Hotel holiday 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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Superhost

Hotel room

4.77 out of 5 average rating, 199 reviews

Hotel Quality Meets Local Living Deluxe Studio 3B

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. Note there are no TV's in rooms and no elevator.

Superhost

Hotel room

4.79 out of 5 average rating, 165 reviews

Spacious Hotel Room in The Loop

Just steps away from the famed shopping on State Street, this boutique hotel is located inside the Nederlander Theater building in the Chicago Loop Theater District. The hotel features on-site dining, state-of-the-art business services and modern guest rooms with free WiFi. Every room at Cambria Hotel Chicago Loop/Theater District provides a 49-inch flat-screen HDTV and a large work space with a desk and ergonomic chair. Select rooms also offer plush lounge seating.

Superhost

Hotel room

4.78 out of 5 average rating, 9 reviews

Close To Chicago O'Hare Airport | Free Breakfast

Welcome to our Residence Inn Chicago O'hare Hotel, located near the Chicago OHare Airport, winner of the 2021 Trip Advisor Travelers Choice Hotel. Guests can enjoy complimentary shuttle service to and from the airport. Start your day with our complimentary hot breakfast buffet served daily or a quick workout in the fitness center. Attractions are near the Residence Inn Chicago OHare and we are also within walking distance of corporate headquarters.

Superhost

Private room

4.72 out of 5 average rating, 65 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

4.95 out of 5 average rating, 21 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.

Hotel room

4.77 out of 5 average rating, 196 reviews

Standard Double Hotel Room at Magnificent Mile

Welcome to St. Clair Hotel Chicago Magnificent Mile! The St. Clair Hotel - Magnificent Mile is conveniently located in the heart of Chicago, the city that ranks high on top travel & tourism lists year after year! We are steps away from shopping along the Magnificent Mile as well as close to exploring the city’s biggest attractions including Lincoln Park Zoo, 360 Chicago Observatory, Navy Pier, and the Chicago Theatre.

Guest favourite

Hotel room

4.95 out of 5 average rating, 135 reviews

Relaxing Standard Room l Free Airport Shuttle

Explore the charming neighborhood of Rosemont just outside our doors. Attractions await you: ✔ Offers a 24-hour front desk, airport transfers, an ATM and free WiFi throughout the property. ✔ Enjoy indoor pool or use the business centre that offers printing, copying and fax services. ✔ Breakfast included. Monday to Friday from 6:30AM to 9:30AM, and on Saturday and Sunday from 7:30AM to 10:30AM.

Superhost

Hotel room

4.69 out of 5 average rating, 35 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.

Guest favourite

Hotel room

4.91 out of 5 average rating, 66 reviews

King Room in Boutique Wicker Park B&B

Modern guest room located on the main floor just a block away from great dining, vintage and boutique shopping, art galleries, cool cafes and vibrant nightlife. The Ellen King guest room is one of 9 rooms within the Wicker Park Inn, a newly renovated, boutique Bed and Breakfast offering high quality yet affordable accommodations in a hip & trendy neighborhood.

Guest favourite

Hotel room

4.86 out of 5 average rating, 7 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.

Guest favourite

Casa particular

4.86 out of 5 average rating, 143 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

4.73 out of 5 average rating, 436 reviews

Staypineapple Chicago, Burnham King

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.