the Edens Expressway (I-94). The neighborhood is well-served by public transportation, with the CTA Brown Line and numerous bus routes connecting Albany Park to downtown Chicago and other parts of the city. The area's walkable streets and bike-friendly infrastructure make it easy for visitors to explore local shops, restaurants, and attractions.

Tourist Attractions (Score: 7/10)

While Albany Park may not have many traditional tourist attractions, the neighborhood's rich cultural diversity and community events offer unique experiences for visitors. The Albany Park Theater Project, a youth theater company, showcases the area's talent and creativity through original productions. The Global Garden Refugee Training Farm, a community garden and urban farm, provides a glimpse into the neighborhood's commitment to sustainability and social justice. The nearby North Park Village Nature Center offers a peaceful escape from the city with its walking trails and educational programs.

Things to Do (Score: 8/10)

Albany Park offers a wide range of activities and events that celebrate the neighborhood's diverse cultures and community spirit. The annual Albany Park World Fest brings together residents and visitors for a day of live music, dance performances, and international cuisine. The neighborhood's thriving food scene includes a variety of ethnic restaurants, such as Persian, Middle Eastern, and Latin American eateries. Visitors can also explore unique shops and markets, such as the Lawrence Fish Market and the Chicago Produce Market, which offer fresh and affordable groceries.

Average Home Prices (Score: 9/10)

According to Zillow, the typical home value in Albany Park as of February 2024 is $350,000, representing a 4.5% increase over the past year. This is relatively affordable compared to other Chicago neighborhoods, making Albany Park an attractive option for investors looking to enter the STR market. The area offers a mix of single-family homes, condos, quadplexes, and other multi-unit buildings at various price points, catering to different budgets and preferences.

Proximity to Work-Related Travel (Score: 7/10)

Albany Park's location provides relatively convenient access to major employment centers, including downtown Chicago and the nearby Ravenswood Industrial Corridor. The Kennedy Expressway (I-90) and the CTA Brown Line make commuting to the city center easy, although traffic congestion can be a challenge during peak hours. The neighborhood is also close to several hospitals, such as the Swedish Hospital and the Kindred Hospital North.

X-Factor (Score: 9/10)

Albany Park's unparalleled cultural diversity and strong sense of community are what sets it apart. The neighborhood is home to a wide range of ethnic groups, including Latino, Middle Eastern, and Asian communities, creating a vibrant and welcoming atmosphere for visitors. Albany Park's active community organizations, such as the Albany Park Community Center and the North River Commission, work to promote social justice, economic development, and cultural celebration. The neighborhood's affordable housing prices, convenient location, and unique character make it an attractive destination for travelers seeking an authentic and immersive Chicago experience.

8. Top Place to Invest in Chicago, Illinois - River North

River North, a trendy and vibrant neighborhood in the heart of Chicago, has emerged as a top destination for real estate investment. With its prime location, world-class dining and entertainment, and luxurious amenities, River North offers an unparalleled opportunity for Airbnb and short-term rental (STR) investors looking to capitalize on the city's thriving tourism industry.

River North Airbnb Market Data:

  • Occupancy Rate – 64%
  • Average Revenue – $81.9K per year
  • Average Daily Rate – $348.9 per night
  • Average RevPAR – $207.3

Convenience (Score: 10/10)

River North boasts unbeatable accessibility, with numerous CTA bus and train lines, including the Red, Brown, and Purple Lines, providing quick and easy access to the rest of the city. The neighborhood's central location and walkable streets make it a breeze for visitors to explore nearby attractions, restaurants, and shopping destinations. The area is also well-connected to major highways, such as the Kennedy Expressway (I-90/94) and Lake Shore Drive, making it easy for guests to arrive by car.

Tourist Attractions (Score: 9/10)

River North is home to some of Chicago's most popular tourist attractions. The Magnificent Mile, a stretch of Michigan Avenue known for its high-end shopping and dining, is just a short walk away. The neighborhood also boasts world-renowned art galleries like the River North Gallery District and the Museum of Contemporary Art. Other notable attractions include the Chicago Riverwalk, the House of Blues, and the historic Merchandise Mart, which hosts various trade shows and events throughout the year.

