Amazing hotels in Chicago
A carefully curated list of hotels and vacation rentals in Chicago. We've spent days researching the best hotel recommendations for you.
The Publishing House
The best place I’ve stayed in Chicago. Location was great. Out of the hustle and bustle but just barely. Easy access to downtown!
The warmth and hospitality of a classic B&B in the dress of a hip boutique hotel. Based in the trendy neighbourhood “the West Loop” this bed and breakfast will blow your mind.
Show full descriptionLocated in a century-old building that used to be a publishing house, The Publishing House is an independent B&B run by husband and wife. The 11 rooms are individually designed and, keeping the publishing theme, named after famous writers. The property shines with the industrial charm of the building (exposed brick, high ceilings, large windows) that is mixed with tasteful flea-market furniture, kilim rugs and bold original artwork.
Cool specials:
- amazing home-cooked breakfast (mentioned by so many guests!)
- free fresh pastries in the guest-kitchenette
- in-house library (books can be purchased)
- wine bar in the cellar, serving good wines & snacks
- hosts are available by text or phone
Good to know:
- Two pugs live on-site
- Room sizes are differing a lot
Chicago Athletic Association
To say that the customer service was 5 stars would be an understatement. Please do check out the Game Room and have breakfast in the Drawing Room.
A unique hotel in a unique building: The Athletic Association building used to house an elite men’s club. The historical heritage has been sustained but modern amenities make this place a comfortable and exclusive place to stay.
Show full descriptionAbout the hotel:
- Located downtown
- Rooftop bar overlooking Millennium Park
- Seven unique restaurants & bars on-site
- Beautiful,restored 19th-century interior (brass fixtures, carved stone fireplaces, terrazzo floors)
- Fitness center on the 9th floor
- 240 rooms with varying size, all individually designed
- Indoor golf simulator
Good to know:
- Minibar stocked with local brands
- Not-so-classic sweatshirt-fabric robes modeled on boxers’ cover-ups
- Front desk staff have tour-guide-level knowledge about the architecture and art of the building
- Top floors offer sweeping views to Lake Michigan
- Only steps away from the Art Institute of Chicago or the Chicago Symphony Orchestra
Urban Glamping at The Gwen
The rooms, food and hospitality at the Gwen is second to none.
Exclusively in the months from May through September, The Gwen offers a unique glamping experience on the 16th-floor private terrace. Guests get picturesque views of the city’s most iconic architecture and can spend the night under the stars. Also, the rest of the hotel is worth a visit.
Show full descriptionGlamping at The Gwen:
- A glamourous 16-fee diameter glamping tent
- On a private 1,000 square feet terrace on the 16th floor of the building
- Elegant, bohemian decor
- Access to the Gwen Lux Suite, a two-bedroom suite featuring a dining room, living room, and two-and-a-half baths
- Welcome bite
- Round-trip airport transportation
- The tent and suite combination accommodates up to six guests
- VIP guest status, providing access to the hotel’s Elite Ambassador Service
The hotel:
- Very centrally located
- Situated in the Art Deco landmark, the McGraw-Hill building
- Modern rooms, decor in line with the Art Deco theme of the building
- Connected via an indoor bridge to The Shops at North Bridge
- No spa, only a small fitness facility
- Free coffee available in the lobby
- Suites and king-sized rooms have deep soaking tubs
Food:
- Three restaurants/bars on-site
- Lounge with a rooftop terrace that opens with warm weather
The Robey
The corner suites also are excellent offering great views of downtown Chicago and the surrounding area.
The iconic North Tower of the Art Deco skyscraper in Wicker Park is home to The Robey. It also hosts a rooftop swimming pool, a rare find in Chicago.
Show full descriptionThe hotel:
- 89 guest rooms
- A somewhat experimental but sophisticated design style
- Modern, industrial style with a vintage twist (hardwood floors, chrome, frosted glass)
- The rooms feature custom-designed furniture
- Restaurant, lobby, and rooftop lounge on site
Amenities:
- Café Robey, a neighborhood restaurant with a French-American cuisine for breakfast, lunch, and dinner
- Guest-only lobby
- Rooftop cocktail bar on the 13th floor, for drinks and stunning views of the city skyline
- Open for public indoor/outdoor cocktail bar and rooftop pool, with 180-degree views
- Complimentary bikes
Good to know:
- The triangular-shaped Corner Suites have the best views
- Also, the Panorama Suite gives 180-degree views
Special:
- Rooftop terrace and pool
- Custom-made denim bathrobes
Longman and Eagle Inn
They even leave you two tokens for a free whiskey or coffee in their restaurant when you stay.
