Top 10 Hotels in Southwest Side (from $59) 2026 - Competitive Prices

An airplane exhibit labeled "Concourse A" in an airport terminal.

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

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Fabian

$162 nightly

$188 total

Sep 27 - Sep 28

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 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.

A reception area with a wooden reception desk, a sofa, and a coffee table.

2. Carlton Inn Midway

Archer Heights

Icaro

$118 nightly

$138 total

Oct 12 - Oct 13

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

3. Rainbow Motel

Garfield Ridge

Noel

$77 nightly

$90 total

Sep 17 - Sep 18

Total with taxes and fees

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

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.

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

4. Congress Plaza Hotel

Downtown Chicago

Manuel

$164 nightly

$195 total

Oct 7 - Oct 8

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 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.

5. Best Western Grant Park Hotel

Downtown Chicago

Diego

$179 nightly

$213 total

Sep 29 - Sep 30

Total with taxes and fees

A spacious lobby with a central coffee table, sofas, and a large mirror.

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

6. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Laura

$188 nightly

$223 total

Sep 29 - Sep 30

Total with taxes and fees

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

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.

7. Hilton Chicago

Downtown Chicago

Lori

$260 nightly

$305 total

Sep 25 - Sep 26

Total with taxes and fees

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

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

8. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Matthew

$155 nightly

$184 total

Sep 29 - Sep 30

Total with taxes and fees

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

A man in a suit sitting by a window with a vase of red flowers.

A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.

A conference room with a long table, chairs, and a vase.

9. River Hotel

Downtown Chicago

steve

$152 nightly

$181 total

Sep 27 - Sep 28

Total with taxes and fees

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

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.

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

10. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Phillip

$164 nightly

$195 total

Sep 20 - Sep 21

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 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 hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

11. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Dhannetta

$219 nightly

$260 total

Sep 29 - Sep 30

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 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.

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

Downtown Chicago

Ashraf

$314 nightly

$373 total

Oct 1 - Oct 2

Total with taxes and fees

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

A cozy seating area with a round table and two chairs, a brick wall, 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 lobby with two brown leather chairs, a marble table, and a large potted plant.

13. LIVN - West Loop Chicago

Downtown Chicago

Tomas

$205 nightly

$241 total

Sep 20 - Sep 21

Total with taxes and fees

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

A modern bar area with a bar counter, multiple stools, and a chandelier.

A man and a woman walking down a marble staircase in a hotel lobby with a chandelier and a sign indicating an exit.

A cityscape with modern skyscrapers, a waterfront, and a winter setting.

14. Silversmith Hotel Chicago Downtown

Downtown Chicago

Kun

$225 nightly

$267 total

Sep 27 - Sep 28

Total with taxes and fees

A grand lobby with a central bar, high ceilings, and classical architecture.

A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.

A modern living room with a round dining table, bar stools, a purple armchair, and a sofa with cushions.

A modern living room with a sofa set, ottoman, and armchairs.

15. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Scott

$159 nightly

$189 total

Sep 27 - Sep 28

Total with taxes and fees

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

A modern high-rise hotel with multiple floors, large windows, and a well-lit entrance area.

A modern indoor swimming pool with blue seating and a view of the city through large windows.

A modern hotel room with a bed, a sofa, a coffee table with flowers, a TV, and a large window with a city view.

16. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Jerry

$179 nightly

$213 total

Sep 20 - Sep 21

Total with taxes and fees

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.

A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

17. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

$197 nightly

$235 total

Oct 1 - Oct 2

Total with taxes and fees

A Holiday Inn & Suites building with multiple parking spaces and a modern architectural design.

A modern lobby with a central seating area, a reception desk, and elevators.

A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden table, set against a modern room with a white sofa and a wooden accent wall.

A hotel room with a bed, desk, chair, two small tables, a sofa, and a large window with a city view.

18. Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

Jennifer

$196 nightly

$233 total

Sep 20 - Sep 21

Total with taxes and fees

A modern building with a colorful facade and a red circular seating area.

A modern high-rise building with a glass facade, surrounded by other tall buildings.

A modern hotel room with a large window offering a city view, a contemporary light fixture, and a clean, minimalist design.

A modern interior with wooden shelves, colorful chairs, and hanging plants.

19. citizenM Chicago Downtown

Downtown Chicago

Germaine

$193 nightly

$229 total

Sep 20 - Sep 21

Total with taxes and fees

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

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

A person sitting on a couch with a laptop, reading a book, in a room with a large window and a framed picture on the wall.

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

20. Central Loop Hotel

Downtown Chicago

Yiyang

$169 nightly

$201 total

Sep 27 - Sep 28

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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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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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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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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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 Royal Sonesta Chicago Downtown

10/10 Excellent

"Everything was outstanding"

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Nice place to stay"

Hilton Chicago

10/10 Excellent

"My stay at the Chicago Hilton was truly exceptional. From the moment I arrived, I was impressed by the beautiful and elegant surroundings, outstanding amenities, and impeccable service. The staff were gracious, attentive, and professional, making the entire experience feel warm and welcoming. The hotel itself is absolutely gorgeous, with amenities that exceeded my expectations. I look forward to staying here again and would highly recommend the Chicago Hilton to anyone seeking a memorable and luxurious experience in Chicago."

Travelodge by Wyndham Downtown Chicago

10/10 Excellent

"TV didn't work"

Fairmont Chicago at Millennium Park

10/10 Excellent

"We had a wonderful two-night stay at Fairmont Chicago last weekend. We were so happy and pleasantly surprised when the hotel upgraded us to a beautiful suite. The suite was spacious, comfortable, and very nice, which made our stay even more special. We also really enjoyed the Gold Lounge. It was beautiful, comfortable, and offered a wonderful place to relax and enjoy food and drinks. The service was excellent, and everyone was friendly and welcoming. We truly enjoyed our stay and were very happy with our experience at Fairmont Chicago. We would definitely love to stay here again!"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Property was clean in perfect location. Close to restaurants, shopping, and the beach"

Congress Plaza Hotel

8/10 Good

"My stay was great. But the hallway was off putting."

Warwick Allerton - Chicago

10/10 Excellent

"It was our first time in Chicago, and we would definitely stay here again. The hotel is clean, quiet, and so pretty. (with an art deco vibe) It’s also located in a great area, very easily walkable to most shops/attractions/etc that were already on our list. The staff was so friendly. I wish I got the name of the lovely lady who was so generous to my friends and I. Overall such a nice comfy place to stay at!"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"I really liked the fact they had water stations with bottles you could fill up"

More cheap stays in Southwest Side

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL

$52 nightly

$59 total

Oct 12 - Oct 13

Total with taxes and fees

7.8/10 Good! (2,005 reviews)

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

$57 nightly

$64 total

Sep 28 - Sep 29

Total with taxes and fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

$118 nightly

$139 total

Oct 4 - Oct 5

Total with taxes and fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$155 nightly

$184 total

Sep 29 - Sep 30

Total with taxes and fees

7.6/10 Good! (2,829 reviews)

Holiday Inn Express Chicago - Magnificent Mile by IHG

640 N Wabash Ave Chicago IL

$199 nightly

$237 total

Sep 20 - Sep 21

Total with taxes and fees

8.4/10 Very Good! (1,329 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$203 nightly

$242 total

Sep 20 - Sep 21

Total with taxes and fees

8/10 Very Good! (1,596 reviews)

Hotels in Southwest Side with star-rating

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Find hotels in Southwest Side, IL from $59

Go beyond your typical stay in Southwest Side

Check prices for these dates

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Star rating

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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. Congress Plaza Hotel

5. Best Western Grant Park Hotel

6. The Chicago Hotel Collection Ambassador Gold Coast

7. Hilton Chicago

8. Travelodge by Wyndham Downtown Chicago

9. River Hotel

10. Crowne Plaza Chicago West Loop by IHG

11. Hilton Garden Inn Chicago Downtown South Loop

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

13. LIVN - West Loop Chicago

14. Silversmith Hotel Chicago Downtown

15. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

16. Aloft by Marriott Chicago Mag Mile

17. Hilton Chicago/Magnificent Mile Suites

18. Holiday Inn & Suites Chicago - Downtown by IHG

19. citizenM Chicago Downtown

20. Central Loop Hotel

Stay near popular Southwest Side attractions

Marquette Park

S.S. Peter and Paul Church

Balzekas Museum of Lithuanian Culture

Ephraim Bajar Cultural Center

Union Stock Yard Gate

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

The Royal Sonesta Chicago Downtown

Hotel Saint Clair- Magnificent Mile

Hilton Chicago

Travelodge by Wyndham Downtown Chicago

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection Ambassador Gold Coast

Congress Plaza Hotel

Warwick Allerton - Chicago

Club Quarters Hotel, Central Loop, Chicago

More cheap stays in Southwest Side

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Naperville, IL

Sleep Inn Midway Airport Bedford Park

Travelodge by Wyndham Downtown Chicago

Holiday Inn Express Chicago - Magnificent Mile by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Southwest Side with star-rating

Explore a world of travel with Expedia