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Staywell Hospitality

Partner With Staywell Hospitality

We handle everything, from guest screening to monthly payouts, so you don't have to.

Chicago Specialists, Not a National Platform

Every home in our portfolio sits in Chicago's most sought-after neighborhoods: the Loop, Fulton Market, Streeterville, and River North. We know these buildings, these guests, and this market. Several of our homes have been featured in Architectural Digest, and we manage properties that sleep anywhere from four to twenty-four guests. When you list with us, you get a team that already knows what works here.

What We Do

Full-Service Property Management

Industrial loft living room with exposed brick walls, large windows, wooden ceiling beams, and mixed seating including gray sofa and leather chairs

Guest Screening & Booking

We handle reservations, guest communication, and vetting so you don't.

  • Careful guest selection

  • Direct owner support

  • Transparent booking flow

Modern living room with teal sofa, wooden desk, and large windows overlooking historic city buildings

Revenue & Reporting

Clear numbers, fair pricing, and straightforward payouts every month.

  • Market-rate pricing

  • Detailed statements

  • Reliable payments

Modern high-rise apartment living room with city skyline views, mid-century furniture, and floor-to-ceiling windows

Maintenance & Turnover

Your home stays in top shape between every guest arrival.

  • Regular inspections

  • Quick-response repairs

  • Professional cleaning

Proven Track Record

Performance Owners Rely On

4.80

4109 reviews

The location is spectacular - very walkable! When I entered the unit, I immediately noticed how clean it smelled and looked. The beds and furniture are so comfortable. It's very spacious! The check in process was very easy and the staff at the reception desk was so kind and helpful. It's a beautiful building with great amenities - check out the 18th floor wrap around balcony with seating and the most amazing view. I will definitely stay here again and would happily choose another Staywell property. All in all a wonderful experience!

Sara

Stayed in November 2026

The place was great. Had an amazing stay in Chicago! I’ll definitely will be back!

Shanita

Stayed in November 2026

We had a wonderful stay! The location was amazing and within walking distance of just about everything. The beds were comfortable, and the space was so cute and thoughtfully decorated. You could hear the train at night, but the white noise machine worked wonders, so it wasn’t an issue for us. We felt safe, comfortable, and welcomed throughout our stay. We would absolutely stay here again and highly recommend it!

Erica

Stayed in November 2026

10/10 would stay again, and the host was also great! I loved every minute of my stay here!

Jorge

Stayed in November 2026

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