A curved pathway with a metal fence, flowering trees, and a street lamp.

Compare and book 5 Star hotels in Northwest Side, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Northwest Side 5 Star Hotels

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Northwest Side 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.
A modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.
A couple walking through a spacious lobby with marble flooring, large white floral arrangements, and a modern staircase in the background.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Edda
£455
includes taxes & fees
15 Nov - 16 Nov
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.
A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
A modern hotel room with large floor-to-ceiling windows offering a city view.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Cecille
£413
includes taxes & fees
8 Nov - 9 Nov
Trump International Hotel & Tower Chicago
A modern hotel room with a large window offering a city view, a sofa, a small table with a vase, and a lamp.
A modern dining area with round tables, comfortable chairs, and a dessert display.
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
£470
includes taxes & fees
15 Nov - 16 Nov
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A modern indoor pool area with large windows, potted palm plants, and lounge chairs.
A rooftop bar with seating and a view of the city skyline at night.
A modern bar area with a checkered floor, bar stools, and a bartender.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Melinda
£560
includes taxes & fees
15 Nov - 16 Nov
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.
A bar area with a polished marble floor, bar stools, a counter with bottles, and a decorative lamp.
A bar area with a long counter, multiple stools, and a seating area with a booth.
An indoor swimming pool with a modern design, a reception area with a sign for Waldorf Astoria Chicago, and a seating area with two people.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Luis
£470
includes taxes & fees
15 Nov - 16 Nov
Waldorf Astoria Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.
A rooftop terrace with a view of a city skyline at dusk.
A modern lobby with a sofa, a coffee table, and a vase of flowers.
A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
£428
includes taxes & fees
1 Nov - 2 Nov
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.
A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
A woman sitting by a window with a city view, holding a cup and saucer.
A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.

7. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
£477
includes taxes & fees
15 Nov - 16 Nov
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
A spacious lobby with a central seating area, a reception desk, and a large chandelier.
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.
A modern lobby with a central seating area, large windows, and a decorative ceiling feature.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Fred
£417
includes taxes & fees
15 Nov - 16 Nov
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.
A dining area with wicker chairs and tables, overlooking a marina with boats and a Ferris wheel.
A modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
£499
includes taxes & fees
12 Nov - 13 Nov
The St. Regis Chicago
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Northwest Side.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
£137
1 Nov - 2 Nov
includes taxes & fees
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
£128
3 Nov - 4 Nov
includes taxes & fees
8/10 Very good! (2,502 reviews)
The Chicago Hotel Collection Ambassador Gold Coast
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL
£157
25 Oct - 26 Oct
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Still don't see what you're looking for?
See all properties in Northwest Side.
You can also use these popular filters to refine your search.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Northwest Side

Check out the local area in Northwest Side—home to attractions like Walt Disney House and Milwaukee Avenue.

See all hotels in Northwest Side
A curved pathway with a metal fence, flowering trees, and a street lamp.

Top Northwest Side Hotel Reviews

Find out more about Northwest Side

Explore a world of travel with Expedia