5 Star Hotels in Southwest Side, Chicago

Start date: Check-in selected.
To Date
End date: Check-out
    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, (1745)
"Beautiful hotel centrally located"
The price is €463
includes taxes & fees
5 Oct - 6 Oct
Trump International Hotel & Tower Chicago
The Langham, Chicago
Lobby

The Langham, Chicago

5.0 star property
9.8 out of 10, Exceptional, (1011)
"Great place to stay. "
The price is €545
includes taxes & fees
26 Oct - 27 Oct
The Langham, Chicago
The Peninsula Chicago
Front of property – evening/night

The Peninsula Chicago

5.0 star property
9.8 out of 10, Exceptional, (1013)
"Amazing hotel will be back for sure!"
The price is €597
includes taxes & fees
26 Oct - 27 Oct
The Peninsula Chicago
Four Seasons Hotel Chicago
Reception

Four Seasons Hotel Chicago

5.0 star property
9.4 out of 10, Exceptional, (1006)
"Amazing hotel"
The price is €577
includes taxes & fees
5 Oct - 6 Oct
Four Seasons Hotel Chicago
Waldorf Astoria Chicago
Exterior

Waldorf Astoria Chicago

5.0 star property
9.4 out of 10, Exceptional, (1006)
"Simply love this hotel"
The price is €579
includes taxes & fees
5 Oct - 6 Oct
Waldorf Astoria Chicago
Park Hyatt Chicago
Suite, Terrace (Water Tower)

Park Hyatt Chicago

5.0 star property
9.6 out of 10, Exceptional, (1003)
"beautiful room and hotel great bar!"
The price is €627
includes taxes & fees
28 Sept - 29 Sept
Park Hyatt 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, (729)
"Great location, amenities and staff. "
The price is €493
includes taxes & fees
2 Oct - 3 Oct
Nobu Hotel Chicago
The Ritz-Carlton, Chicago
Bar (on property)

The Ritz-Carlton, Chicago

5.0 star property
9.2 out of 10, Wonderful, (1007)
"Beautiful place "
The price is €627
includes taxes & fees
5 Oct - 6 Oct
The Ritz-Carlton, Chicago
The St. Regis Chicago
2 restaurants, breakfast served

The St. Regis Chicago

5.0 star property
9.2 out of 10, Wonderful, (77)
"Nice place "
The price is €627
includes taxes & fees
5 Oct - 6 Oct
The St. Regis Chicago
Art Villa
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
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.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL
The price is €187 per night from 5 Oct to 6 Oct
€187
5 Oct - 6 Oct
includes taxes & fees
8.4/10 Very Good! (4,985 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 Union Stock Yard Gate 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

Explore a world of travel with Expedia

Explore a world of travel with Expedia