Hotel vacation rentals in Chicago

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Top-rated hotel rentals in Chicago

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Guest favorite

Hotel room in The Loop

4.88 out of 5 average rating, 107 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.

Hotel room in River North

4.55 out of 5 average rating, 67 reviews

Sonder at Found Chicago | Double Bunk Room

Welcome to Found Chicago — your stylish space behind the midnight black-brick exterior and expansive bow windows. Inside, each room includes a Roku TV and eco-friendly shower essentials. Let this be your base to explore River North. Enjoy the city's history through its remarkable greystone architecture and classic Chicago bites. The Magnificent Mile is a few minutes away and has everything from upscale shopping to historic landmarks. Experience the best of The Windy City at Found Chicago.

Superhost

Hotel room in Wicker Park

4.78 out of 5 average rating, 144 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 in Near North Side

4.82 out of 5 average rating, 114 reviews

Gritty Chic River North + ACME Hotel

If you've never been one for convention, ACME is the right choice for you. Located 2 ½ blocks from the Magnificent Mile in the River North neighborhood, ACME is downtown Chicago's lifestyle boutique hotel alternative for the tragically hip. If you appreciate an eye for design and dig a high-tech vibe, you'll feel right at home in this trendy, but inviting hotel. We want your experience at ACME to blow your mind, not your budget, book a room, and be prepared to fall in love.

Hotel room in River North

4.54 out of 5 average rating, 1,248 reviews

Godfrey Hotel Lifestyle Rooftop 4.5*-King Deluxe

The striking, Cubist-style façade makes a statement in Chicago’s vibrant, River North district. The rooftop lounge is one of the city’s best and operates year-round. We do not charge cleaning fees, however, an urban fee of $20 per night (plus taxes) will be applied. This fee is not included in the price you paid to Airbnb and will be due upon check out. A description of this fee is available on the hotel website. An incidental hold of $100.00 per night is required.

Shared hotel room in Near North Side

4.52 out of 5 average rating, 1,764 reviews

Traveler's Dream - 1 bed in a shared bedroom

Join us at Freehand Chicago Hotel for your travels in Chicago. Perfect for travelers here too long for a traditional hotel or for just 1 night; make us your home away from home. This listing is for one bunk for one person in a shared mixed/co-ed room with 4 bunks (up to 3 roommates). We have many options such as private standard rooms and private quad rooms. Please send us a message with any questions. $5 nightly resort fee plus tax paid at the property

Superhost

Private room in Irving Park

4.73 out of 5 average rating, 49 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 Plainfield

5 out of 5 average rating, 6 reviews

Vaughan Suite - The Plainfield Inn

Stay in an upscale place that’s near everything you want to visit.APPROX. 204 sq ft. · PRIVATE BATH · SOUTHERN EXPOSURE This is the second largest room in the South building with a queen bed, private bathroom, and southern exposure. It is named for the past owner of the building and who started Vaughan dance academy in historic downtown Plainfield and was then remodeled to match the charm of the historical hotel !

Superhost

Hotel room in Magnificent Mile

4.53 out of 5 average rating, 118 reviews

Classic luxury on iconic Michigan Ave

Resort fee of $23.48 per night collected by hotel. The Millennium Knickerbocker Hotel Chicago, located near the famous Magnificent Mile, is a blend of classic Chicago style and rich history. Established in 1927, it has served as a Penthouse casino and speakeasy, with traces of its iconic past still evident. The hotel is committed to providing 4-star service throughout your stay.

Superhost

Hotel room in The Loop

4.78 out of 5 average rating, 54 reviews

A polished, modern affair on iconic Michigan Ave.

Resort fee of $15.00 per night collected by hotel. Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.

Guest favorite

Hotel room in Wicker Park

4.91 out of 5 average rating, 46 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 favorite

Casa particular in Logan Square

4.83 out of 5 average rating, 115 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.