Top 10 Hotels in South Side (from $102) 2026 - Competitive Prices

A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

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Our top choices for South Side hotels

A balcony with a table and chairs, a bottle of wine, and a glass of wine.

A modern living room with a sofa, a coffee table, a laptop, and a city view through large windows.

A dining area with a wooden table and white chairs, large windows with blinds, and a vase with flowers on the table.

A hotel lobby with a revolving door, a reception desk, and a waiting area with seating.

1. Kasa Magnificent Mile Chicago

Downtown Chicago

Brooke

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.

2. Congress Plaza Hotel

Downtown Chicago

Ashya

$108 nightly

$129 total

Nov 11 - Nov 12

Total with taxes and fees

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

A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

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.

3. Hotel Riu Plaza Chicago

Downtown Chicago

Suki

$209 nightly

$249 total

Nov 11 - Nov 12

Total with taxes and fees

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

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

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

4. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Christian

$121 nightly

$143 total

Nov 11 - Nov 12

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.

5. Hilton Chicago

Downtown Chicago

Anna

$194 nightly

$230 total

Nov 13 - Nov 14

Total with taxes and fees

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

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.

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

6. River Hotel

Downtown Chicago

Rebecca

$152 nightly

$181 total

Nov 1 - Nov 2

Total with taxes and fees

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

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.

A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.

7. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Vincenzo

$161 nightly

$191 total

Nov 1 - Nov 2

Total with taxes and fees

A room with two chairs and a small table, a large window with a city view at night.

A modern living room with a sectional sofa, a round ottoman, a dining area with chairs and a table, and a large mirror on the wall.

A bar area with a long counter, multiple stools, and a television screen.

A modern bar area with a circular seating arrangement, a staircase leading to an upper level, and a view of the city through large windows.

8. Eurostars Magnificent Mile

Downtown Chicago

Will

$152 nightly

$181 total

Nov 1 - Nov 2

Total with taxes and fees

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.

A bar area with a long counter, multiple shelves of bottles, and four bar stools.

9. L7 Chicago by LOTTE

Downtown Chicago

Jeffrey Thomas

$184 nightly

$218 total

Nov 1 - Nov 2

Total with taxes and fees

An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.

The Chicago Hotel Collection building with a glass facade, American flag, and signage for Barista Bar and Seighity events.

A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.

A rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.

10. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Frankieta

$142 nightly

$169 total

Nov 1 - Nov 2

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

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

11. Hyatt Regency Chicago

Downtown Chicago

Addison

$268 nightly

$319 total

Oct 31 - Nov 1

Total with taxes and fees

A hotel with a classic facade, multiple flags, and a prominent entrance.

A spacious lobby with a grand staircase, a large abstract painting, and a seating area with modern furniture.

A spacious hotel lobby with a bar area, dining tables, and a central seating area.

12. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

David

$169 nightly

$201 total

Nov 15 - Nov 16

Total with taxes and fees

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.

A multi-level indoor area with a central water feature, surrounded by seating areas and greenery.

A swimming pool with a glass wall, a seating area with sofas, and an exit sign.

13. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

$152 nightly

$181 total

Nov 1 - Nov 2

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 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.

14. citizenM Chicago Downtown

Downtown Chicago

Katarina

$170 nightly

$202 total

Nov 1 - Nov 2

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

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

15. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Sandra

$112 nightly

$131 total

Nov 11 - Nov 12

Total with taxes and fees

A dining area with a table set for four, large windows offering a cityscape view at dusk.

A modern interior with a central fireplace, seating area, and wall-mounted lighting.

A breakfast table with croissants, a bowl of berries, a glass of orange juice, and a smoothie, set against a cityscape view through a window.

A high-rise hotel room with large windows offering a city view, round tables set for dining, and elegant decor with flowers and candles.

16. The Royal Sonesta Chicago Downtown

Downtown Chicago

Jordyn

$196 nightly

$233 total

Nov 1 - Nov 2

Total with taxes and fees

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

A bar area with a long counter, blue bar stools, and a variety of bottles and glasses.

A modern room with a view of a river and high-rise buildings.

17. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

James

$250 nightly

$294 total

Nov 1 - Nov 2

Total with taxes and fees

A luxurious hotel lobby with a plush sofa set, a large wooden bookshelf, and a central decorative pillar.

A bar area with a staircase leading up to it, surrounded by potted plants.

A reception area with a wooden counter, shelves with various items, and a decorative wall hanging.

A warmly lit library with bookshelves, a central reading area with sofas and a table, and a chandelier.

18. Freehand Chicago

Downtown Chicago

George

$185 nightly

$220 total

Nov 2 - Nov 3

Total with taxes and fees

The Intercontinental hotel facade with a large American flag and a floral display.

A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.

A person sitting by a window with a cityscape view.

A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

19. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Said Lopez

$241 nightly

$287 total

Oct 31 - Nov 1

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

A modern lobby with a seating area, a bar, and a green wall.

Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.

A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.

20. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Poua

$130 nightly

$153 total

Nov 1 - Nov 2

Total with taxes and fees

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Stay near popular South Side attractions

A cityscape with historic buildings, a prominent church, and a view of the ocean.

University of Chicago

8.6/10 (3,689 reviews)

Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

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A baseball stadium with advertisements, including 'xfinity' and 'proven IT'.

