Hotel vacation rentals in Near North Side, Chicago

Hotel in The Loop

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 Wicker Park

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.

Aug 29 – Sep 5

Boutique hotel in Magnificent Mile

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 23 – 30

Hotel in River North

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.

Dec 2 – 9

Shared hotel room in Near North Side

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

Jan 18 – 25

Room in Chicago

$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 25 – Aug 1

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.

Jul 14 – 21

Hotel in The Loop

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.

May 24 – 31

Hotel room in Wicker Park

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.

Dec 11 – 18