Top 10 Hotels in Southwest Side (from $90) 2026 - Competitive Prices

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Our top choices for Southwest Side hotels

A modern bar area with a curved counter, multiple stools, and pendant lighting.

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.

A modern bar area with a bar counter, seating, and large windows offering a view of the street.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Laura

$121 nightly

$140 total

Nov 24 - Nov 25

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 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.

2. Carlton Inn Midway

Archer Heights

stephen T

$107 nightly

$126 total

Oct 27 - Oct 28

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

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 27 - Oct 28

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 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.

4. Carleton of Oak Park

Oak Park

Brad

$109 nightly

$121 total

Oct 28 - Oct 29

Total with taxes and fees

A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

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

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

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

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

Downtown Chicago

Angela

$160 nightly

$190 total

Nov 23 - Nov 24

Total with taxes and fees

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

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

A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.

A modern conference room with a wooden table, white chairs, a potted plant, and a large window with decorative plants.

6. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

tahira

$160 nightly

$191 total

Nov 15 - Nov 16

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 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.

7. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

$97 nightly

$115 total

Nov 23 - Nov 24

Total with taxes and fees

A modern hotel lobby with seating areas, a reception desk, and an elevator.

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.

8. Best Western Grant Park Hotel

Downtown Chicago

Colin

$98 nightly

$117 total

Nov 23 - Nov 24

Total with taxes and fees

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

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

Cynthia

$110 nightly

$130 total

Nov 23 - Nov 24

Total with taxes and fees

A modern indoor pool area with clear glass walls, lounge chairs, 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.

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.

10. Hotel 505 River North

Downtown Chicago

Miya

$164 nightly

$195 total

Nov 24 - Nov 25

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

A modern lounge area with seating, a bar, and large windows offering views.

11. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

$143 nightly

$170 total

Nov 23 - Nov 24

Total with taxes and fees

A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.

A spacious lobby with a patterned carpet, seating area, and a fireplace.

A spacious hotel lobby with a large seating area, a flat-screen TV, and a view of the ocean.

A multi-story building with a prominent entrance featuring a large archway and a sign.

12. Hilton Chicago

Downtown Chicago

Anna

$162 nightly

$190 total

Nov 26 - Nov 27

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

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

13. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

$118 nightly

$140 total

Nov 23 - Nov 24

Total with taxes and fees

A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

A hotel reception area with a wall sign reading 'welcome to Hampton' and a wall-mounted sign indicating a treats section.

14. Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

Michael

$114 nightly

$136 total

Nov 23 - Nov 24

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.

15. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Khadija

$89 nightly

$99 total

Oct 28 - Oct 29

Total with taxes and fees

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

A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

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

A hotel room with a sofa, a small table, a bed, and a view of the city through a window.

16. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Chriselda

$134 nightly

$159 total

Nov 24 - Nov 25

Total with taxes and fees

A cityscape at dusk with illuminated skyscrapers and a river.

An outdoor dining area with tables and umbrellas, overlooking a river with a bridge and high-rise buildings in the background.

A spacious lobby with a high ceiling, modern seating, and a central bar area.

A spacious lobby with a central bar area, seating, and a large window offering a city view.

17. Holiday Inn Chicago Dwtn - The Mart by IHG

Downtown Chicago

Pamela

$147 nightly

$175 total

Nov 22 - Nov 23

Total with taxes and fees

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.

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

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

18. Congress Plaza Hotel

Downtown Chicago

Ashya

$104 nightly

$124 total

Nov 22 - Nov 23

Total with taxes and fees

A rooftop terrace with outdoor seating, a pergola, and a view of surrounding high-rise buildings.

A modern hotel room with a sofa, a small table, a kitchen area with wine bottles, and large windows offering a view of the building's exterior.

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

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

Downtown Chicago

Danielle

$136 nightly

$162 total

Nov 22 - Nov 23

Total with taxes and fees

A multi-story building with a prominent curved glass facade, surrounded by other high-rise buildings.

A multi-level hotel lobby with a central food service area, multiple dining tables, and a modern architectural design.

A hotel reception area with a modern design, featuring a black reception desk, a 'Concierge' sign, and a 'Stairs' sign indicating the direction to the street level.