Rate Field

8.6/10 (235 reviews)

Catch an event at Rate Field during your trip to Chicago. Experience the entertainment choices and acclaimed theater scene in this vibrant area.

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A classical building with a dome and columns, featuring Charlie Brown exhibit banners.

Griffin Museum of Science and Industry

9.2/10 (1,796 reviews)

This large, interactive museum contains a coal mine and World War II submarine among its many attractions.

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A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

Jackson Park

7.4/10 (9 reviews)

Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.

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A train passing through a tunnel with a curved roof and string lights.

Illinois Institute of Technology

7.0/10 (4 reviews)

Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.

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Rainbow Beach

Why not spend a lazy afternoon at Rainbow Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.

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Obama Presidential Center

You can spend an afternoon exploring the galleries in Obama Presidential Center during your trip to Chicago. Wander the beaches and gardens while you're in the area.

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Harold Washington Cultural Center

Enjoy an outing to Harold Washington Cultural Center during your stay in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

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Learn more about South Side

Discover the metropolitan area of South Side—museums, skyscrapers, and top sights like Lake Michigan.

See all hotels in South Side

Top South Side Hotel Reviews

Chicago Lake Shore Hotel

10/10 Excellent

"It was nice, we did not stay in the hotel for long, but the price was fair for the room condition"

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent

"The staff is knowledgeable, friendly, and very helpful."

SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"The rooms in hotel was very clean. The staff was friendly and helpful. They had parking on premises. And the breakfast was very nice."

Chicago Marriott Midway

10/10 Excellent

"Love"

Villa Dubois Guest House

10/10 Excellent

"The room and interior are nice. There weren’t other people when I was staying. Getting in was easy. The place was clean."

Rainbow Motel

8/10 Good

"Be careful not to get one of the themed rooms. We got the space ship room and it looked nothing like the picture on the website. If you get a regular room it's amazing."

Mccormick Place Guest House

10/10 Excellent

"Was a very nice clean n quiet stay…Would definitely recommend n stay again if plan on visiting Chicago nxt time!"

Admiral Motel By Oyo Chicago I-94

10/10 Excellent

"Air conditioner was broken, toilet was leaking from the floor, but staff, guests and neighbours were very friendly. Overall good given the affordable cost. Not a five star hotel, but doesn’t pretend to be"

More cheap stays in South Side

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

$90 nightly

$106 total

Oct 20 - Oct 21

Total with taxes and fees

7/10 Good! (518 reviews)

Rainbow Motel

7050 W Archer Ave Chicago IL

$93 nightly

$109 total

Oct 19 - Oct 20

Total with taxes and fees

5.4/10 (68 reviews)

Best Motel By OYO Chicago I-90

6535 S King Dr Chicago IL

$94 nightly

$110 total

Oct 18 - Oct 19

Total with taxes and fees

3.4/10 (156 reviews)

Carlton Inn Midway

4944 S Archer Ave Chicago IL

$107 nightly

$126 total

Oct 20 - Oct 21

Total with taxes and fees

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

6500 S Cicero Ave Chicago IL

$135 nightly

$159 total

Nov 15 - Nov 16

Total with taxes and fees

9/10 Wonderful! (1,369 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

$145 nightly

$168 total

Nov 1 - Nov 2

Total with taxes and fees

Hotels in South Side with star-rating

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Things to do in Chicago

Find hotels in South Side, IL from $102

Upfront pricing

Treat yourself

Be picky

Go beyond your typical stay in South Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for South Side hotels

1. Kasa Magnificent Mile Chicago

2. Congress Plaza Hotel

3. Hotel Riu Plaza Chicago

4. The Chicago Hotel Collection Ambassador Gold Coast

5. Hilton Chicago

6. River Hotel

7. Hilton Chicago/Magnificent Mile Suites

8. Eurostars Magnificent Mile

9. L7 Chicago by LOTTE

10. The Chicago Hotel Collection - Magnificent Mile

11. Hyatt Regency Chicago

12. The Allegro Royal Sonesta Hotel Chicago Loop

13. Embassy Suites by Hilton Chicago Downtown River North

14. citizenM Chicago Downtown

15. Travelodge by Wyndham Downtown Chicago

16. The Royal Sonesta Chicago Downtown

17. LondonHouse Chicago, Curio Collection by Hilton

18. Freehand Chicago

19. InterContinental Chicago Magnificent Mile by IHG

20. DoubleTree by Hilton Chicago - Magnificent Mile

Stay near popular South Side attractions

University of Chicago

Rate Field

Griffin Museum of Science and Industry

Jackson Park

Illinois Institute of Technology

Rainbow Beach

Obama Presidential Center

Harold Washington Cultural Center

Learn more about South Side

Top South Side Hotel Reviews

Chicago Lake Shore Hotel

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

SpringHill Suites by Marriott Chicago Chinatown

Chicago Marriott Midway

Villa Dubois Guest House

Rainbow Motel

Mccormick Place Guest House

Admiral Motel By Oyo Chicago I-94

More cheap stays in South Side

Motel 6 - Chicago, IL

Rainbow Motel

Best Motel By OYO Chicago I-90

Carlton Inn Midway

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Chicago – Midway Airport S by IHG

Hotels in South Side with star-rating

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