Things to Do (Score: 9/10)

In addition to its many tourist attractions, River North offers a wide range of activities and entertainment options. The neighborhood's diverse dining scene includes Michelin-starred restaurants, trendy cocktail bars, and popular rooftop lounges. Visitors can also enjoy live music and comedy performances at venues like the Laugh Factory and the Redhead Piano Bar. The area's numerous art galleries and showrooms, such as the Habatat Galleries and the Andrew Bae Gallery, provide a feast for the eyes and a unique shopping experience.

Average Home Prices (Score: 6/10)

According to Zillow, the typical home value in River North as of February 2024 is $520,000, representing a 3.5% increase over the past year. While this may seem high compared to other Chicago neighborhoods, it is relatively reasonable for a prime downtown location. River North offers a mix of luxury condos, lofts, and high-rise apartments catering to a range of budgets and preferences. However, investors should be prepared for higher property taxes and cleaning costs associated with owning real estate in this desirable area.

Proximity to Work-Related Travel (Score: 9/10)

River North's central location makes it an ideal base for work-related travel. The neighborhood is within walking distance of numerous corporate offices, including the Merchandise Mart and the Boeing headquarters. The nearby Loop district is home to several major convention centers, such as McCormick Place and the Hyatt Regency Chicago. The United Center, home of the Chicago Bulls and Blackhawks is also easily accessible via public transportation or a short drive.

X-Factor (Score: 9/10)

Its perfect blend of sophistication, creativity, and energy sets River North apart. The neighborhood's stunning architecture, which includes historic warehouses converted into chic lofts and modern high-rises, creates a unique and stylish atmosphere. River North's thriving art scene, with its numerous galleries and public installations, adds to its appeal for visitors seeking a culturally rich experience. The area's proximity to the Chicago River and its bustling Riverwalk provides a picturesque setting for outdoor dining, entertainment, and recreation.

9. Top Place to Invest in Chicago, Illinois - Norwood Park

Norwood Park, a charming and family-friendly neighborhood on Chicago's Northwest Side, has emerged as an attractive investment opportunity for Airbnb and short-term rental (STR) investors. With its convenient location, affordable housing prices, and a strong sense of community, Norwood Park offers a unique and promising destination for visitors seeking a peaceful and authentic Chicago experience.

Norwood Park Airbnb Market Data:

  • Occupancy Rate – 71%
  • Average Revenue – $27.9K per year
  • Average Daily Rate – $107.1 per night
  • Average RevPAR – $76.8

Convenience (Score: 8/10)

Norwood Park's location provides easy access to major highways, including the Kennedy Expressway (I-90) and the Tri-State Tollway (I-294). The neighborhood is well-served by public transportation, with the Metra Union Pacific Northwest line and several CTA bus routes connecting Norwood Park to downtown Chicago and other parts of the city. The area's walkable streets and bike-friendly infrastructure make it easy for visitors to explore local parks, shops, and restaurants.

Tourist Attractions (Score: 6/10)

Norwood Park may not have many traditional tourist attractions as a primarily residential neighborhood. However, the area's unique history and architectural charm offer opportunities for visitors to explore. The Norwood Park Historical Society, housed in the historic Noble-Seymour-Crippen House, provides a glimpse into the neighborhood's past and hosts various community events throughout the year. The nearby Superdawg Drive-In, a Chicago institution since 1948, is a must-visit for hot dog enthusiasts and those seeking a classic American dining experience.

Things to Do (Score: 7/10)

Norwood Park offers a variety of community-oriented activities and events that provide a glimpse into the neighborhood's friendly atmosphere. The Norwood Park Chamber of Commerce hosts annual events, such as the Norwood Park Fall Fest and the Norwood Park Holiday Market, which bring together residents and visitors for a day of food, music, and family-friendly activities. The area's numerous parks, including Norwood Park and Oriole Park, offer opportunities for outdoor recreation, such as hiking, fishing, and golfing.

Average Home Prices (Score: 9/10)

According to Zillow, the typical home value in Norwood Park as of February 2024 is $450,000, representing a 4.2% increase over the past year. This is relatively affordable compared to other Chicago neighborhoods, making Norwood Park an attractive option for investors looking to enter the STR market. The area offers a mix of single-family homes, condos, and multi-family properties at various price points, providing opportunities for different investment strategies.

