Hotel vacation rentals in Chicago Loop

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Top-rated hotel rentals in Chicago Loop

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Hotel in River North

4.63 out of 5 average rating, 35 reviews

Just a short walk from Magnificent Mile! Pool!

Set in the River North neighborhood of Chicago, this property offers easy access to popular Chicago attractions, restaurants, and shopping. Head to Navy Pier, Willis Tower, or Wrigley Field for iconic Chicago experiences. Shop ‘til you drops on the Magnificent Mile, which is within walking distance of the property. Experience Chicago-style pizza or Italian cuisine at a nearby restaurant. There’s so much to explore in the Windy City and it’s all just steps from this convenient downtown location.

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Hotel room in Wicker Park

4.78 out of 5 average rating, 137 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.

Boutique hotel in Magnificent Mile

4.73 out of 5 average rating, 62 reviews

Warwick Allerton Queen

Our cosy and comfortable standard rooms evoke all the charm and elegance of Warwick Allerton - Chicago’s storied past. Retaining the design of the Chicago hotel’s original single rooms, each space is filled with natural light, tastefully updated with timeless furnishings and includes a queen size bed, marble bathrooms, and unforgettable city views. Offering an enviable location in the heart of Chicago’s world-class shopping and dining district, and a view of Michigan Avenue.

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Boutique hotel in Near North Side

4.82 out of 5 average rating, 110 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.

Boutique hotel in The Loop

4.77 out of 5 average rating, 153 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.

Hotel in River North

4.54 out of 5 average rating, 1232 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 Chicago

4.52 out of 5 average rating, 1699 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

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Room in Irving Park

4.7 out of 5 average rating, 43 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.

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Hotel in Magnificent Mile

1927 gem, once home of Capone Speakeasy

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.

Hotel in River North

4.75 out of 5 average rating, 4 reviews

Onsite spa and indoor/outdoor rooftop bar

Resort fee of $23.48 per night collected by hotel. Everyday life requires us to live outside our comfort zone; outside our element. We find ourselves in surrounding places with a generalized design intent meant for mass appeal. At The Godfrey Hotel Chicago, we've created a rare spot that will make you feel entirely at ease. We offer a unique style with attention to comfort.

Guest favorite

Casa particular in Logan Square

4.82 out of 5 average rating, 107 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.

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Hotel in The Loop

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.