Hotel holiday rentals in Chicago

Find and book unique hotel rentals on Airbnb

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 in Wicker Park

4.77 out of 5 average rating, 133 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.

23–30 May

$472 SGD per night

Superhost

Boutique hotel in Near North Side

4.81 out of 5 average rating, 107 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.

30 Sep – 7 Oct

$334 SGD per night

Boutique hotel in The Loop

4.77 out of 5 average rating, 152 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.

21–26 May

$429 SGD per night

Hotel in Chicago

4.64 out of 5 average rating, 115 reviews

Godfrey Hotel Lifestyle Rooftop 4.5*-Double 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.

9–16 Dec

$139 SGD per night

Shared hotel room in Chicago

4.53 out of 5 average rating, 1691 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

3–10 Aug

$104 SGD per night

Superhost

Room in Irving Park

4.78 out of 5 average rating, 41 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. In this unit you share the living room, kitchen and bathroom when renting only one private bedroom.

7–14 Jul

$119 SGD per night

Superhost

Hotel in Magnificent Mile

4.65 out of 5 average rating, 43 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.

16–23 Jul

$214 SGD per night

Superhost

Hotel in Chicago

4.8 out of 5 average rating, 41 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.

12–19 May

$440 SGD per night

Superhost

Hotel in Chicago

4.88 out of 5 average rating, 16 reviews

Sweeping skyline views from the 40th floor

Resort fee of $12.86 per night collected by hotel. The moment you step into your spacious ‘home away from home’ on our 40th floor, you’re sure to envelope yourself in a view that takes your breath away. Our Deluxe King room offers lofty ceilings, an oversized marble tub, and wet bar- for your enjoyment.

29 Jul – 5 Aug

$531 SGD per night

Superhost

Boutique hotel in Chicago

4.73 out of 5 average rating, 413 reviews

Staypineapple Chicago, Deluxe 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 ($23.42 per day) will be charged upon arrival.

3–10 Jan

$296 SGD per night

Guest favourite

Casa particular in Chicago

4.82 out of 5 average rating, 105 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 cleanliness for added comfort. Vehicles are parked on the street at no cost.

29 Sep – 6 Oct

$135 SGD per night

Guest favourite

Boutique hotel in Plainfield

4.91 out of 5 average rating, 35 reviews

Spangler Suite - The Plainfield Inn

APPROX. 16 X 12 · PRIVATE BATH · NORTH AND EASTERN EXPOSURE This is the largest room in the original house with northern and eastern exposures. It is named for the original building owner who moved the 1851 school-house to Fox River where it now sits.

15–20 Jun

$193 SGD per night