A hotel room with two beds, a large window with a city view, a wooden wardrobe, and a bedside table with a lamp.

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

jaimie

$134 nightly

$178 total

Nov 25 - Nov 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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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

Congress Plaza Hotel

10/10 Excellent

"What a charming and beautiful hotel. The building needs some updating, however, it's a glorious and magnificent hotel."

River Hotel

8/10 Good

"Excellent location. Check in with tablets is silly and irritating while Guest Services Clerk stands at the desk."

Hilton Chicago

8/10 Good

"Everyone so nice but long lines to check in."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"A wonderful place with a prime location in an exclusive, central neighborhood. The hotel is beautiful and spotless, the food is delicious, and the bed is super comfortable! You can tell how much they prioritize cleanliness throughout the entire stay."

The Royal Sonesta Chicago Downtown

8/10 Good

"First the good: the location is great, right on the river and easily walkable to the Loop of the Magnificent Mile, etc. I arrived early and asked to check my bag, but my room was ready, which was nice. Somehow I got a fabulous upgrade to a comfortable spacious corner room on the 38th floor with the most spectacular views (views plural). When I returned later to rest before dinner, I couldn’t stop looking out the windows—what a show at sunset! The bed was very comfortable, although really really high off the ground. Everything seemed clean. Now the not-so-good: lighting was very sparse in the room—half the room had no lighting at all. No place to charge devices—hello, this is 2026. I had a little trouble with the temperature and there was no way to call downstairs—everything has to be handled in the app. So do stay here, but bring a charging station to plug into the wall—which is far from the bed."

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Very nice affordable place to stay !!!"

Freehand Chicago

8/10 Good

"Good value"

Fairmont Chicago at Millennium Park

10/10 Excellent

"I really enjoyed my stay here! One of the first things I noticed was how clean and well-kept everything was, which made me feel comfortable right away. The staff was amazing, always friendly, welcoming, and willing to help with anything I needed. I also really appreciated how convenient the location was. It made getting around so much easier. It's always nice to stay somewhere that feels comfortable and where you're treated well. I had a great experience overall and would definitely stay here again. Highly recommend!"

More cheap stays in Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$81 nightly

$90 total

Nov 2 - Nov 3

Total with taxes and fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

$89 nightly

$99 total

Oct 28 - Oct 29

Total with taxes and fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

$101 nightly

$119 total

Nov 16 - Nov 17

Total with taxes and fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$106 nightly

$124 total

Nov 12 - Nov 13

Total with taxes and fees

7.8/10 Good! (2,947 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$118 nightly

$140 total

Nov 23 - Nov 24

Total with taxes and fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

$124 nightly

$143 total

Nov 1 - Nov 2

Total with taxes and fees

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 $90

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. Sable at Navy Pier Chicago, Curio Collection by Hilton

6. Hilton Vacation Club Hotel Blake Chicago

7. Hilton Garden Inn Chicago Downtown South Loop

8. Best Western Grant Park Hotel

9. Homewood Suites by Hilton Chicago Downtown South Loop

10. Hotel 505 River North

11. Hyatt House Chicago/West Loop-Fulton Market

12. Hilton Chicago

13. Hyatt Place Chicago/Downtown - The Loop

14. Hampton Inn Majestic Chicago Theatre District

15. SureStay Plus Hotel by Best Western Chicago Lombard

16. Crowne Plaza Chicago West Loop by IHG

17. Holiday Inn Chicago Dwtn - The Mart by IHG

18. Congress Plaza Hotel

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

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Stay near popular Southwest Side attractions

Marquette Park

Union Stock Yard Gate

Balzekas Museum of Lithuanian Culture

S.S. Peter and Paul Church

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

Congress Plaza Hotel

River Hotel

Hilton Chicago

The Chicago Hotel Collection Ambassador Gold Coast

The Royal Sonesta Chicago Downtown

Hotel Saint Clair- Magnificent Mile

Freehand Chicago

Fairmont Chicago at Millennium Park

More cheap stays in Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

SureStay Plus Hotel by Best Western Chicago Lombard

Sleep Inn Midway Airport Bedford Park

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

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