Distinctive Properties in Chicago’s Most Vibrant Neighborhoods

Staywell Hospitality is a curated collection of exceptional apartments in Chicago’s most vibrant neighborhoods. Book direct with us and save.

Chicago

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Spectacular Fulton Market Penthouse, Sleeps 24 in Style | Featured In Architectural Digest

4.85 (110)

Chicago, Illinois

6 bedrooms•4 baths

$1,628for 3 nights•Jan 4 – Jan 7

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

4.78 (236)

Chicago, Illinois

2 bedrooms•2 baths

$583for 3 nights•Jan 4 – Jan 7

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Experience Chicago Like You Live Here

Staywell Hospitality offers a curated collection of thoughtfully appointed apartments in Chicago’s most vibrant neighborhoods. Designed for family, business and leisure travelers alike, our residences combine the space and comfort of a private home with the quality, consistency, and care of professional hospitality. Whether visiting for a weekend or an extended stay, enjoy the freedom to settle in, explore the neighborhood, and experience Chicago on your own terms.

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What Guests Say

Trusted by Travelers

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!