This 6-room-only inn is nested above the popular restaurant Longman & Eagle. If you’re looking for accommodation off the beaten path, this is your place to stay.
Show full descriptionDetails:
- Only 6 guest rooms
- Differing in size
- No breakfast, but the neighborhood is filled with excellent restaurants and cafés
- Located in the Logan Square neighborhood
- Funky, individually designed rooms with a casual style but eye-catching details
Special:
- Some of the rooms come with vintage tape decks and homemade mixed tapes
- A great selection of books by local authors or about local subjects to peruse
- Guests receive wooden chips to trade in for drinks at the downstairs bar
Good to know:
- It can get a bit noisier here than in a generic hotel, the bedrooms are above a bar
- If you want to try the downstairs restaurant be sure to make a reservation, it’s popular
21c Museum Hotel Chicago
We weren’t expecting a full blown art museum within this boutique hotel.
Did you ever dream about spending the night in a museum? In the 21c Museum Hotel, this dream becomes true. A unique hotel with contemporary art around every corner.
Show full descriptionThe hotel:
- Located in the Michigan Avenue Shopping district
- Based in free contemporary art, multi-venue museum
- 297 rooms
- spacious guest rooms
- Bright and airy design, with muted colors and an elegant style. Quite a contrast to the bold and colorful art installations guests can find all over the public space
- 24-hour fitness center available
- Concierge services available
- Breakfast and lunch restaurant available on-site; it becomes a seafood restaurant by night
The Guesthouse
We loved having a reserved parking space in the garage, which was even equipped with an EV charger.
A little outside of the center of Chicago The Guesthouse offers 25 spacious and completely self-contained suites for guests who want to get a more local experience of Chicago.
Show full descriptionThe rooms:
- Cozy and warm feel thanks to old barn wood, natural colors, leather, and open fireplaces
- One-, Two- and Three-Bedroom Suites available, perfect for families
- All suites come with fully equipped gourmet kitchens
- Washer and tumble dryers also included
- Units include a living area, separate bedrooms, private bathrooms, and balconies with a barbeque grill
Amenities:
- On-site fitness center
- 24-hour front desk
- Mini-market
- Lounge
- Rooftop deck
- Library
- A small boutique with local products and items from small businesses
Good to know:
- Not ideal for standard tourist attractions, the center can be reached within about 40 minutes
- No restaurant on site but agreements with popular local restaurants: In the morning guests can get breakfast delivered, in the evening Italian dishes or pizza
Sophy Hyde Park
It’s right on lively 53rd St, but our room on the 4th floor was very quiet.
A classic and tasteful boutique hotel that’s located in the neighborhood of Hyde Park. This area is home to many cultural establishments, such as the picturesque University of Chicago campus or the Museum of Science and Industry. Matching its location the artistic hotel was inspired by the legacy of the fine arts of Hyde Park.
Show full descriptionThe rooms:
- 98 guest rooms
- Elegant luxury with abstract art elements
- Room interior includes hardwood flooring, marble-tiled bathrooms with walk-in showers, custom lighting, and comfortable seating area
- Every room comes with an eight-foot abstract painting by local artist Joey Korom and a record player and a vinyl selection of local musicians
The amenities:
- On-site restaurant with 7-days a week brunch instead of breakfast and lunch service
- Library with contemporary literature
- 24/7 fitness center
- Room service
The hotel:
- Hotel lobby with a cozy double-sided fireplace
- Lots of cummunity-inspired artwork
- A small outdoor lounge area
- Private dining room available for up to 14 people
What’s special?
The restaurant artwork includes pieces designed specifically for the hotel by students at nearby Hyde Park Academy High Schoolnear South Side Chicago
Villa D’ Citta
We did lots of sightseeing all within easy access either by public transport, which is nearby, or by walking.
Villa D’ Citta is a rare find, nestled in the heart of the city’s trendy Lincoln Park neighborhood. The romantic bed-and-breakfast invites guests on a trip to Europe: The place comes in an authentic Italian style and is featuring large, luxurious rooms.
Show full descriptionHotel:
- A 19th-century stone mansion with Italian architecture
- A beautiful Grotto-style courtyard with BBQ
- Sundeck with outdoor whirlpool
- Spacious rooms with fireplaces
- Bicycles available for rent on site
Food:
- Daily continental breakfast and hot breakfast on weekends
- Free coffee, juice, and ingredients in the communal kitchen
- No restaurant on site
Things to do:
- Only steps away from Chicago’s number one boutique shopping district
- Close to restaurants, bars, and beaches
- Two blocks from three subway lines
Good to know:
- Far from the city’s top tourist attractions
- Two rooms have a shared bathroom
- Parking can be a challenge
