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Our top choices for Southwest Side hotels

A modern bar area with a curved counter, multiple stools, and pendant lighting.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Dorsy

$115 nightly

Dec 6 - Dec 7

Total with taxes and fees

A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.

2. Carlton Inn Midway

Archer Heights

Hubert

$107 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern hotel room with a large bed, a flat-screen TV mounted on the ceiling, and a nightstand with a lamp.

3. Rainbow Motel

Garfield Ridge

Kendall

$84 nightly

Nov 15 - Nov 16

Total with taxes and fees

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Kanokkan

$111 nightly

Dec 10 - Dec 11

Total with taxes and fees

A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

5. Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Bonnie

$160 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern hotel lobby with seating areas, a reception desk, and an elevator.

6. Best Western Grant Park Hotel

Downtown Chicago

Michelle

$86 nightly

Dec 7 - Dec 8

Total with taxes and fees

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

7. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$97 nightly

Nov 24 - Nov 25

Total with taxes and fees

A modern kitchen with a large window, a dining area, and a view of the sea.

8. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Nicole

$105 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

9. Le Méridien Essex Chicago

Downtown Chicago

Taso

$127 nightly

Dec 7 - Dec 8

Total with taxes and fees

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

10. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

ALVIN

$89 nightly

Nov 12 - Nov 13

Total with taxes and fees

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

11. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Carole

$125 nightly

Nov 25 - Nov 26

Total with taxes and fees

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

12. Hotel 505 River North

Downtown Chicago

Melvin

$166 nightly

Dec 9 - Dec 10

Total with taxes and fees

A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.

13. Hilton Chicago

Downtown Chicago

Jordan

$162 nightly

Nov 26 - Nov 27

Total with taxes and fees

A modern interior with a dining area, sofas, and artwork on the walls.

14. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Grace

$88 nightly

Dec 9 - Dec 10

Total with taxes and fees

A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

15. Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

Alicia

$114 nightly

Nov 23 - Nov 24

Total with taxes and fees

A multi-story building with a prominent curved glass facade, surrounded by other high-rise buildings.

16. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Serge

$130 nightly

Nov 24 - Nov 25

Total with taxes and fees

A multi-story hotel with a prominent sign reading "Crowne Plaza."

17. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Dejai

$115 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern hotel with a glass facade, multiple floors, and a visible entrance.

18. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

maribeth

$118 nightly

Nov 23 - Nov 24

Total with taxes and fees

A cozy room with a sofa, a dining table, and a window with a view of buildings.

19. LIVN - West Loop Chicago

Downtown Chicago

Elzbieta

$132 nightly

Nov 15 - Nov 16

Total with taxes and fees

A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

20. La Quinta Inn & Suites by Wyndham Chicago Downtown

Downtown Chicago

Andres

$114 nightly

Nov 23 - Nov 24

Total with taxes and fees

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Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

See properties

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

"Excellent stay! Will definitely seek this property out again for my stay in Chicago"

Congress Plaza Hotel

8/10 Good

"Honestly not my favorite stay, but it was in a super convenient location. We stayed three nights, and checked in pretty late. The hotel is very old in a sense of no modern amenities, no microwave in the room but has a great and comfortable vintage aesthetic. Was also told that it’s haunted with lore of a little ghost boy roaming the halls of the 10th floor.. lol. Staff and security were super friendly and great to converse with about things to do in the city. Would I stay again? Probably not, but wasn’t the worst place to stay."