Hotel vacation rentals in Chicago

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Top-rated hotel rentals in Chicago

Guests agree: these hotel rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Hotel room in The Loop

4.86 out of 5 average rating, 121 reviews

2 Queen Bedroom in Downton

Experience upscale accommodations & amenities in the heart of Chicago when you stay at Cambria Hotel. Located conveniently close to some top attractions, is ideal for both business travel and vacations. Make the most of your stay with our top-notch services & on-site restaurant that offers classic American cuisine. Unwind & relax in our comfortable guest rooms with Chicago-inspired décor. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

Superhost

Private room in Irving Park

4.7 out of 5 average rating, 60 reviews

$N-PrivateRoom+Safe North Area+Free Street Parking

Relax by yourself or with a friend or partner by staying at this peaceful place. A modern and classic art decorated apartment. You can rent this one or even the whole apartment if available. There is an extra sofabed in the living room or extra twin bed available for you to use if your party is larger than 3 people and if you reserve both rooms. In this unit you share the living room, kitchen and bathroom when renting only one private bedroom.

Superhost

Hotel room in West Loop

5 out of 5 average rating, 15 reviews

Light-flooded rooms and city views

- This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries. - While we love the wellness studio, we’re all about what’s above – namely the rooftop pool and Stephanie Izard’s Peruvian-inspired restaurant. - Chic rooms reflect the building’s industrial past with paneled leather headboards, warehouse-style floor-to-ceiling windows and local artwork.

Superhost

Hotel room in Wicker Park

4.81 out of 5 average rating, 117 reviews

Hotel Quality Meets Local Living Deluxe Studio 4A

Quaint, cozy and 100% private, our overnight Guest Rooms offer honest to goodness pillow top mattresses with 500 thread count linens. Comfortable, simple and clean, additional features include: Private glass and marble showers, comfy chair, desk, custom woodworking and molding abound. Carpeted floors, oriental rug, natural light, modern and vintage décor/furnishings, high speed internet access, soft comforters and thirsty towels.

Superhost

Hotel room in Glenview

4.75 out of 5 average rating, 24 reviews

Sunset views from our private balcony

Find our hotel just five minutes from Chicago Executive Airport, 20 minutes from O'Hare International Airport and within walking distance of several Glenview restaurants. Visit local corporations like Allstate, CVS Health, GN Beltone, NIPSTA and Astellas from our Illinois hotel, which also offers access to Chicago-area attractions like Kohl Children’s Museum, Chicago Botanic Garden and Ravinia.

Superhost

Hotel room in The Loop

4.75 out of 5 average rating, 4 reviews

An easy walk to the Art Institute

- Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required). - Beautifully reno'd historic gem. Jaw-dropper of a marble staircase greets you in the (also marble!) lobby. - Classic rooms rock a smart setup & airy palette – plus you have access to snacks, coffee/tea and more in the Club Living Room.

Superhost

Hotel room in Near North Side

4.82 out of 5 average rating, 121 reviews

Gritty Chic River North -- ACME Hotel

If you've never been one for convention, ACME is the right choice for you. Located 2 1/2 blocks from the Magnificent Mile in the River North neighborhood. We want your experience at ACME to blow your mind, not your budget, book a room, and be prepared to fall in love. Voted number 2 on Conde Nast Top Chicago Hotels.

Guest favorite

Casa particular in Logan Square

4.85 out of 5 average rating, 137 reviews

Aparthouse for 2 people maximum, comfortable and clean, very central with multiple access roads, urban transport and proximity to the train station, variety of restaurants and shops.

Enjoy the simplicity of this accommodation located in a very central and quiet area, with easy access and very nice people. In addition to this, it has a variety of shops and restaurants nearby. We are very interested in the cleanliness for the greatest comfort. Vehicles are parked on the street at no cost.

Superhost

Hotel room in The Loop

4.5 out of 5 average rating, 6 reviews

Staypineapple Chicago, Queen Mobility Acc w/Tub

We know the difficulties of deciding where to eat and what to do in one of the world’s most happening cities. But with the posh comfort and convenience of the Staypineapple in central Chicago, choosing where to stay will be easy. An amenity fee with tax ($29.29 per day) will be charged upon arrival.