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

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Southwest Side

Pet friendly

Spa

Hot tub

Pool

Apart hotel

Family friendly

Apartment

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

$141 nightly

$164 total

Nov 8 - Nov 9

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

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

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

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

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

3. Rainbow Motel

Garfield Ridge

Jerry

$93 nightly

$109 total

Oct 12 - Oct 13

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 12 - Oct 13

Total with taxes and fees

A hallway with a patterned carpet, a chandelier, and a neon sign.

A hotel reception area with a black counter, a chandelier, a television, and a floral wallpaper.

A spacious living room with a grand piano, a glass coffee table, a sofa, and a couch.

5. The Tremont Chicago Hotel

Downtown Chicago

"The room smelled of paint and wallpaper glue so strongly it made my nose run. Additionally, the controls for the wall were ancient and hard to use in the dark. There were open holes in the wall with cords running in them, grimy bathroom corners, and cracked door frames for the bathroom. The entrance seems nice, until you get to the rooms. The front desk wasn’t staffed when I tried to check out in the morning. After waiting for 5 minutes, I dropped my room key and left."

Seth

$107 nightly

$128 total

Oct 25 - Oct 26

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

A restaurant with booths and tables, a television on the wall, and a view of the street outside.

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

6. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

$181 nightly

$216 total

Oct 29 - Oct 30

Total with taxes and fees

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

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.

7. 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 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.

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

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

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.

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

9. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

$161 nightly

$192 total

Oct 25 - Oct 26

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 snack and beverage kiosk with various snacks and drinks.

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.

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.

10. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

$97 nightly

$107 total

Oct 21 - Oct 22

Total with taxes and fees

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

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.

A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.

11. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$115 nightly

$135 total

Nov 2 - Nov 3

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

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

12. Congress Plaza Hotel

Downtown Chicago

Katimah

$122 nightly

$144 total

Nov 5 - Nov 6

Total with taxes and fees

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

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.

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

13. 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.

14. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jennifer

$125 nightly

$144 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

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.

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

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

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

16. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$187 nightly

$222 total

Oct 25 - Oct 26

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 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.

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.

17. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Adhba

$146 nightly

$171 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 modern lobby with a sofa, coffee table, and potted plants.

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

A window with a view of a cityscape, a wooden desk with a radio, and a small window ledge.

18. The Emily Hotel

Downtown Chicago

Leslie

$291 nightly

$346 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

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

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.

19. Hotel 505 River North

Downtown Chicago

Giana

$216 nightly

$257 total

Nov 8 - Nov 9

Total with taxes and fees

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

A hotel room with a large bed, a desk with a computer, a TV, and a seating area with a chair and ottoman.

A spacious lobby with a seating area, a reception desk, and a large screen.

A spacious lobby with high wooden pillars, a seating area with sofas and a bench, a fire feature, and a modern design.

20. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Chriselda

$179 nightly

$213 total

Nov 8 - Nov 9

Total with taxes and fees

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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

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.

See properties

Union Stock Yard Gate

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

See properties

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.

See properties

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.

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

Hilton Chicago

10/10 Excellent

"Our stay at the Hilton Chicago was excellent.The rooms were clean,staff very professional,and food was excellent."

The Godfrey Hotel Chicago

8/10 Good

"It was a great stay except for the fact that the toilet in the room made a lot of noise when it wasn’t being used - every 45 min or so it would make a loud noise"

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The hotel is in a nice neighborhood and the room was clean. The bed and toilet were both very low to the ground, and there were very few electrical outlets, but otherwise it was a pleasant stay."

Hilton Chicago O'Hare Airport

10/10 Excellent

"Excellent staff and friendly helpful. Excellent stay and will stay again."

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Staff was amazing!! They were all so kind and attentive! I enjoyed my stay so much and I’m looking on planning another trip just to stay at this hotel!"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"CQ is a reliable brand as this property demonstrated. I was particularly pleased with the size of the room and fitness facility. Best CQ I have stayed at and would return. Two quibbles: No desk lamp, therefore a dark work area and no hand soap (use body gel? I bring my own). Housekeeping excellent."

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 15 - Oct 16

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$97 nightly

$107 total

Oct 21 - Oct 22

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! (1,656 reviews)

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! (2,885 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

9.4/10 Exceptional! (2,394 reviews)

Hotels in Southwest Side with star-rating

Explore a world of travel with Expedia

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. The Tremont Chicago Hotel

6. Hilton Vacation Club Hotel Blake Chicago

7. Hilton Chicago

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

9. Best Western Grant Park Hotel

10. SureStay Plus Hotel by Best Western Chicago Lombard

11. Travelodge by Wyndham Downtown Chicago

12. Congress Plaza Hotel

13. Homewood Suites by Hilton Chicago Downtown South Loop

14. Hampton Inn Chicago-O'Hare International Airport

15. Hyatt House Chicago/West Loop-Fulton Market

16. Hilton Garden Inn Chicago Downtown South Loop

17. Hotel Saint Clair- Magnificent Mile

18. The Emily Hotel

19. Hotel 505 River North

20. Crowne Plaza Chicago West Loop by IHG

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

Hilton Chicago

The Godfrey Hotel Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago O'Hare Airport

The Royal Sonesta Chicago Downtown

Club Quarters Hotel, Central Loop, 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

Go further with the Expedia app