5 Stars Hotels in Northwest Side, Chicago from CA $474

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 12 - Nov 13
Tomorrow
Nov 13 - Nov 14
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Northwest Side 5-star hotels

A group of people on a boat with a city skyline in the background.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (999 reviews)
"Great place to stay in Chicago!"
United States
ryan
The price is CA $606
CA $720 total
includes taxes & fees
Dec 13 - Dec 14
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,073 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is CA $561
CA $667 total
includes taxes & fees
Dec 13 - Dec 14
Trump International Hotel & Tower Chicago
A rooftop bar with seating and a view of the city skyline at night.

3. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,000 reviews)
"Always an incredible hotel! Definitely one of the best in the USA"
United States
Vincent Haley
The price is CA $748
CA $890 total
includes taxes & fees
Dec 13 - Dec 14
The Peninsula Chicago
A view from a window overlooking a cityscape with a river, featuring a sofa and a table with a bottle and a glass.

4. The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,009 reviews)
"Amazing hotel, best location"
United States
Talia
The price is CA $620
CA $737 total
includes taxes & fees
Dec 13 - Dec 14
The Langham, Chicago
A bar area with a polished marble floor, bar stools, a counter with bottles, and a decorative lamp.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Very clean and upscale property. Lovely amenities. Great location and staff very friendly."
United States
Loai
The price is CA $623
CA $741 total
includes taxes & fees
Dec 13 - Dec 14
Waldorf Astoria Chicago
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.

6. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
"Very helpful staff good for families"
United States
Krikour
The price is CA $529
CA $629 total
includes taxes & fees
Dec 13 - Dec 14
The Ritz-Carlton, Chicago
A modern building with the name "NOBU" illuminated on the facade.

7. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (966 reviews)
"The wellness center was my favorite!"
United States
Mauro
The price is CA $475
CA $600 total
includes taxes & fees
Nov 26 - Nov 27
Nobu Hotel Chicago
A wine cellar with wooden racks of wine bottles, a long table, and hanging lights.

8. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
"Nice clean hotel in a great location."
United States
Tom
The price is CA $606
CA $720 total
includes taxes & fees
Dec 13 - Dec 14
Park Hyatt Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (136 reviews)
"Gorgeous and family friendly"
United States
Alise
The price is CA $802
CA $954 total
includes taxes & fees
Dec 3 - Dec 4
The St. Regis Chicago

Top Northwest Side Hotel Reviews

A modern building with the name "NOBU" illuminated on the facade.
Nobu Hotel Chicago

Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago

10/10 Excellent

incredible staff and stay here. The team here crushed it and the rooms were fantastic
Canada
Jordan
Reviewed August 12, 2026
Nobu Hotel Chicago

Find out more about Northwest Side

Luxury is the name of the game at the best 5 Stars hotels in Northwest Side. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Northwest Side 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them.

Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Northwest Side hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Northwest Side without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Northwest Side.

Explore a world of travel with Expedia