Book The Best Hotels in Southwest Side, IL for 2026 from CA $101 - Fully Refundable Options

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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 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.

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

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Paulina

CA $187

CA $234 total

includes taxes & fees

Nov 8 - Nov 9

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 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

stephen T

CA $149

CA $175 total

includes taxes & fees

Oct 13 - Oct 14

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 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.

3. Rainbow Motel

Garfield Ridge

Jerry

CA $100

CA $117 total

includes taxes & fees

Oct 12 - Oct 13

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.

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

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Kelsey

CA $259

CA $308 total

includes taxes & fees

Oct 29 - Oct 30

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

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

5. Carleton of Oak Park

Oak Park

Brad

CA $175

CA $194 total

includes taxes & fees

Oct 12 - Oct 13

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

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

A conference room with a long table, chairs, and a large screen.

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

6. Hilton Chicago

Downtown Chicago

Anna

CA $236

CA $323 total

includes taxes & fees

Oct 30 - Oct 31

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

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

7. Best Western Grant Park Hotel

Downtown Chicago

Shelby Ryann

CA $178

CA $212 total

includes taxes & fees

Nov 9 - Nov 10

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.

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.

8. Hotel 505 River North

Downtown Chicago

Giana

CA $269

CA $366 total

includes taxes & fees

Nov 8 - Nov 9

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.

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

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

9. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jennifer

CA $178

CA $205 total

includes taxes & fees

Nov 1 - Nov 2

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

10. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

CA $171

CA $203 total

includes taxes & fees

Nov 2 - Nov 3

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

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

11. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Corinn

CA $205

CA $243 total

includes taxes & fees

Nov 10 - Nov 11

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.

12. Congress Plaza Hotel

Downtown Chicago

Katimah

CA $157

CA $187 total

includes taxes & fees

Nov 10 - Nov 11

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 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.

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

Downtown Chicago

Shanequa

CA $302

CA $408 total

includes taxes & fees

Nov 9 - Nov 10

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.

14. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

ARLEEN

CA $190

CA $229 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

A snack and beverage kiosk with various snacks and drinks.

15. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

CA $138

CA $153 total

includes taxes & fees

Oct 21 - Oct 22

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.

16. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

CA $181

CA $215 total

includes taxes & fees

Nov 10 - Nov 11

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.

17. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

CA $278

CA $331 total

includes taxes & fees

Nov 1 - Nov 2

A tall, modern hotel with a brick facade and numerous windows.

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

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Anand

CA $164

CA $195 total

includes taxes & fees

Nov 2 - Nov 3

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.

A modern hotel with a corner location, large windows, and a green awning.

A modern hotel room with a kitchen area, a dining table with chairs, a sofa, and a large window with curtains.

19. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Catherine

CA $202

CA $240 total

includes taxes & fees

Nov 1 - Nov 2

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

A formal dining room with a round table set for eight, surrounded by leather chairs, a chandelier, and potted plants.

A grand ballroom with ornate chandeliers, round tables with floral centerpieces, and elegant chairs.

A person overlooking a cityscape from a high vantage point.

20. Palmer House a Hilton Hotel

Downtown Chicago

Christy

CA $271

CA $365 total

includes taxes & fees

Oct 31 - Nov 1

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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.

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

Congress Plaza Hotel

8/10 Good

"The Congress is a historic hotel right at the Southern end of Michigan Avenue. Clearly, it's seen better days. Now, they are restoring it floor by floor. But, the main entry to the hotel is pretty rough. Some of the floors haven't been rehabbed, the bar is possibly the poorest bar in terms of quality of any of the historic hotels I've stayed in during my Chicago trips. The check in process is largely like going to the DMV. There's not a lot of customer service or friendly welcoming banter. No valet parking, there isn't daily maid service, either. The room I had was pretty nice, as it had been on the rehabbed side of the South tower. There was only one working elevator on this tower, so the rides up and down were long and packed. The bed was comfortable, the pillows were fluffy, and the bathroom was really good. The Congress is typically less expensive than the more upgraded spots such as the Blackstone, Hilton, or Palmer House."

Eurostars Magnificent Mile

10/10 Excellent

"Great location, clean rooms, super kind staff."

Hilton Chicago

10/10 Excellent

"I enjoyed the property's elegance and location, with all the sightseeing sites within walking distance of the hotel. I also enjoyed the Irish pub and restaurant in the main lobby."

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Beautiful room, friendly staff."

River Hotel

10/10 Excellent

"Really enjoyed the lounge/coffee bar on 2nd floor"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Great location! Beautiful Hotel! Helpful staff!"

Hilton Chicago O'Hare Airport

8/10 Good

"We appreciated the proximity to the airport and the convenience of staying there since we were just making a connection for a flight the next morning"

Fairmont Chicago at Millennium Park

10/10 Excellent

"Great location. Rooms are very comfortable, clean, and luxurious. Had a great sister's weekend at this location!"

Sports Illustrated Resorts Chicago

10/10 Excellent

"Location is a plus, very close to many dining places and shopping. Love the room, very spacious and comfortable for 2 people but honestly could do with 4. Happy hour and events at the hotel definitely made this stay even better!!"

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

CA $88

CA $101 total

Oct 20 - Oct 21

includes taxes & fees

6.8/10 (2,340 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $115

CA $129 total

Oct 17 - Oct 18

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $138

CA $153 total

Oct 21 - Oct 22

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

CA $156

CA $185 total

Nov 1 - Nov 2

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $171

CA $203 total

Nov 2 - Nov 3

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

CA $178

CA $205 total

Nov 1 - Nov 2

includes taxes & fees

Hotels in Southwest Side with star rating

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Things to do in Chicago

Book Hotels in Southwest Side on Expedia.com

Find hotels in Southwest Side, IL from CA $101

Change your mind

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. Hilton Vacation Club Hotel Blake Chicago

5. Carleton of Oak Park

6. Hilton Chicago

7. Best Western Grant Park Hotel

8. Hotel 505 River North

9. Hampton Inn Chicago-O'Hare International Airport

10. Travelodge by Wyndham Downtown Chicago

11. Homewood Suites by Hilton Chicago Downtown South Loop

12. Congress Plaza Hotel

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

14. Hotel Saint Clair- Magnificent Mile

15. SureStay Plus Hotel by Best Western Chicago Lombard

16. Hilton Garden Inn Chicago Downtown South Loop

17. Hyatt House Chicago/West Loop-Fulton Market

18. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

19. Hampton Inn & Suites Chicago Downtown

20. Palmer House a Hilton Hotel

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

Congress Plaza Hotel

Eurostars Magnificent Mile

Hilton Chicago

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

River Hotel

InterContinental Chicago Magnificent Mile by IHG

Hilton Chicago O'Hare Airport

Fairmont Chicago at Millennium Park

Sports Illustrated Resorts 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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