Five Star Hotels in Southwest Side

    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
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Southwest Side 5 Star Hotels

Next weekend
In two weeks

Top Southwest Side 5 Stars Hotels

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1002)
"Amazing service!! Beautiful hotel!"
The price is RM2,645
RM3,105 total
includes taxes & fees
29 Jun - 30 Jun
The Peninsula Chicago

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1001)
"I had such a lovely staycation, and I recommend a stay here to everyone I know. "
The price is RM2,283
RM2,680 total
includes taxes & fees
27 Jul - 28 Jul
The Langham, Chicago

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (999)
"great hotel and close to all the activite"
The price is RM2,243
RM2,633 total
includes taxes & fees
6 Jul - 7 Jul
Four Seasons Hotel Chicago

Trump International Hotel & Tower Chicago

5.0 star property
9.4 out of 10, Exceptional, (1625)
"Great hotel with great staff."
The price is RM1,984
RM2,329 total
includes taxes & fees
6 Jul - 7 Jul
Trump International Hotel & Tower Chicago

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1000)
"The room service and overall staff at this property is excellent "
The price is RM2,249
RM2,640 total
includes taxes & fees
6 Jul - 7 Jul
Waldorf Astoria Chicago

Nobu Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (680)
"We had an excellent experience staying at the Nobu and was treated like royalty!"
The price is RM1,436
RM1,685 total
includes taxes & fees
29 Jun - 30 Jun
Nobu Hotel Chicago

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1000)
"Superb customer service, clean hotel!"
The price is RM2,264
RM2,658 total
includes taxes & fees
6 Jul - 7 Jul
Park Hyatt Chicago

The St. Regis Chicago

5.0 star property
9.0 out of 10, Wonderful, (68)
"Excellent service! Always a great time! "
The price is RM2,421
RM2,842 total
includes taxes & fees
13 Jul - 14 Jul
The St. Regis Chicago

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1001)
"Best hotel in Chicago "
The price is RM2,015
RM2,365 total
includes taxes & fees
27 Jul - 28 Jul
The Ritz-Carlton, Chicago

Art Villa

5.0 star property
The price is RM2,112
RM3,622 total
includes taxes & fees
9 Jul - 10 Jul
Art Villa
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 Southwest Side.
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.
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.

Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport