Hotel holiday rentals in Downtown Chicago

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.

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.

$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.

A polished, modern affair on iconic Michigan Ave.

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. The perfect location that is just steps away from Grant Park where Lollapalooza 2025 will be held!

Light-flooded rooms and city views

The Hoxton, Chicago feels like a home away from home, with its comfy hotel rooms, great food and a rooftop to soak up some rays in the heart of Fulton Market District, one of Chicago's most creative neighborhoods. All rooms come with mid-century furnishings, modern bathrooms, and warehouse-style floor-to-ceiling windows to show off Chicago in full. Just 2.2 miles from Grant Park where Lollapalooza 2025 will be held!

All-glass gem by Chicago architect Harry Weese

$29.35 Resort Fee to be collected on property Swissotel Chicago is an award-winning luxury hotel overlooking the Chicago River and Lake Michigan, and just steps from the Magnificent Mile. The distinctive 4-diamond, all-glass hotel offers spectacular wrap-around views from Navy Pier to Millennium Park and has a state-of-the-art penthouse fitness center. Close to Grant Park which will host Lollapalooza 2025!

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.

Sweeping skyline views from the 40th floor

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. Just 5 blocks from Grant Park where Lollapalooza will be held!

Studio apartment for 2 people maximum, comfortable and clean, very central with multiple access roads, urban transport and proximity to the train station, a 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 the utmost convenience. Vehicles are parked on the street at no cost.