Top 10 Hotels in Southwest Side (from $64) 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 hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

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 7 - Sep 8

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

2. Carlton Inn Midway

Archer Heights

Rahul Pandit

$119 nightly

$140 total

Sep 3 - Sep 4

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

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.

3. Rainbow Motel

Garfield Ridge

Noel

$81 nightly

$95 total

Sep 12 - Sep 13

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.

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

George

$101 nightly

$120 total

Sep 8 - Sep 9

Total with taxes and fees

A spacious lobby with a patterned carpet, comfortable seating, a fireplace, and large windows.

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

A cityscape with modern high-rise buildings, a train station, and a body of water in the background.

A rooftop lounge with outdoor seating and a view of the city skyline.

5. Hilton Chicago

Downtown Chicago

Konner

$197 nightly

$231 total

Sep 9 - Sep 10

Total with taxes and fees

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

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

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

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

6. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Laura

$122 nightly

$144 total

Sep 8 - Sep 9

Total with taxes and fees

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.

7. Best Western Grant Park Hotel

Downtown Chicago

Diego

$143 nightly

$170 total

Sep 7 - Sep 8

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

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

8. LIVN - West Loop Chicago

Downtown Chicago

Tomas

$137 nightly

$161 total

Sep 7 - Sep 8

Total with taxes and fees

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

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

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

9. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Melanie

$181 nightly

$216 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 hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

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.

10. River Hotel

Downtown Chicago

Timothy

$159 nightly

$190 total

Sep 8 - Sep 9

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 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.

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

$163 nightly

$192 total

Sep 7 - Sep 8

Total with taxes and fees

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

A grilled pineapple on top of a stack of meat, served on a pan.

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

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

12. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

$212 nightly

$252 total

Sep 7 - Sep 8

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

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

13. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Odessia

$154 nightly

$183 total

Sep 7 - Sep 8

Total with taxes and fees

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

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.

A restaurant with booths, tables, and a green wall in the background.

14. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Matthew

$143 nightly

$170 total

Sep 8 - Sep 9

Total with taxes and fees

A grand lobby with ornate ceiling artwork, chandeliers, and a central staircase.

A grand hall with a central aisle, ornate chandeliers, and rows of chairs.

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

A grand lobby with ornate ceiling artwork, chandeliers, and a prominent 'P' emblem.

15. Palmer House a Hilton Hotel

Downtown Chicago

$209 nightly

$248 total

Sep 9 - Sep 10

Total with taxes and fees

A hotel bathroom with a large mirror, a sink, and a vanity.

A hotel with a classic facade, large windows, and a prominent entrance.

A hotel room with a view of a cityscape through a large window, a floor lamp, a sofa with cushions, and a small table with a plant.

A bakery display with pastries and a coffee shop sign in the background.

16. Sports Illustrated Resorts Chicago

Downtown Chicago

Jose Rafael

$248 nightly

$295 total

Sep 10 - Sep 11

Total with taxes and fees

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

A modern living room with a dark sofa set, a glass coffee table, and a decorative chandelier.

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

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

17. Silversmith Hotel Chicago Downtown

Downtown Chicago

Xiao

$195 nightly

$232 total

Sep 9 - Sep 10

Total with taxes and fees

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

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

A coffee shop interior with a display case of pastries, a coffee machine, and a menu board.

18. Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

$144 nightly

$171 total

Sep 7 - Sep 8

Total with taxes and fees

A hotel with a modern glass facade, a prominent Hampton Inn sign, and a Homewood Suites by Hilton sign.

A hotel room with a large window offering a cityscape view, including a prominent building with a clock tower.

A hotel room with a large window offering a city view, a sofa, a chair, a small table, and a desk with a chair.

A modern hotel lobby with a long reception desk, seating area, and large windows offering city views.

19. Hampton Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

Jon

$139 nightly

$166 total

Sep 7 - Sep 8

Total with taxes and fees

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

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

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

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

20. citizenM Chicago Downtown

Downtown Chicago

lakadria

$170 nightly

$202 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

Hyatt Regency Chicago

10/10 Excellent

"Na"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"A fantastic day experience."

