Book The Best Hotels in Southwest Side, IL for 2026 from CA $100 - Fully Refundable Options

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Go beyond your typical stay in Southwest Side

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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

Ashima

CA $186

CA $232 total

includes taxes & fees

Oct 28 - Oct 29

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 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.

2. Carlton Inn Midway

Archer Heights

Icaro

CA $148

CA $174 total

includes taxes & fees

Sep 30 - Oct 1

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 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

CA $109

CA $128 total

includes taxes & fees

Oct 20 - Oct 21

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.

4. Carleton of Oak Park

Oak Park

Brad

CA $160

CA $177 total

includes taxes & fees

Sep 30 - Oct 1

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

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.

5. Hilton Chicago

Downtown Chicago

Alan

CA $235

CA $321 total

includes taxes & fees

Oct 30 - Oct 31

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

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

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.

6. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

CA $410

CA $487 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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

7. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

CA $264

CA $314 total

includes taxes & fees

Oct 25 - Oct 26

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 snack and beverage kiosk with various snacks and drinks.

8. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Blessing

CA $133

CA $147 total

includes taxes & fees

Sep 30 - Oct 1

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

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.

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

9. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cecilia

CA $272

CA $324 total

includes taxes & fees

Oct 25 - Oct 26

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.

10. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

karen

CA $198

CA $228 total

includes taxes & fees

Oct 30 - Oct 31

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

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

11. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

CA $210

CA $250 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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.

12. Congress Plaza Hotel

Downtown Chicago

Guadalupe

CA $224

CA $267 total

includes taxes & fees

Oct 25 - Oct 26

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

A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.

A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

A lobby with two brown leather chairs, a marble table, and a large potted plant.

13. LIVN - West Loop Chicago

Downtown Chicago

chidubem

CA $260

CA $306 total

includes taxes & fees

Oct 1 - Oct 2

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.

A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

14. The Wade

Downtown Chicago

Erin

CA $211

CA $251 total

includes taxes & fees

Oct 25 - Oct 26

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.

15. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Peter

CA $212

CA $256 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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.

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

Downtown Chicago

Shanequa

CA $387

CA $509 total

includes taxes & fees

Oct 29 - Oct 30

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

A hotel room with a large window, a bed, and a suitcase.

A modern living room with a fireplace, leather sofas, and a wooden floor.

17. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Julian

CA $178

CA $212 total

includes taxes & fees

Oct 25 - Oct 26

A street view with a row of parked cars, a building with a sign reading "SONDE," and another sign that says "Diamonds On Parade."

A restaurant with outdoor seating and a sign for 'PIZANO'S PIZZA & PASTA'.

A modern kitchen with a dining area featuring two teal chairs, a round table, and a framed artwork on the wall.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a coffee maker. There is a blue sofa and a round coffee table with a striped pattern. A dining area with a table and chairs is visible in the background.

18. LIVN - Millennium Park Downtown Chicago

Downtown Chicago

Rebecca

CA $290

CA $340 total

includes taxes & fees

Oct 1 - Oct 2

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

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.

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

19. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Phillip

CA $268

CA $318 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

20. Le Méridien Essex Chicago

Downtown Chicago

Kayla Rene

CA $350

CA $442 total

includes taxes & fees

Oct 30 - Oct 31

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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

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Great room very roomy just had a couple problems. The water wo"

Congress Plaza Hotel

10/10 Excellent

"What a beautiful unique hotel. Everyone was extremely helpful giving guidance to the many Chicago sites."

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"Bathroom extremely small but room very spacious"

L7 Chicago by LOTTE

10/10 Excellent

"Really enjoyed the stay! They even sent us a microwave to the room upon request. Love the location and the design."

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"The only improvement would be lighting above the desk."

Central Loop Hotel

10/10 Excellent

"I had a wonderful stay at the Central Loop Hotel. The hotel offered the option of a fully automated check-in, which was very convenient, while staff were also readily available and consistently friendly and helpful. My room was clean and quiet and had everything I needed, including a Nespresso machine. After checkout, the hotel stored my bags for several hours so I could spend more time exploring Chicago before my train. The location was excellent…an easy walk from Union Station and very convenient for seeing the city. There is also a very popular restaurant accessible directly through the hotel lobby. I would happily stay here again, particularly when traveling by train. The combination of location, comfort, and helpful staff made for a very easy and enjoyable stay."

Hilton Chicago

10/10 Excellent

"Very good stay the hotel was clean and the bed was comfortable, close to all the good spots as well. I’d stay here again in the future"

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent

"Traveling cross country and stayed at several hotel. This one was on point, from entering the hotel, smelling clean, the staff checking in was great, and the room was clean. I had an awesome stay."

The Wade

10/10 Excellent

"Everything great and everyone e great"

More cheap stays in Southwest Side

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

CA $87

CA $100 total

Sep 30 - Oct 1

includes taxes & fees

6.8/10 (2,357 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $105

CA $117 total

Sep 30 - Oct 1

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $133

CA $147 total

Sep 30 - Oct 1

includes taxes & fees

9/10 Wonderful! (3,039 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

CA $198

CA $228 total

Oct 30 - Oct 31

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $210

CA $250 total

Oct 25 - Oct 26

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

CA $288

CA $342 total

Oct 25 - Oct 26

includes taxes & fees

8/10 Very good! (1,640 reviews)

Hotels in Southwest Side with star rating

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Find hotels in Southwest Side, IL from CA $100

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. Carleton of Oak Park

5. Hilton Chicago

6. Hilton Vacation Club Hotel Blake Chicago

7. Hilton Garden Inn Chicago Downtown South Loop

8. SureStay Plus Hotel by Best Western Chicago Lombard

9. Homewood Suites by Hilton Chicago Downtown South Loop

10. Hampton Inn Chicago-O'Hare International Airport

11. Travelodge by Wyndham Downtown Chicago

12. Congress Plaza Hotel

13. LIVN - West Loop Chicago

14. The Wade

15. Hotel Saint Clair- Magnificent Mile

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

17. Club Quarters Hotel, Central Loop, Chicago

18. LIVN - Millennium Park Downtown Chicago

19. Crowne Plaza Chicago West Loop by IHG

20. Le Méridien Essex Chicago

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

The Chicago Hotel Collection - Magnificent Mile

Congress Plaza Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

L7 Chicago by LOTTE

Club Quarters Hotel, Central Loop, Chicago

Central Loop Hotel

Hilton Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

The Wade

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-O'Hare International Airport

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Southwest Side with star rating

Explore a world of travel with Expedia

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