Chicago

As of May 2026, Chicago, Aurora, Naperville, Joliet have 7,991 active Airbnb and VRBO listings. This represents a 8% decrease from the previous year.

The average Airbnb or VRBO in Chicago generates $47K per year. High-performing properties earn $109K/year, while low-performing properties earn $18K/year. This significant revenue spread suggests that property-specific appeal dictates earnings more than general market conditions, as high earners capture a disproportionate share of total demand.

Average home prices in Chicago vary by property size: 1-bedroom properties cost approximately $182K, 2-bedroom homes average $276K, 3-bedroom properties are around $374K, and 4+ bedroom homes average $490K. These prices reflect median home values across the Chicago, Aurora, Naperville, Joliet area.

Airbnb and VRBO can be profitable in Chicago, with an average gross yield of 12% across all properties. High-performing properties achieve yields up to 27%, which is considered top for short-term rental investment. Such a wide yield gap highlights that top-tier assets successfully leverage current supply constraints to maximize returns.

The average occupancy rate for Airbnbs and VRBOs in Chicago is 41%. This occupancy level, combined with an average nightly rate of $277, results in a RevPAR (revenue per available room) of $91 per day.

2-bedroom properties demonstrate the strongest performance in Chicago, with an average gross yield of 16% and annual revenue of $47K. These properties balance purchase price ($276K), operating costs, and rental demand most effectively in the Chicago market.

Short-term rental regulations vary by jurisdiction in the Chicago area. Chicago: Strict. Registration required, primary residence only, max 365 days/year, no investor-owned units. Active enforcement with fines and platform data monitoring. Aurora: Moderate. Business license required, zoning restrictions apply. Moderate enforcement, some unlicensed operations exist. Naperville: Strict. Prohibited in most residential zones except B&Bs with special permits. Enforcement through complaint-driven code violations. Joliet: Lenient. Business license needed, basic zoning compliance. Light enforcement, many operate without licenses. Always verify current regulations with local authorities and obtain necessary permits before operating a short-term rental.

The Chicago Airbnb and VRBO market is currently showing balanced with strong demand conditions. Supply has declined 8% year-over-year, while RevPAR has increased 5%. This indicates healthy demand growth outpacing supply, suggesting that the current market contraction is tightening competition and bolstering revenue potential for remaining active listings.

Launch around July, 2-3 months before peak summer season (October peaks). This pre-peak timing lets you build reviews when competition is -36% lower than peak months. Avoid launching during peak season when established listings dominate, or slow months (December-January) when gaining traction is harder.

The most common amenities in Chicago listings include: Air Conditioning (97%), Kitchen (96%), Tv (93%), Washing Machine (82%), Heating (79%). Amenities that boost revenue the most include Air Conditioning, Gym, Washing Machine, with Air Conditioning properties earning approximately 72% more ($63K/year vs $36K/year).

Monthly estimated revenue per listing in Chicago over the last 12 months: May: $3K, June: $3K, July: $4K, August: $3K, September: $3K, October: $4K, November: $3K, December: $2K, January: $1K, February: $1K, March: $3K, April: $3K. These figures are based on RevPAR (revenue per available room) multiplied by the number of days in each month.

The overall average nightly rate in Chicago is $277, up 22% year-over-year. By property size: 1-bedroom properties average $158/night, 2-bedroom properties average $242/night, 3-bedroom properties average $316/night, 4+ bedroom properties average $578/night. Rates peak in July and are lowest in February.

Guests in Chicago book an average of 33 days in advance, down 16% from last year. By property size: 1-bedroom: 30 days, 2-bedroom: 33 days, 3-bedroom: 35 days, 4+ bedroom: 37 days. Larger properties tend to have longer booking windows as guests plan group trips further ahead.

Over the past year, the Chicago Airbnb and VRBO market has seen the following changes: supply declined 8%, revenue per listing increased 5%, occupancy fell 6%, average nightly rates increased 22%, and lead time decreased 16%. These shifts indicate a transition toward a high-rate, lower-volume environment where shorter booking windows drive pricing power.

In Chicago, Saturday sees the highest booking demand while Tuesday has the lowest. Nightly rates peak on Saturday and are lowest on Monday. Weekends show 46% higher occupancy than weekdays.