5 Star Hotels in Southwest Side, Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Southwest Side 5 Star Hotels

Top Southwest Side 5 Star Hotels

Trump International Hotel & Tower Chicago
Bar (on property)

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1677)
"Great hotel "
The price is €464
includes taxes & fees
7 Sept - 8 Sept
Trump International Hotel & Tower Chicago
Four Seasons Hotel Chicago
Reception

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (999)
"Great location "
The price is €533
includes taxes & fees
1 Sept - 2 Sept
Four Seasons Hotel Chicago
The Langham, Chicago
Lobby

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1006)
"Location can’t be beat. Hotel is excellent! "
The price is €547
includes taxes & fees
2 Sept - 3 Sept
The Langham, Chicago
The Peninsula Chicago
Front of property – evening/night

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1003)
"Excellent very clean Quiet great location"
The price is €628
includes taxes & fees
1 Sept - 2 Sept
The Peninsula Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1000)
"Great location "
The price is €534
includes taxes & fees
24 Aug - 25 Aug
Waldorf Astoria Chicago
Nobu Hotel Chicago
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (708)
"Beautiful, staffed with great people."
The price is €462
includes taxes & fees
25 Aug - 26 Aug
Nobu Hotel Chicago
Park Hyatt Chicago
Suite, Terrace (Water Tower)

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1000)
"It's a beautiful and comfortable hotel."
The price is €618
includes taxes & fees
24 Aug - 25 Aug
Park Hyatt Chicago
The Ritz-Carlton, Chicago
Bar (on property)

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1001)
"Beautiful place "
The price is €578
includes taxes & fees
1 Sept - 2 Sept
The Ritz-Carlton, Chicago
The St. Regis Chicago
2 restaurants, breakfast served

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (72)
"Amazing hotel"
The price is €596
includes taxes & fees
2 Sept - 3 Sept
The St. Regis Chicago
Art Villa
Rooftop terrace

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is €730
includes taxes & fees
17 Aug - 18 Aug
Art Villa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Southwest Side.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL
The price is €196 per night from 4 Sept to 5 Sept
€196
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,849 reviews)
Still don't see what you're looking for?
See all properties in Southwest Side.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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 Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and S.S. Peter and Paul Church as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews