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.

A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

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

1. Congress Plaza Hotel

Downtown Chicago

John

$188 nightly

$223 total

Sep 27 - Sep 28

Total with taxes and fees

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

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.

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

2. Hotel Riu Plaza Chicago

Downtown Chicago

Sean Robert

$289 nightly

$343 total

Oct 13 - Oct 14

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 high ceilings, large arched windows, and a grand staircase.

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

3. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Michael T.

$197 nightly

$234 total

Sep 27 - Sep 28

Total with taxes and fees

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

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.

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

4. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

$216 nightly

$257 total

Oct 1 - Oct 2

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

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

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

5. Omni Chicago Hotel

Downtown Chicago

Shiaka

$302 nightly

$359 total

Oct 15 - Oct 16

Total with taxes and fees

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

A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

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.

6. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Lauryn

$188 nightly

$223 total

Oct 13 - Oct 14

Total with taxes and fees

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

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

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.

7. Hilton Chicago

Downtown Chicago

Alan

$208 nightly

$248 total

Oct 23 - Oct 24

Total with taxes and fees

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

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

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

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

Isabella

$176 nightly

$209 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 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.

9. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Tremecka

$147 nightly

$173 total

Sep 27 - Sep 28

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

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

10. Eurostars Magnificent Mile

Downtown Chicago

Tony

$200 nightly

$238 total

Sep 27 - Sep 28

Total with taxes and fees

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

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

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

11. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Kurt

$247 nightly

$294 total

Sep 27 - Sep 28

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

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

12. citizenM Chicago Downtown

Downtown Chicago

Isayra

$229 nightly

$272 total

Sep 27 - Sep 28

Total with taxes and fees

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

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

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

A bookshelf with books, decorative items, and plants.

13. Freehand Chicago

Downtown Chicago

Steven

$226 nightly

$268 total

Oct 6 - Oct 7

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 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.

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

14. L7 Chicago by LOTTE

Downtown Chicago

GUILLERMO

$287 nightly

$341 total

Sep 27 - Sep 28

Total with taxes and fees

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

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

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

$286 nightly

$340 total

Sep 27 - Sep 28

Total with taxes and fees

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

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

A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

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

16. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Michael

$126 nightly

$149 total

Sep 27 - Sep 28

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

Kenan

$309 nightly

$368 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-level indoor area with a central water feature, surrounded by seating areas and greenery.

A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.

18. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Shweta

$214 nightly

$255 total

Sep 27 - Sep 28

Total with taxes and fees

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

A modern living room with a sofa, coffee table, and ottoman, a fireplace, and a large window with a city view.

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

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

19. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Sunny

$373 nightly

$437 total

Oct 4 - Oct 5

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 modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

20. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Phillip

$189 nightly

$224 total

Sep 27 - Sep 28

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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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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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

Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Rooms very clean. Staff very friendly and helpful… will definitely stay here again"

Chicago Marriott Midway

10/10 Excellent

"Great experience"

SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent

"Good location, safe, convenient, clean"

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"location is fantastic, staff very helpful, traveled with my pet and no issues whatsoever."

Chicago Lake Shore Hotel

10/10 Excellent

"My stay at the Chicago Lake Shore Hotel was good! The outside of the facility looks to be in rough shape but once you step inside the rooms they are updated and very clean!!! I would stay here again for the price. Of they could update/renovate the outside this place would be 10/10!!!"

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"amazing and friendly staff"

Sophy Hyde Park

10/10 Excellent

"XXX"

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

10/10 Excellent

"Staff was very accommodating. The breakfast was ok."

Rainbow Motel

10/10 Excellent

"Good Location with plenty of walkable places. Lots of restaurants and stores nearby which is always a plus. No microwave in the room but the mini fridge worked wonderfully. Lots of options on the TV as well. Staff was very nice and welcoming. Overall a very nice experience. Very good option for anyone looking for a more affordable option. Would definitely recommend."

More cheap stays in South Side

Rainbow Motel

7050 W Archer Ave Chicago IL

$86 nightly

$100 total

Sep 24 - Sep 25

Total with taxes and fees

5.4/10 (60 reviews)

Saratoga Motel By Capital O Near Midway Airport Chicago IL

7701, S Cicero Avenue Chicago IL

$95 nightly

$110 total

Sep 24 - Sep 25

Total with taxes and fees

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

$100 nightly

$117 total

Sep 24 - Sep 25

Total with taxes and fees

Carlton Inn Midway

4944 S Archer Ave Chicago IL

$119 nightly

$140 total

Sep 24 - Sep 25

Total with taxes and fees

6/10 (1,001 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

$162 nightly

$188 total

Sep 27 - Sep 28

Total with taxes and fees

8.2/10 Very Good! (1,000 reviews)

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

6500 S Cicero Ave Chicago IL

$180 nightly

$211 total

Sep 27 - Sep 28

Total with taxes and fees

9/10 Wonderful! (1,369 reviews)

Hotels in South Side with star-rating

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Things to do in Chicago

Find hotels in South Side, IL from $100

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. 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

Rainbow Beach

Learn more about South Side

Top South Side Hotel Reviews

Best Western Inn & Suites - Midway Airport

Chicago Marriott Midway

SpringHill Suites by Marriott Chicago Chinatown

Hyatt Place Chicago-South/University Medical Center

Chicago Lake Shore Hotel

Holiday Inn Chicago – Midway Airport S by IHG

Sophy Hyde Park

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

Rainbow Motel

More cheap stays in South Side

Rainbow Motel

Saratoga Motel By Capital O Near Midway Airport Chicago IL

Motel 6 - Chicago, IL

Carlton Inn Midway

Holiday Inn Chicago – Midway Airport S by IHG

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

Hotels in South Side with star-rating

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