Top 10 Hotels in South Side (from $100) 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 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.

1. Congress Plaza Hotel

Downtown Chicago

Manuel

$151 nightly

$180 total

Sep 10 - Sep 11

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

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

2. Hotel Riu Plaza Chicago

Downtown Chicago

Jarred

$231 nightly

$275 total

Sep 10 - Sep 11

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

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

3. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Laura

$156 nightly

$185 total

Sep 21 - Sep 22

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

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

4. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Jeremy

$197 nightly

$234 total

Sep 10 - Sep 11

Total with taxes and fees

A dining area with tables set for four, large windows with a view of city buildings, and a curved ceiling structure.

A hotel room with a large bed, a desk with a lamp, a bench, and a view of the cityscape through large windows.

A spacious lobby with a patterned carpet, wooden paneling, and modern lighting fixtures.

A multi-story building with a prominent storefront featuring a golden sign.

5. Omni Chicago Hotel

Downtown Chicago

Linda

$267 nightly

$317 total

Oct 1 - Oct 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.

6. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Patricia

$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 modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

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

$224 nightly

$266 total

Sep 10 - Sep 11

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

8. River Hotel

Downtown Chicago

steve

$181 nightly

$216 total

Sep 27 - Sep 28

Total with taxes and fees

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

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.

A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.

9. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Matthew

$147 nightly

$173 total

Sep 10 - Sep 11

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 hotel lobby with a large window, seating area, and a reception desk.

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.

10. Eurostars Magnificent Mile

Downtown Chicago

Brennique

$200 nightly

$238 total

Sep 27 - Sep 28

Total with taxes and fees

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

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

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

11. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Michaela

$244 nightly

$290 total

Oct 4 - Oct 5

Total with taxes and fees

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

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

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.

12. citizenM Chicago Downtown

Downtown Chicago

Germaine

$197 nightly

$234 total

Sep 20 - Sep 21

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

A bookshelf with books, decorative items, and plants.

13. Freehand Chicago

Downtown Chicago

Jared

$224 nightly

$266 total

Sep 23 - Sep 24

Total with taxes and fees

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

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 against a window overlooking a cityscape. There is a small table with a book, a vase with flowers, and a cup.

14. L7 Chicago by LOTTE

Downtown Chicago

christina

$287 nightly

$341 total

Oct 1 - Oct 2

Total with taxes and fees

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

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

A rooftop terrace with outdoor seating and a fire pit, overlooking a cityscape with tall buildings.

15. The Royal Sonesta Chicago Downtown

Downtown Chicago

ShaRona

$271 nightly

$322 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 hotel room with a large window, a bed, and a suitcase.

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

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

16. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Jacqueline

$163 nightly

$194 total

Sep 10 - Sep 11

Total with taxes and fees

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

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

A person sitting by a window with a cityscape view.

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

17. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Anfal

$343 nightly

$408 total

Sep 27 - Sep 28

Total with taxes and fees

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

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

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.

18. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Kristeen

$189 nightly

$225 total

Sep 10 - Sep 11

Total with taxes and fees

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

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

A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.

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

19. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Kamal

$303 nightly

$360 total

Sep 20 - Sep 21

Total with taxes and fees

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

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

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 hotel room with a large bed, a desk with a computer, a TV, and a seating area with a chair and ottoman.

20. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Phillip

$197 nightly

$234 total

Sep 20 - Sep 21

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 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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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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Barack Obama Residence

You can find out about the history of Chicago when you stop by Barack Obama Residence. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

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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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Ida B Wells House

You can find out about the history of Chicago with a stop at Ida B Wells House. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

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Learn more about South Side

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

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"Great property."

Rainbow Motel

Sep 27 - Sep 28

Total with taxes and fees

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

6500 S Cicero Ave Chicago IL

$193 nightly

$227 total

Sep 27 - Sep 28

Total with taxes and fees

9/10 Wonderful! (1,367 reviews)

Hotels in South Side with star-rating

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Find hotels in South Side, IL from $100

Go beyond your typical stay in South Side

Check prices for these dates

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Our top choices for South Side hotels

1. Congress Plaza Hotel

2. Hotel Riu Plaza Chicago

3. The Chicago Hotel Collection Ambassador Gold Coast

4. Hilton Chicago/Magnificent Mile Suites

5. Omni Chicago Hotel

6. The Chicago Hotel Collection - Magnificent Mile

7. Hilton Chicago

8. River Hotel

9. Travelodge by Wyndham Downtown Chicago

10. Eurostars Magnificent Mile

11. The Allegro Royal Sonesta Hotel Chicago Loop

12. citizenM Chicago Downtown

13. Freehand Chicago

14. L7 Chicago by LOTTE

15. The Royal Sonesta Chicago Downtown

16. Club Quarters Hotel, Central Loop, Chicago

17. InterContinental Chicago Magnificent Mile by IHG

18. Embassy Suites by Hilton Chicago Downtown River North

19. LondonHouse Chicago, Curio Collection by Hilton

20. Crowne Plaza Chicago West Loop by IHG

Stay near popular South Side attractions

University of Chicago

Rate Field

Griffin Museum of Science and Industry

Illinois Institute of Technology

Jackson Park

Barack Obama Residence

Obama Presidential Center

Ida B Wells House

Learn more about South Side

Top South Side Hotel Reviews

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Rainbow Motel

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Rainbow Motel

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Hotels in South Side with star-rating

Explore a world of travel with Expedia