Top 10 Hotels in Southwest Side (from $71) 2026 - Competitive Prices

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Our top choices for Southwest Side hotels

A modern bar area with a bar counter, seating, and large windows offering a view of the street.

A modern lobby with a vending machine, a statue, and an exit sign.

A modern bar area with a curved counter, multiple stools, and pendant lighting. A menu board is visible on the wall, and a coffee machine is on the counter.

A reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

$141 nightly

$164 total

Nov 3 - Nov 4

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.

A breakfast bar with coffee makers, a toaster, and a variety of pastries.

A modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.

A reception area with a wooden reception desk, a sofa, and a coffee table.

2. Carlton Inn Midway

Archer Heights

Icaro

$119 nightly

$140 total

Oct 6 - Oct 7

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.

A compact kitchen with a dining table and chairs, a built-in oven, and a refrigerator.

A small bathroom with a white sink, a mirror, and a window with an air conditioning unit.

A compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

3. Rainbow Motel

Garfield Ridge

Jerry

$93 nightly

$109 total

Oct 6 - Oct 7

Total with taxes and fees

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

A residential street with a sidewalk, houses, and greenery.

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

4. Carleton of Oak Park

Oak Park

Brad

$114 nightly

$127 total

Oct 15 - Oct 16

Total with taxes and fees

A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

5. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

$172 nightly

$204 total

Nov 3 - Nov 4

Total with taxes and fees

A large, historic building with a central courtyard surrounded by trees.

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

6. Hilton Chicago

Downtown Chicago

Anna

$190 nightly

$226 total

Oct 30 - Oct 31

Total with taxes and fees

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

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

Downtown Chicago

Shanequa

$258 nightly

$307 total

Nov 1 - Nov 2

Total with taxes and fees

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

8. Congress Plaza Hotel

Downtown Chicago

Jessica

$106 nightly

$126 total

Nov 2 - Nov 3

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.

A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

A modern conference room with a marble table, patterned chairs, a flat-screen TV, and a large window with a view of trees and parked cars.

A spacious lobby with a modern design, featuring a seating area with sofas and chairs, a coffee table, and a large flat-screen TV mounted on the wall.

9. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

$98 nightly

$108 total

Oct 6 - Oct 7

Total with taxes and fees

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.

A compact kitchen with a microwave, coffee maker, and sink.

A restaurant with booths, tables, and a green wall in the background.

10. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$116 nightly

$138 total

Nov 2 - Nov 3

Total with taxes and fees

A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

An indoor swimming pool with clear windows, green chairs, and a tiled deck.

A reception desk with a "Welcome to the Prairie State" sign, a Hilton Honors sign, and a wooden wall with a herringbone pattern.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view.

11. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

A modern interior with wooden flooring, black furniture, and large windows offering city views.

A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

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

12. Hotel 505 River North

Downtown Chicago

Giana

$256 nightly

$304 total

Nov 2 - Nov 3

Total with taxes and fees

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

A modern restaurant interior with a long counter, booths, and tables.

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

A modern bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.

13. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Jayne

$190 nightly

$226 total

Oct 25 - Oct 26

Total with taxes and fees

A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

14. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$189 nightly

$224 total

Oct 25 - Oct 26

Total with taxes and fees

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

A modern lounge area with seating, a bar, and large windows offering views.

A modern gym with various exercise equipment, large windows, and a city view.

A modern interior with a long counter, glass partitions, and a brick wall backdrop.

15. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

$193 nightly

$229 total

Nov 1 - Nov 2

Total with taxes and fees

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

A restaurant with outdoor seating, covered by umbrellas, and decorated with hanging planters.

A bar area with a large mural, bar stools, and a variety of bottles and glasses on the counter.

A modern hotel room with a large bed, a desk, a chair, a lamp, and a view of the city through large windows.

16. Le Méridien Essex Chicago

Downtown Chicago

Kayla Rene

$247 nightly

$294 total

Oct 31 - Nov 1

Total with taxes and fees

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

A hotel room with two beds, a window with curtains, a bedside table with a lamp, and a small ottoman.

A laundry area with a washing machine, a dryer, and an ice dispenser.

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

17. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

$128 nightly

$152 total

Nov 2 - Nov 3

Total with taxes and fees

A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.

A modern building with large glass windows and a covered walkway.

A grand lobby with ornate ceiling artwork, chandeliers, and a prominent 'P' emblem.

A grand hall with a central aisle, ornate chandeliers, and rows of chairs.

