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 hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

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.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

$149 nightly

$173 total

Oct 25 - Oct 26

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

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

A modern living room with a grey sofa, a round coffee table, and a chair. There are framed pictures on the wall and a window providing natural light.

2. Carlton Inn Midway

Archer Heights

Icaro

$119 nightly

$140 total

Oct 12 - Oct 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.

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

A reception desk with a glass partition, a no pets allowed sign, a no smoking sign, a QR code for check-in, and a sign indicating a 1-minute wait for guests.

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 8 - Oct 9

Total with taxes and fees

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

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

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

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

4. Carleton of Oak Park

Oak Park

Brad

$109 nightly

$121 total

Oct 21 - Oct 22

Total with taxes and fees

A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.

A modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.

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

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

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

6. Hilton Chicago

Downtown Chicago

Anna

$190 nightly

$226 total

Oct 30 - Oct 31

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

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.

7. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

$89 nightly

$99 total

Oct 8 - Oct 9

Total with taxes and fees

A modern interior with a bar area, seating, and decorative wooden panels.

A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.

A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.

8. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

$161 nightly

$192 total

Oct 25 - Oct 26

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 spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

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

9. 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.

Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

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

10. Congress Plaza Hotel

Downtown Chicago

Katimah

$107 nightly

$127 total

Nov 2 - Nov 3

Total with taxes and fees

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

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

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

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

11. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$115 nightly

$135 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 living room with a sectional sofa, a fireplace, and a large window offering a city view.

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

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

12. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Jayne

$182 nightly

$216 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

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

13. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

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

A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

14. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$184 nightly

$218 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

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

A hotel lobby with a large Christmas tree, a sofa with red and white pillows, a glass coffee table, and a large window with a view of the street.

15. Hotel 505 River North

Downtown Chicago

Giana

$256 nightly

$304 total

Nov 2 - Nov 3

Total with taxes and fees

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

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

A view from a window with a cityscape in the background, including modern buildings and a clear sky.

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

16. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Joel

$193 nightly

$229 total

Nov 1 - Nov 2

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 person sitting on a blue couch with a dog beside them, holding a glass of wine, and a pizza on a wooden board on a table.

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

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

17. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

$128 nightly

$152 total

Nov 2 - Nov 3

Total with taxes and fees

An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.

A spacious indoor area with seating arrangements, large windows, and indoor plants.

A modern lobby with a sofa, coffee table, and potted plants.

A modern lounge area with a sofa, chairs, and a large potted plant.

18. The Emily Hotel

Downtown Chicago

Leslie

$204 nightly

$242 total

Nov 1 - Nov 2

Total with taxes and fees

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

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

A grand lobby with ornate ceiling artwork, a bar area, and seating arrangements.

A multi-story building with large windows, a clock, and a storefront with a sign.

19. 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 reception area with a modern design, including a reception desk, a decorative wall, and a display case with snacks.

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.

20. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

$212 nightly

$252 total

Oct 25 - Oct 26

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

River Hotel

10/10 Excellent

"Clean and very helpful staff. Great location!"

Congress Plaza Hotel

10/10 Excellent

"Everything was good , tv remote was not working it was broken. Also, their coffee maker was dirty."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Great stay for a few days. Very convenient location and close to the train. Rooftop bars are also great, shout out to the staff"

Club Quarters Hotel, Central Loop, Chicago

8/10 Good

"No fridge and pretty thin walls but a good property"

Sports Illustrated Resorts Chicago

10/10 Excellent

"Absolutely loved it! Staff were all so nice and helpful. So closed to everything! River walk, The Bean, Chicago theater, Hello Kitty cafe, London House rooftop, Michigan Ave, you can also get The Wendella boat tour just walking distance as well, definitely staying here again!"

The Godfrey Hotel Chicago

10/10 Excellent

"The staff had a great attitude, and the bartenders were incredibly nice and welcoming. They even gave us complimentary water and were happy to answer our questions about the area. We had a great experience and will definitely return the next time we’re visiting Chicago!"

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"NO breakfast available"

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 20 - Oct 21

Total with taxes and fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 14 - Oct 15

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$89 nightly

$99 total

Oct 8 - Oct 9

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

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$115 nightly

$135 total

Nov 2 - Nov 3

Total with taxes and fees

7.8/10 Good! (2,875 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

9.4/10 Exceptional! (2,390 reviews)

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. SureStay Plus Hotel by Best Western Chicago Lombard

8. Best Western Grant Park Hotel

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

10. Congress Plaza Hotel

11. Travelodge by Wyndham Downtown Chicago

12. Homewood Suites by Hilton Chicago Downtown South Loop

13. Hampton Inn Chicago-O'Hare International Airport

14. Hilton Garden Inn Chicago Downtown South Loop

15. Hotel 505 River North

16. Hyatt House Chicago/West Loop-Fulton Market

17. Hotel Saint Clair- Magnificent Mile

18. The Emily Hotel

19. Palmer House a Hilton Hotel

20. Hyatt Place Chicago/Downtown - The Loop

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

River Hotel

Congress Plaza Hotel

The Chicago Hotel Collection - Magnificent Mile

Club Quarters Hotel, Central Loop, Chicago

Sports Illustrated Resorts Chicago

The Godfrey Hotel Chicago

Hotel Saint Clair- Magnificent Mile

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

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