Spectacular 2BR Penthouse in the Loop | Roof Deck Chicago, Illinois · 2 bedrooms Rated 4.81 (371 reviews)- Where
- Chicago
- Homes
- Apartments and condos, typically 2 bedrooms
- Hosting
- Own Airbnb account
Markets
Where Does Staywell Operate?
Staywell runs listings in Chicago.
Every market, with its rank there
Active Airbnb homes run as host or co-host in each market, 12 months to October 2026. Rank there is the company's place on that market's page. Market data links go to the market's own report, apart from any ranking.
| # | Market | Homes |
|---|---|---|
| Chicago Illinois | 25 |
A rank is shown where the market has its own ranking page. Ahead of similar homes: the first measure its year-round homes there are ahead of owner-run homes of the same size and type on (revenue, then nightly rate, then booked nights), on 10 or more homes; a count alone is how many homes were compared. The market's page shows the same cell. † A lead of 150% or more also reflects the homes themselves: their size, finish and location count alongside the management.
Results
Where Do Staywell's Homes Out-Earn Similar Ones?
Staywell's year-round homes earn more Airbnb revenue than similar owner-run homes in Chicago. Each comparison is with owner-run homes of the same bedrooms and room type in the same city.
Homes
What Kind of Homes Does Staywell Run?
Staywell lists only apartments and condos, in markets where apartments and condos are 75% of the listings. Its typical home has 2 bedrooms.
2 bedrooms is Staywell's most common size, at 52% of its homes
Share of active listings by bedrooms, 12 months to October 2026
- Staywell's listings
- Across its markets
Apartments and condos: 100% of Staywell's homes, against 75% in its markets
Share of active listings by property type, 12 months to October 2026
Staywell
- Apartment & Condo 100%
Its markets
- House 19%
- Apartment & Condo 75%
- Boutique & Hotels 4%
- Others 2%
Some of its best-reviewed homes
- Spectacular 2BR Penthouse in the Loop | Roof Deck Chicago, Illinois · 2 bedrooms Rated 4.81 (371 reviews)
Chic Penthouse Corner 3BR Loft In Fulton Market | Chicago, Illinois · 3 bedrooms Rated 4.85 (294 reviews)
Beautiful Luxury Loft in Fulton Market, Sleeps 12 Chicago, Illinois · 2 bedrooms Rated 4.85 (286 reviews)
Stunning Corner 2BR in the Loop | City & Lake View Chicago, Illinois · 2 bedrooms Rated 4.85 (234 reviews)
Designer 3BR Penthouse in Heart of Fulton Market Chicago, Illinois · 3 bedrooms Rated 4.80 (220 reviews)
Spectacular Corner 3BR in the Loop | City Views Chicago, Illinois · 3 bedrooms Rated 4.80 (212 reviews)
Rated 4.8 or higher by guests over 20 or more reviews.
Size
How Big Is Staywell?
| Rank | Ranking | Listings |
|---|---|---|
| 35 | 35th largest in Illinois | 25 |
| 25 | 25th largest in Chicago | 25 |
Companies of Similar Size in Illinois
- Ren #31 · 27 listings
- Hosty #32 · 27 listings
- House Of Living #33 · 26 listings
- Suhasini #36 · 23 listings
- Escape Stays #37 · 22 listings
- Zylene Mae #38 · 22 listings
- See the full ranking in Illinois
Checks
Is Staywell Legit?
In AirROI's data, Staywell is an active Airbnb business: 25 active listings and 5,245 guest reviews, run from one public Airbnb host account. AirROI checks activity on Airbnb's public listings. It doesn't certify companies or judge how they treat owners, so ask for references and read the contract.
- Airbnb account
- Staywell (25 homes). Accounts updated October 2026.
- Listings and reviews
- 25 active listings, 5,245 guest reviews
- Markets
- 1 market in Chicago
- How it hosts
- On its own Airbnb accounts
Questions
Questions About Staywell
What does Staywell charge?
AirROI does not publish or estimate any single company's fee, so ask Staywell for its rate card in writing, and what it covers.
Where does this data come from?
AirROI counts the active Airbnb homes run from Staywell's public host account, as host or co-host, over the 12 months to October 2026, each home once. The counts cover Airbnb only, so its full portfolio may be larger.
About the data
About This Data
Every figure comes from AirROI's data on active Airbnb listings over the 12 months to October 2026: listings open to bookings through the year, run by the company as host or as co-host on the owner's account. The company's Airbnb accounts with 5 or more listings are joined by name, so smaller accounts may be missing and the counts are a floor; homes listed only on other sites are not counted. Nothing is self-reported. Profiles are refreshed every month, next in December 2026. The method page gives how homes are counted, how accounts are credited and joined, and how a region is drawn.