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Our top choices for Southwest Side 4-star hotels

A modern reception area with a check-in counter, seating, and a decorative wall.

1. Hilton Chicago O'Hare Airport

O'Hare

Cassandra L

SAR 895 total

includes taxes & fees

27 Nov - 28 Nov

A grand lobby with a central bar, high ceilings, and classical architecture.

2. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Elizabeth

SAR 531 total

includes taxes & fees

3 Dec - 4 Dec

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

3. River Hotel

Downtown Chicago

Shelby

SAR 531 total

includes taxes & fees

23 Nov - 24 Nov

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

4. The Wade

Downtown Chicago

Sara

SAR 531 total

includes taxes & fees

23 Nov - 24 Nov

A rooftop lounge with outdoor seating, a fire feature, and transparent dome structures.

5. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Silvia

SAR 466 total

includes taxes & fees

9 Nov - 10 Nov

A rooftop terrace with outdoor seating, a view of the city skyline, and a building with a brick facade.

6. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Kevin

SAR 517 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a marble island, fruit bowls, and a city view.

7. Fairmont Chicago at Millennium Park

Downtown Chicago

Eric

SAR 1,022 total

includes taxes & fees

24 Nov - 25 Nov

A multi-story building with a prominent entrance featuring a large archway and a sign.

8. Hilton Chicago

Downtown Chicago

Christian

SAR 592 total

includes taxes & fees

27 Nov - 28 Nov

A historic building with a prominent entrance, multiple flags, and a classic architectural style.

9. Warwick Allerton - Chicago

Downtown Chicago

Audrey

SAR 478 total

includes taxes & fees

18 Nov - 19 Nov

The Intercontinental hotel facade with a large American flag and a floral display.

10. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Faye

SAR 1,002 total

includes taxes & fees

22 Nov - 23 Nov

A dining area with a table set for four, large windows offering a cityscape view at dusk.

11. The Royal Sonesta Chicago Downtown

Downtown Chicago

Derrick K

SAR 718 total

includes taxes & fees

23 Nov - 24 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

12. L7 Chicago by LOTTE

Downtown Chicago

Matthew

SAR 582 total

includes taxes & fees

23 Nov - 24 Nov

13. Arlo Chicago

Downtown Chicago

Daniel

SAR 679 total

includes taxes & fees

25 Nov - 26 Nov

A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

14. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Robert

SAR 461 total

includes taxes & fees

22 Nov - 23 Nov

A modern rooftop lounge with white seating, a glass ceiling, and city views.

15. The Godfrey Hotel Chicago

Downtown Chicago

Tamiya

SAR 581 total

includes taxes & fees

24 Nov - 25 Nov

A modern interior with a central spiral sculpture, multiple levels, and seating areas.

16. Hyatt Regency O'Hare Chicago

Rosemont

Garth

SAR 615 total

includes taxes & fees

22 Nov - 23 Nov

A hotel with a prominent 'HOTEL FELIX' sign, surrounded by tall buildings and a tree-lined street.

17. Hotel Felix River North/Magnificent Mile

Downtown Chicago

Amy

SAR 572 total

includes taxes & fees

9 Nov - 10 Nov

A dining table set for six with a cityscape view through large windows.

18. Swissotel - Chicago

Downtown Chicago

Oleg

SAR 652 total

includes taxes & fees

26 Nov - 27 Nov

A long, narrow hallway with a patterned carpet, recessed lighting, and doors on one side.

19. Loews Chicago O'Hare Hotel

Rosemont

Arnulfo

SAR 620 total

includes taxes & fees

27 Nov - 28 Nov

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

20. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Lorena

SAR 753 total

includes taxes & fees

23 Nov - 24 Nov

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Explore similar 5-star hotels

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

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

SAR 1,877

SAR 2,231 total

22 Nov - 23 Nov

includes taxes & fees

9.4/10 Exceptional! (999 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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 Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side

An airport with multiple runways, parked airplanes, and a large terminal building.

Top Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Clean, has a wonderful staff. Also great bar and amenities."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"I can’t say enough about this place! Beautiful hotel in the heart of Downtown, close to everything. My only complaint was that I called to ask if there was parking other than valet and they said no. But when I got there, there’s a parking garage right next-door. However, the valet was so gracious and helpful! He met me at my car door and helped me by taking my arm full of trash and walking at half a block down to the trashcan for me. And I don’t think I ever saw a single guest open that front door on their own. The bartender was the loveliest, funniest and sweetest woman. Made everyone feel at home. The food was all Exceptional as well. Front desk staff, also friendly and welcoming. Beds were super comfy, and the blackout curtains were a plus. I will definitely stay again next time I’m in Baton Rouge."

Room 1

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Check availability on Southwest Side 4 Star Hotels

Our top choices for Southwest Side 4-star hotels

1. Hilton Chicago O'Hare Airport

2. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

3. River Hotel

4. The Wade

5. The Chicago Hotel Collection - Magnificent Mile

6. The Chicago Hotel Collection Ambassador Gold Coast

7. Fairmont Chicago at Millennium Park

8. Hilton Chicago

9. Warwick Allerton - Chicago

10. InterContinental Chicago Magnificent Mile by IHG

11. The Royal Sonesta Chicago Downtown

12. L7 Chicago by LOTTE

13. Arlo Chicago

14. Hotel Saint Clair- Magnificent Mile

15. The Godfrey Hotel Chicago

16. Hyatt Regency O'Hare Chicago

17. Hotel Felix River North/Magnificent Mile

18. Swissotel - Chicago

19. Loews Chicago O'Hare Hotel

20. LondonHouse Chicago, Curio Collection by Hilton

Explore similar 5-star hotels

Four Seasons Hotel Chicago

Trump International Hotel & Tower Chicago

The Peninsula Chicago

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

Hotel Saint Clair- Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

The Royal Sonesta Chicago Downtown

Hilton Chicago

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Find 4 Star Hotels in Southwest Side, IL from SAR 461

Change your mind

Treat yourself

Be picky

Check availability on Southwest Side 4 Star Hotels

Our top choices for Southwest Side 4-star hotels

1. Hilton Chicago O'Hare Airport

2. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

3. River Hotel

4. The Wade

5. The Chicago Hotel Collection - Magnificent Mile

6. The Chicago Hotel Collection Ambassador Gold Coast

7. Fairmont Chicago at Millennium Park

8. Hilton Chicago

9. Warwick Allerton - Chicago

10. InterContinental Chicago Magnificent Mile by IHG

11. The Royal Sonesta Chicago Downtown

12. L7 Chicago by LOTTE

13. Arlo Chicago

14. Hotel Saint Clair- Magnificent Mile

15. The Godfrey Hotel Chicago

16. Hyatt Regency O'Hare Chicago

17. Hotel Felix River North/Magnificent Mile

18. Swissotel - Chicago

19. Loews Chicago O'Hare Hotel

20. LondonHouse Chicago, Curio Collection by Hilton

Explore similar 5-star hotels

Four Seasons Hotel Chicago

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast