Top 10 Hotels in Southwest Side (from $60) 2026 - Competitive Prices

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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 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 modern lobby with a vending machine, a statue, and an exit sign.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Diane

$141 nightly

$164 total

Sep 9 - Sep 10

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

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 modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.

2. Carlton Inn Midway

Archer Heights

Icaro

$104 nightly

$122 total

Sep 13 - Sep 14

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 compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

A small bathroom with a white sink, a mirror, and a window with an air conditioning unit.

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

Oct 6 - Oct 7

Total with taxes and fees

A hotel entrance with a classic facade, an American flag, and a sign for Hotel Blake Chicago.

A hotel entrance with a marquee and string lights above the entrance.

A hotel entrance with a marquee, American flag, and a person standing in front.

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Melanie

$199 nightly

$237 total

Sep 7 - Sep 8

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 view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

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

Ashraf

$210 nightly

$250 total

Sep 8 - Sep 9

Total with taxes and fees

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

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

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

A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.

6. LIVN - West Loop Chicago

Downtown Chicago

Tomas

$156 nightly

$184 total

Sep 7 - Sep 8

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.

7. Congress Plaza Hotel

Downtown Chicago

Manuel

$106 nightly

$126 total

Sep 8 - Sep 9

Total with taxes and fees

A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

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

A modern kitchen area with a long counter, various food items, and a coffee machine.

A modern kitchen with a built-in refrigerator, a coffee maker, and a flat-screen TV on the countertop.

8. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Downtown Chicago

Marissa

$129 nightly

$153 total

Sep 7 - Sep 8

Total with taxes and fees

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

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.

A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.

9. Best Western Grant Park Hotel

Downtown Chicago

Diego

$152 nightly

$181 total

Sep 10 - Sep 11

Total with taxes and fees

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

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

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

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

10. Hilton Chicago

Downtown Chicago

Lori

$224 nightly

$266 total

Sep 7 - Sep 8

Total with taxes and fees

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

A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.

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

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

11. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Laura

$143 nightly

$170 total

Sep 7 - Sep 8

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

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

12. River Hotel

Downtown Chicago

Austin

$161 nightly

$192 total

Sep 8 - Sep 9

Total with taxes and fees

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

A gym with multiple treadmills aligned in rows, a cityscape mural on the wall, and a view of the water outside.

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

The exterior of the Hyatt Centric The Loop hotel with a prominent American flag, a classic facade, and a glass entrance.

13. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

$212 nightly

$252 total

Sep 7 - Sep 8

Total with taxes and fees

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

A bar with a circular liquor display, seating with stools, and a city view through large windows.

A cityscape with modern high-rise buildings, a river, and a boat.

A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.

14. Hyatt Regency Chicago

Downtown Chicago

Steve

$274 nightly

$326 total

Sep 7 - Sep 8

Total with taxes and fees

A modern hotel with a colorful awning and a glass facade.

A bakery display with various baked goods and a coffee machine.

A modern lobby with a reception desk, seating area, and a large illuminated number '5' on the wall.

A hotel room with a wooden wardrobe, a minibar with coffee cups and a bottle, a safe, and a towel rack with a hanging bag.

15. Aloft by Marriott Chicago Downtown River North

Downtown Chicago

Michelle

$180 nightly

$214 total

Sep 7 - Sep 8

Total with taxes and fees

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

A bar area with a marble countertop, bar stools, and a variety of bottles.

A modern hotel lobby with a central seating area, a reception desk, and a decorative wall with a unique design.

A spacious lobby with a marble floor, a reception desk, and a glass partition.

16. Hotel Riu Plaza Chicago

Downtown Chicago

Donna

$170 nightly

$202 total

Sep 7 - Sep 8

Total with taxes and fees

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

A restaurant with outdoor seating, covered by umbrellas, and decorated with hanging planters.

A modern living room with a sofa, chairs, 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.

17. Le Méridien Essex Chicago

Downtown Chicago

amanda

$164 nightly

$195 total

Sep 7 - Sep 8

Total with taxes and fees

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 bar with a brick archway, wooden bar counter, and stools.

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

18. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Jacqueline

$116 nightly

$138 total

Sep 8 - Sep 9

Total with taxes and fees

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

A modern bar area with a checkered floor, wooden ceiling, and various bar equipment.

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

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

19. citizenM Chicago Downtown

Downtown Chicago

lakadria

$174 nightly

$207 total

Sep 7 - Sep 8

Total with taxes and fees

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

A reception area with a modern design, featuring a large window, a reception desk, and artwork on the wall.

A bar area with a granite countertop, bar stools, and a variety of bottles and glasses.

20. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

Jyothi Swaroop

$165 nightly

$196 total

Sep 7 - Sep 8

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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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 acclaimed theater 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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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

"The hotel is in a great location. All major bus and train routes are within two blocks. Rooms are good, area is safe and I would stay again."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Such a beautiful hotel. I loved that it has some history in it. Staff were very kind, friendly and helpful. The rooms were also very clean. Would definitely recommend and will definitely be coming back. If they could add some more elevators that would be awesome."

Hyatt Regency Chicago

10/10 Excellent

"Amazing place to stay. Rooms were very well maintained, staff was friendly, and room was always cleaned on time. Didn't get a chance to get breakfast, but I did eat dinner at Stentons, and I can say it was lovely. Hotel is within walking distance to everything you could possibly dream of. I highly recommend staying here. I will definitely be back to stay. 5 stars all around."

Hotel Saint Clair- Magnificent Mile

8/10 Good

"Both guys at the front desk were very friendly and welcoming. I really enjoyed the historic vibe of the hotel, but the room itself was a little smaller than I expected. I also didn’t like that the iron and ironing board were located in the hallway on each floor instead of inside the room. The bed wasn’t as comfortable as I’m used to at a 4-star hotel, and the room could use a little TLC and a few upgrades. I stayed in room 1007, and although I love being on a higher floor, I would probably choose a different room next time. Overall, I enjoyed my stay and would definitely stay here again because I loved the historic charm of the hotel."

Travelodge by Wyndham Downtown Chicago

8/10 Good

"Room was okay. You get what you pay for nothing special"

Kasa Magnificent Mile Chicago

10/10 Excellent

"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"

More cheap stays in Southwest Side

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL

$53 nightly

$60 total

Oct 1 - Oct 2

Total with taxes and fees

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

$57 nightly

$64 total

Sep 20 - Sep 21

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

$133 nightly

$156 total

Sep 8 - Sep 9

Total with taxes and fees

7.6/10 Good! (2,831 reviews)

Holiday Inn Express Chicago - Magnificent Mile by IHG

640 N Wabash Ave Chicago IL

$154 nightly

$183 total

Sep 7 - Sep 8

Total with taxes and fees

8.4/10 Very Good! (1,315 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$164 nightly

$195 total

Sep 7 - Sep 8

Total with taxes and fees

8/10 Very Good! (1,576 reviews)

Hotels in Southwest Side with star-rating

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Lodging

Find hotels in Southwest Side, IL from $60

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. Hilton Vacation Club Hotel Blake Chicago

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

6. LIVN - West Loop Chicago

7. Congress Plaza Hotel

8. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

9. Best Western Grant Park Hotel

10. Hilton Chicago

11. The Chicago Hotel Collection Ambassador Gold Coast

12. River Hotel

13. Hyatt Centric The Loop Chicago

14. Hyatt Regency Chicago

15. Aloft by Marriott Chicago Downtown River North

16. Hotel Riu Plaza Chicago

17. Le Méridien Essex Chicago

18. Club Quarters Hotel, Central Loop, Chicago

19. citizenM Chicago Downtown

20. Courtyard by Marriott Chicago Magnificent Mile

Stay near popular Southwest Side attractions

Marquette Park

Balzekas Museum of Lithuanian Culture

S.S. Peter and Paul Church

Union Stock Yard Gate

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

Congress Plaza Hotel

InterContinental Chicago Magnificent Mile by IHG

Hyatt Regency Chicago

Hotel Saint Clair- Magnificent Mile

Travelodge by Wyndham Downtown Chicago

Kasa Magnificent Mile 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

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