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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Southwest Side

Pet friendly

Spa

Pool

Hot tub

Apart hotel

Family friendly

Waterpark

Condo

Apartment

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 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.

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 $191

CA $238 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.

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 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.

2. Carlton Inn Midway

Archer Heights

stephen T

CA $151

CA $178 total

includes taxes & fees

Oct 20 - Oct 21

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

CA $119

CA $139 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 $173

CA $192 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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.

5. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

CA $173

CA $206 total

includes taxes & fees

Nov 9 - Nov 10

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

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.

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

6. Best Western Grant Park Hotel

Downtown Chicago

Colin

CA $151

CA $180 total

includes taxes & fees

Nov 10 - Nov 11

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 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.

7. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

CA $203

CA $242 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 modern living room with a large window overlooking a body of water, a tripod, and a sofa.

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

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

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

Downtown Chicago

Shanequa

CA $269

CA $369 total

includes taxes & fees

Nov 12 - Nov 13

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

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

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

A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

9. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

CA $243

CA $289 total

includes taxes & fees

Nov 3 - Nov 4

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.

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

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

10. Hilton Chicago

Downtown Chicago

Anna

CA $239

CA $326 total

includes taxes & fees

Nov 13 - Nov 14

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.

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

11. Congress Plaza Hotel

Downtown Chicago

Ashya

CA $148

CA $176 total

includes taxes & fees

Nov 10 - Nov 11

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 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.

12. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

CA $150

CA $179 total

includes taxes & fees

Nov 11 - Nov 12

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.

13. Hotel 505 River North

Downtown Chicago

Jordan

CA $234

CA $323 total

includes taxes & fees

Nov 17 - Nov 18

A modern bathroom with a glass shower enclosure, a toilet, a sink with a mirror, and a towel rack.

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

A modern lobby with a reception desk, seating area, staircase, and decorative lighting.

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

14. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Erin

CA $186

CA $221 total

includes taxes & fees

Nov 1 - Nov 2

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.

15. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Chriselda

CA $227

CA $270 total

includes taxes & fees

Nov 1 - Nov 2

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 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 snack and beverage kiosk with various snacks and drinks.

16. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Shonnette

CA $137

CA $152 total

includes taxes & fees

Oct 26 - Oct 27

A high-rise hotel with a prominent curved glass facade, multiple floors, and a visible "EMBASSY" sign.

A conference room with a long table, chairs, a projector screen, and a carpeted floor.

A modern hotel lobby with a seating area, a reception desk, and artwork on the walls.

A hotel room with a bed, a TV, a window with curtains, and a view of tall buildings.

17. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

jaimie

CA $207

CA $287 total

includes taxes & fees

Nov 1 - Nov 2

A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.

A modern office setup with two monitors, a keyboard, and leather chairs.

A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.

18. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Downtown Chicago

Brock

CA $272

CA $323 total

includes taxes & fees

Oct 30 - Oct 31

A rooftop terrace with lounge chairs and tables, offering a city skyline view.

A modern office space with two desks, each with a computer monitor, a printer, and a lamp. There is an exit sign on the ceiling.

A modern bar area with a stainless steel bar counter, multiple stools, a refrigerated display, and a large window offering a view of the city.

A hotel room with a large bed, two armchairs, a wooden dresser, a desk with a chair, a flat-screen TV, and framed pictures on the wall.

19. Best Western River North Hotel

Downtown Chicago

Jordan

CA $167

CA $199 total

includes taxes & fees

Nov 9 - Nov 10

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

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

20. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

CA $276

CA $328 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

The Wade

8/10 Good

"Convenient location and loved the room."

Fairmont Chicago at Millennium Park

10/10 Excellent

"Good location"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"The room was very clean and front desk lady was very helpful"

Sports Illustrated Resorts Chicago

10/10 Excellent

"I have nothing but great things to say about this stay. From the moment I walked in I felt welcomed. The staff made it a point to try to get me to my room as quickly as possible as they saw I was there for a marathon. The gym was great and they had a recovery lounge and pasta buffet during the weekend. Very intentional. I was traveling alone so the room / size was perfect for me."

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"Room 304 was just fine. The view from the window was really poor and unpleasant. The bathroom small and a bit run down. The hotel entry, reception area and the bars and restaurants were beautiful, elegant and sophisticated."

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Had a great night in a great room!"

Congress Plaza Hotel

10/10 Excellent

"Rooms were nice"

The Godfrey Hotel Chicago

10/10 Excellent

"Clean ,good staff , bathroom could have been cleaner hair from previous stay was everywhere"

Hyatt Regency Chicago

10/10 Excellent

"Had a wonderful weekend at the Hyatt Regency Chicago. Great location, service and very clean and comfortable room."

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

Oct 26 - Oct 27

includes taxes & fees

6.8/10 (2,346 reviews)

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

CA $114

CA $128 total

Oct 25 - Oct 26

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $137

CA $152 total

Oct 26 - Oct 27

includes taxes & fees

9/10 Wonderful! (3,077 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $150

CA $179 total

Nov 11 - Nov 12

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

CA $155

CA $184 total

Nov 1 - Nov 2

includes taxes & fees

8/10 Very good! (1,683 reviews)

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

CA $175

CA $202 total

Oct 25 - Oct 26

includes taxes & fees

Hotels in Southwest Side with star rating

Explore a world of travel with Expedia

Things to do in Chicago

Book Hotels in Southwest Side on Expedia.com

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 Garden Inn Chicago Downtown South Loop

6. Best Western Grant Park Hotel

7. Homewood Suites by Hilton Chicago Downtown South Loop

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

9. Hilton Vacation Club Hotel Blake Chicago

10. Hilton Chicago

11. Congress Plaza Hotel

12. Travelodge by Wyndham Downtown Chicago

13. Hotel 505 River North

14. Hampton Inn & Suites Chicago Downtown

15. Crowne Plaza Chicago West Loop by IHG

16. SureStay Plus Hotel by Best Western Chicago Lombard

17. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

18. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

19. Best Western River North Hotel

20. Hyatt House Chicago/West Loop-Fulton Market

Stay near popular Southwest Side attractions

Marquette Park

Union Stock Yard Gate

S.S. Peter and Paul Church

Balzekas Museum of Lithuanian Culture

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Wade

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection - Magnificent Mile

Sports Illustrated Resorts Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Hotel Saint Clair- Magnificent Mile

Congress Plaza Hotel

The Godfrey Hotel 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

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

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