Proximity to Work-Related Travel (Score: 7/10)

Norwood Park's location provides relatively convenient access to major employment centers, including O'Hare International Airport and the nearby industrial parks. The Kennedy Expressway (I-90) and the Metra Union Pacific Northwest line make commuting to downtown Chicago manageable, although travel times can be longer compared to more central neighborhoods. The area is also close to several hospitals, such as the Presence Resurrection Medical Center and the Advocate Lutheran General Hospital.

X-Factor (Score: 8/10)

What sets Norwood Park apart is its strong sense of community and small-town charm within the city limits. The neighborhood's friendly residents, active community organizations, and well-maintained homes create a welcoming atmosphere for visitors. Norwood Park's affordable housing prices and convenient location make it an attractive option for budget-conscious travelers seeking a quiet and authentic Chicago experience. The area's architectural diversity, which includes historic bungalows and Victorian-style homes, adds to its unique character and appeal.

10. Top Place to Invest in Chicago, Illinois - Near West Side

The Near West Side, a vibrant and historically diverse neighborhood just west of Chicago's Loop, has emerged as a top destination for real estate investment. With its convenient location, world-class attractions, and unique blend of cultural influences, the Near West Side offers an attractive opportunity for Airbnb and short-term rental (STR) investors looking to capitalize on the growing demand for authentic, immersive experiences in the heart of the city.

Near West Side Airbnb Market Data:

  • Occupancy Rate – 61%
  • Average Revenue – 63K per year
  • Average Daily Rate – $282 per night
  • Average RevPAR – $171.9

Convenience (Score: 9/10)

The Near West Side boasts excellent accessibility, with numerous CTA bus and train lines, including the Blue, Green, and Pink Lines, providing quick and easy access to downtown Chicago and other parts of the city. The neighborhood's proximity to major highways, such as the Eisenhower Expressway (I-290) and the Kennedy Expressway (I-90/94), makes it easy for visitors to arrive by car. The area's walkable streets and bike-friendly infrastructure, including the popular Chicago Riverwalk, make it convenient for guests to explore local attractions, restaurants, and shops.

Tourist Attractions (Score: 8/10)

The Near West Side is home to several world-renowned attractions that draw visitors from around the globe. The United Center, home of the Chicago Bulls and Blackhawks is a major sports and entertainment venue hosting concerts, shows, and other events. The neighborhood also boasts the historic Hull-House Museum, which showcases the legacy of social reformer Jane Addams and the settlement house movement. Other notable attractions include the UIC Pavilion, the Chicago Fire Soccer Club's home stadium, and the Greektown and Little Italy neighborhoods, which offer a taste of the area's rich cultural heritage.

Things to Do (Score: 8/10)

The Near West Side offers a wide range of activities and experiences that cater to diverse interests. Foodies will delight in the neighborhood's thriving culinary scene, with authentic Greek and Italian restaurants, trendy cafes, and popular food halls like the Chicago French Market. Art enthusiasts can explore the neighborhood's many galleries and studios, such as the Pilsen Arts and Community House and the Chicago Arts District. The area also hosts various festivals and events throughout the year, including the Randolph Street Market Festival and the Greektown Taste of the Aegean.

Average Home Prices (Score: 7/10)

According to Zillow, the typical home value in the Near West Side as of February 2024 is $550,000, representing a 3.8% increase over the past year. While this may seem high compared to other Chicago neighborhoods, it is relatively reasonable for a prime downtown location with access to world-class amenities. The Near West Side offers a mix of historic lofts, modern condos, and townhomes at various price points, catering to different budgets and preferences.

Proximity to Work-Related Travel (Score: 9/10)

The Near West Side's central location makes it an ideal base for work-related travel. The neighborhood is home to the Illinois Medical District, one of the nation's largest urban medical districts, which includes several major hospitals and research facilities. The nearby UIC campus and the Chicago Loop are major employment centers that attract professionals from various industries. The area is also close to McCormick Place, the largest convention center in North America, and the United Center, which hosts numerous corporate events and conferences.

X-Factor (Score: 9/10)

Its unique blend of history, diversity, and innovation sets the Near West Side apart. The neighborhood's rich cultural heritage, shaped by waves of immigrants from around the world, is reflected in its architecture, cuisine, and community events. The area's transformation from an industrial hub to a thriving mixed-use district showcases its resilience and adaptability. The Near West Side's proximity to downtown Chicago, combined with its vibrant arts scene, cutting-edge medical facilities, and a strong sense of community, make it a truly special place to live and visit.

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