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

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

A reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.

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

$145 nightly

$168 total

Nov 1 - Nov 2

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 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.

A breakfast bar with coffee makers, a toaster, and a variety of pastries.

2. Carlton Inn Midway

Archer Heights

$107 nightly

$126 total

Oct 18 - Oct 19

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 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.

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

3. Rainbow Motel

Garfield Ridge

Jerry

$93 nightly

$109 total

Oct 16 - Oct 17

Total with taxes and fees

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

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

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

$112 nightly

$124 total

Nov 8 - Nov 9

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

A reception area with a marble counter, decorative Buddha statues, and a wall with a quote.

5. Best Western Grant Park Hotel

Downtown Chicago

Colin

$107 nightly

$127 total

Nov 10 - Nov 11

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

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.

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

Downtown Chicago

Shanequa

$219 nightly

$260 total

Nov 12 - Nov 13

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 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 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.

7. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$127 nightly

$151 total

Nov 9 - Nov 10

Total with taxes and fees

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

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

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

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

8. Hilton Chicago

Downtown Chicago

Anna

$193 nightly

$227 total

Oct 30 - Oct 31

Total with taxes and fees

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.

9. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

$144 nightly

$171 total

Nov 10 - Nov 11

Total with taxes and fees

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

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.

A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

10. Congress Plaza Hotel

Downtown Chicago

Ashya

$106 nightly

$126 total

Nov 11 - Nov 12

Total with taxes and fees

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

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

11. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Mario

$172 nightly

$204 total

Nov 3 - Nov 4

Total with taxes and fees

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

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

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

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

12. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$116 nightly

$136 total

Nov 10 - Nov 11

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 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.

13. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Dimitrina

$97 nightly

$107 total

Oct 22 - Oct 23

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 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.

14. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

$195 nightly

$232 total

Nov 1 - Nov 2

Total with taxes and fees

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

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.

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

15. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Catherine

$133 nightly

$158 total

Nov 1 - Nov 2

Total with taxes and fees

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

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

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

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

16. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

jaimie

$155 nightly

$206 total

Nov 1 - Nov 2

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 modern hotel room with a large window, a desk with a lamp, a sofa, and a chair.

A hotel room with a large bed, a desk with a chair, a sofa, and a TV.

17. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

$195 nightly

$232 total

Nov 1 - Nov 2

Total with taxes and fees

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 modern building with large glass windows and a covered walkway.

18. Palmer House a Hilton Hotel

Downtown Chicago

Christy

$218 nightly

$256 total

Oct 31 - Nov 1

Total with taxes and fees

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

A hotel room with two beds, a desk with a television, a chair, a ceiling fan, and a window with a view of a building.

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.

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

Downtown Chicago

Brock

$194 nightly

$230 total

Oct 30 - Oct 31

Total with taxes and fees

A modern hotel with a glass facade, multiple floors, and a prominent sign.

A modern living room with a large bookshelf, a sofa, a coffee table, and a view of the cityscape.

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

A modern retail space with a central wooden counter, a cityscape mural, and shelves stocked with snacks and beverages.

20. Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

Terri

$229 nightly

$272 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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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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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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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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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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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

Fairmont Chicago at Millennium Park

10/10 Excellent

"clean, perfect for a family trip!"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"That staff were very friendly and accommodating! Would definitely come back!"

Hilton Chicago

10/10 Excellent

"The property was great"

The Godfrey Hotel Chicago

10/10 Excellent

"Very nice option Clean with nice staff Rooms are perfectly adequate and clean Bathroom could do with a small Upgrade but just fine"

Hotel Saint Clair- Magnificent Mile

8/10 Good

"Nice enough room on the small side with tight bathroom. Small lobby. It is what it is. Convenient location. No real complaints"

River Hotel

10/10 Excellent

"We got both an unexpected upgrade & early check in when we arrived! Not only is it in an ideal location, but there are perks like a water bottle filling station on each floor & a free espresso/coffee bar station on 2nd floor. Hotel staff was always responsive to our questions at the desk during our stay."

Eurostars Magnificent Mile

10/10 Excellent

"Very cute and quaint with a wonderful staff. Hotel was also walkable to many restaurants and shops. We will be back!"

Freehand Chicago

10/10 Excellent

"It was comfortable"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"The staff was 10/10."

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 21 - Oct 22

Total with taxes and fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Oct 22 - Oct 23

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$97 nightly

$107 total

Oct 22 - Oct 23

Total with taxes and fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$110 nightly

$130 total

Nov 1 - Nov 2

Total with taxes and fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$116 nightly

$136 total

Nov 10 - Nov 11

Total with taxes and fees

7.8/10 Good! (2,904 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

Hotels in Southwest Side with star-rating

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Things to do in Chicago

Find hotels in Southwest Side, IL from $71

Go beyond your typical stay in Southwest Side

Check prices for these dates

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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. Best Western Grant Park Hotel

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

7. Hilton Garden Inn Chicago Downtown South Loop

8. Hilton Chicago

9. Homewood Suites by Hilton Chicago Downtown South Loop

10. Congress Plaza Hotel

11. Hilton Vacation Club Hotel Blake Chicago

12. Travelodge by Wyndham Downtown Chicago

13. SureStay Plus Hotel by Best Western Chicago Lombard

14. Hyatt House Chicago/West Loop-Fulton Market

15. Hampton Inn & Suites Chicago Downtown

16. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

17. Hyatt Place Chicago/Downtown - The Loop

18. Palmer House a Hilton Hotel

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

20. Hampton Inn Chicago West Loop Fulton Market Area

Stay near popular Southwest Side attractions

Marquette Park

Union Stock Yard Gate

Balzekas Museum of Lithuanian Culture

Ephraim Bajar Cultural Center

S.S. Peter and Paul Church

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago

The Godfrey Hotel Chicago

Hotel Saint Clair- Magnificent Mile

River Hotel

Eurostars Magnificent Mile

Freehand Chicago

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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