Congress Plaza Hotel

10/10 Excellent

"It was great! We arrived early and the front desk was able to check us in early and our room and view was just amazing! Loved how clean everything was."

L7 Chicago by LOTTE

10/10 Excellent

"The room was very neat & clean upon arrival. The staff were kind and readily available for anything you need. It was a relaxing and comfortable stay. The location is perfect at the center of everything or just a few train stops away. Would stay again"

Kasa Magnificent Mile Chicago

10/10 Excellent

"I felt comfortable during my stay at Kasa. There was a lot of room space and having a balcony was great"

Hilton Chicago

10/10 Excellent

"I was upgraded to a larger room with amazing views upon request for my birthday weekend stay ! All of the staff were friendly and professional and Willie with housekeeping was especially helpful getting me an extra blanket and making some local recommendations for food and attractions. He was very kind and a real asset to the hotel staff . My server Juan in the 720 restaurant was also very nice . The breakfast buffet was excellent, a little pricey but includes all drinks including fresh OJ . The bacon and pancakes were delicious. I didn’t try the other restaurant Kittys . Only the rooms facing the street have views so keep that in mind when booking a room otherwise you’ll be facing a wall . The rooms are clean and beds are pretty comfortable . All in all a very good stay"

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Amazing hotel ! Was in the midst of everything and the staff was extremely helpful and even upgraded our room! Would definitely book again"

Warwick Allerton - Chicago

10/10 Excellent

"Great location! Excellent staff, clean room."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"This place was amazing"

More cheap stays in Southwest Side

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL

$57 nightly

$64 total

Sep 20 - Sep 21

Total with taxes and fees

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

$63 nightly

$70 total

Sep 9 - Sep 10

Total with taxes and fees

6.4/10 (1,256 reviews)

Quality Inn & Suites Orland Park - Chicago

8800 W 159th St Orland Park IL

$83 nightly

$93 total

Sep 27 - Sep 28

Total with taxes and fees

7.4/10 Good! (1,009 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

$141 nightly

$164 total

Sep 7 - Sep 8

Total with taxes and fees

8/10 Very Good! (1,000 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

$139 nightly

$166 total

Sep 7 - Sep 8

Total with taxes and fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

$143 nightly

$170 total

Sep 8 - Sep 9

Total with taxes and fees

Hotels in Southwest Side with star-rating

Explore a world of travel with Expedia

Lodging

Find hotels in Southwest Side, IL from $64

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. Congress Plaza Hotel

5. Hilton Chicago

6. The Chicago Hotel Collection Ambassador Gold Coast

7. Best Western Grant Park Hotel

8. LIVN - West Loop Chicago

9. Hilton Vacation Club Hotel Blake Chicago

10. River Hotel

11. Hilton Garden Inn Chicago Downtown South Loop

12. Hyatt Centric The Loop Chicago

13. Aloft by Marriott Chicago Mag Mile

14. Travelodge by Wyndham Downtown Chicago

15. Palmer House a Hilton Hotel

16. Sports Illustrated Resorts Chicago

17. Silversmith Hotel Chicago Downtown

18. Courtyard by Marriott Chicago Magnificent Mile

19. Hampton Inn Chicago Downtown/Magnificent Mile

20. citizenM Chicago Downtown

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

Hyatt Regency Chicago

InterContinental Chicago Magnificent Mile by IHG

Congress Plaza Hotel

L7 Chicago by LOTTE

Kasa Magnificent Mile Chicago

Hilton Chicago

The Royal Sonesta Chicago Downtown

Warwick Allerton - Chicago

The Chicago Hotel Collection - Magnificent Mile

More cheap stays in Southwest Side

Motel 6 Naperville, IL

Red Roof Inn PLUS+ Chicago - Willowbrook

Quality Inn & Suites Orland Park - Chicago

Holiday Inn Chicago – Midway Airport S by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Travelodge by Wyndham Downtown Chicago

Hotels in Southwest Side with star-rating

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