Hotel vacation rentals in North Side

Boutique hotel in Near North Side

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.

Sep. 30 – Oct. 7

Boutique hotel in The Loop

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

Hotel in Chicago

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.

Jan. 26 – Feb. 2

Room in Irving Park

$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.

Jul. 16 – 23

Hotel in Magnificent Mile

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.

May 9 – 16

Hotel in Chicago

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.

Jun. 8 – 15

Hotel in Chicago

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.

Jun. 13 – 20

Boutique hotel in Chicago

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.

Dec. 10 – 17

Boutique hotel in Plainfield

Herrington Suite - The Plainfield Inn

APPROX. 11 X 11 · PRIVATE BATH · NORTHERN EXPOSURE This is the last room in the original house with northern exposure. It is named for the Goodson's daughter who married Robert Herrington. She moved back into the home in 1908 when they inherited the property.