Boutique hotel vacation rentals in Chicago Loop

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Top-rated boutique hotel rentals in Chicago Loop

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Boutique hotel in River North

4.55 out of 5 average rating, 65 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.

Jun 17 – 24

R4,264 ZAR per night

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.

Oct 24 – 31

R2,163 ZAR per night

Superhost

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.

Aug 28 – Sep 4

R3,901 ZAR per night

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.

May 21 – 26

R5,734 ZAR per night

Shared hotel room in Near North Side

4.52 out of 5 average rating, 1698 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

Mar 9 – 16

R425 ZAR per night

Boutique hotel in The Loop

4.39 out of 5 average rating, 408 reviews

Standard King Room

The Standard King Rooms feature one King bed as well as a decorative round table and two chairs. Amenities include: Complimentary wireless Internet, Coffeemaker and coffee, Iron/ironing board, Mini refrigerator, Pillowtop beds , Hairdryer, Room service, Flat-screen TV with cable and satellite channels and a Safe deposit box. Heating and Air condition based on temperature out side

Jan 29 – Feb 5

R1,889 ZAR per night

Superhost

Boutique hotel in Near North Side

4.81 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 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.

Jul 21 – 28

R4,416 ZAR per night

Superhost

Boutique hotel in Near North Side

4.79 out of 5 average rating, 67 reviews

Gritty Chic River North + ACME Hotel

Aug 24 – 31

R5,054 ZAR per night

Superhost

Boutique hotel in The Loop

4.73 out of 5 average rating, 112 reviews

Staypineapple Chicago, Deluxe Queen

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.

Nov 30 – Dec 7

R3,850 ZAR per night