18. Palmer House a Hilton Hotel

Downtown Chicago

Sydney

$215 nightly

$256 total

Oct 31 - Nov 1

Total with taxes and fees

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

A hotel room with a large bed, a desk with a chair, a sofa, and a TV.

A gym with cardio machines, weight benches, and a large window offering a city view.

A modern hotel room with a large window, a desk with a lamp, a sofa, and a chair.

19. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

$195 nightly

$232 total

Nov 1 - Nov 2

Total with taxes and fees

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

A modern bar area with a central bar, seating, and a distinctive ceiling design.

A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

20. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

$199 nightly

$237 total

Oct 31 - Nov 1

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.

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Balzekas Museum of Lithuanian Culture

10.0/10 (1 review)

You can spend time exploring the galleries in Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area, or check out its top-notch restaurants.

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Union Stock Yard Gate

You can find out about the history of Chicago with a trip to Union Stock Yard Gate.

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S.S. Peter and Paul Church

After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

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Ephraim Bajar Cultural Center

Enjoy an outing to Ephraim Bajar Cultural Center during your stay in Chicago. Amble around the area's parks or visit its churches.

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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

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Mom & daughter trip to meet in Chicago to see a concert. Lovely property in a good location to get everywhere we needed. Felt safe walking around day & night as needed."

Hilton Chicago

8/10 Good

"Solid 4 out of 5 star hotel. Great location and helpful staff. No room service keeps it from 5 star territory."

Congress Plaza Hotel

10/10 Excellent

"If you’re going to a bears game this place is amazing. About a 25 minute walk not horrible, bed was comfortable room was clean. Not haunted at all despite the rumors. Overall a great experience."

Hotel Riu Plaza Chicago

10/10 Excellent

"We had a good experience, nothing to complain!"

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Good place"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Clean sensible hotel. Can’t beat location."

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Really nice place"

Sports Illustrated Resorts Chicago

8/10 Good

"Nice room and great location…need a restaurant and real bar-bar is sort of open…would like to see it after they really rebrand everything"

Hyatt Regency Chicago

10/10 Excellent

"The room was spacious and the bed was very comfortable. The check in was easy and they gave us a voucher for a drink in the lounge bar. We had a very nice stay. Great location, the river walk is with in walking distance."

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

$62 nightly

$71 total

Oct 14 - Oct 15

Total with taxes and fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 12 - Oct 13

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$98 nightly

$108 total

Oct 6 - Oct 7

Total with taxes and fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$109 nightly

$130 total

Nov 1 - Nov 2

Total with taxes and fees

8/10 Very Good! (1,653 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$116 nightly

$138 total

Nov 2 - Nov 3

Total with taxes and fees

7.8/10 Good! (2,885 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

Hotels in Southwest Side with star-rating

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Things to do in Chicago

Find hotels in Southwest Side, IL from $71

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in Southwest Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Southwest Side hotels

1. Holiday Inn Chicago – Midway Airport S by IHG

2. Carlton Inn Midway

3. Rainbow Motel

4. Carleton of Oak Park

5. Hilton Vacation Club Hotel Blake Chicago

6. Hilton Chicago

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

8. Congress Plaza Hotel

9. SureStay Plus Hotel by Best Western Chicago Lombard

10. Travelodge by Wyndham Downtown Chicago

11. Hampton Inn Chicago-O'Hare International Airport

12. Hotel 505 River North

13. Homewood Suites by Hilton Chicago Downtown South Loop

14. Hilton Garden Inn Chicago Downtown South Loop

15. Hyatt House Chicago/West Loop-Fulton Market

16. Le Méridien Essex Chicago

17. Hotel Saint Clair- Magnificent Mile

18. Palmer House a Hilton Hotel

19. Hyatt Place Chicago/Downtown - The Loop

20. Fairmont Chicago at Millennium Park

Stay near popular Southwest Side attractions

Marquette Park

Balzekas Museum of Lithuanian Culture

Union Stock Yard Gate

S.S. Peter and Paul Church

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Hilton Chicago

Congress Plaza Hotel

Hotel Riu Plaza Chicago

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

InterContinental Chicago Magnificent Mile by IHG

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Sports Illustrated Resorts Chicago

Hyatt Regency Chicago

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

Red Roof Inn PLUS+ Chicago - Willowbrook

SureStay Plus Hotel by Best Western Chicago Lombard

Hampton Inn Chicago Downtown/Magnificent Mile

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago-O'Hare International Airport

Hotels in Southwest Side with star-rating

Explore a world of travel with Expedia

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