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 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.

1. Congress Plaza Hotel

Downtown Chicago

John

$157 nightly

$187 total

Oct 26 - Oct 27

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 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.

2. River Hotel

Downtown Chicago

Jared

$186 nightly

$221 total

Oct 25 - Oct 26

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

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

3. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Marta

$179 nightly

$213 total

Oct 14 - Oct 15

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.

4. Hotel Riu Plaza Chicago

Downtown Chicago

Sean Robert

$260 nightly

$310 total

Oct 25 - Oct 26

Total with taxes and fees

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

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.

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

5. Hilton Chicago

Downtown Chicago

Alan

$185 nightly

$220 total

Oct 24 - Oct 25

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

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

Lauryn

$179 nightly

$213 total

Oct 25 - Oct 26

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

7. Eurostars Magnificent Mile

Downtown Chicago

Tony

$202 nightly

$240 total

Oct 27 - Oct 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.

8. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Kurt

$199 nightly

$236 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.

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

9. Hyatt Regency Chicago

Downtown Chicago

Whitney

$346 nightly

$411 total

Oct 25 - Oct 26

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

10. L7 Chicago by LOTTE

Downtown Chicago

GUILLERMO

$299 nightly

$355 total

Oct 1 - Oct 2

Total with taxes and fees

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

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

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

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

11. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Tremecka

$166 nightly

$195 total

Oct 26 - Oct 27

Total with taxes and fees

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

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.

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

12. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

$174 nightly

$207 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

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

A bookshelf with books, decorative items, and plants.

13. Freehand Chicago

Downtown Chicago

Steven

$226 nightly

$268 total

Oct 12 - Oct 13

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 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.

14. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Sharee

$276 nightly

$328 total

Oct 25 - Oct 26

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

15. citizenM Chicago Downtown

Downtown Chicago

Kimberly

$206 nightly

$245 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

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.

16. The Royal Sonesta Chicago Downtown

Downtown Chicago

ShaRona

$276 nightly

$328 total

Oct 25 - Oct 26

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

17. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Julian

$126 nightly

$149 total

Oct 25 - Oct 26

Total with taxes and fees

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

A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

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

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

18. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Kenan

$276 nightly

$329 total

Oct 25 - Oct 26

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.

19. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Shweta

$213 nightly

$253 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

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

A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

20. DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Madelyn

$195 nightly

$231 total

Oct 25 - Oct 26

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

Chicago Lake Shore Hotel

8/10 Good

"Toilet very low, maybe add lift bars in the bathroom, AC unit noise ,hard to hear TV, all staff we encountered very helpful.Beds very comfortable."

Carlton Inn Midway

8/10 Good

"El lugar en general está muy bien ubicado si necesitas llegar al aeropuerto, pero es algo viejo y el aire acondicionado suela mucho . El desayuno estuvo muy bien"

Villa Dubois Guest House

10/10 Excellent

"Nice and clean and easy parking"

Jaslin Hotel

10/10 Excellent

"- Friendly check-in - Clean lobby, elevator and hallways - No wait elevator - Clean quiet spacious room - Comfortable bed with quality bed linens - Sparkling clean bathroom with quality bath linens - Easily assessable and dependable WIFI - Coffee maker and fridge - Friendly checkout."

Mccormick Place Guest House

8/10 Good

"I had a wonderful stay at the DuBois McCormick Place Guest House. The location was very convenient, especially for visiting McCormick Place and exploring the surrounding area. The room was clean, comfortable, and well maintained. I also appreciated the peaceful atmosphere and the overall attention to detail. The guest house offered a comfortable home base after a busy day, with everything needed for a pleasant stay. I would happily recommend the DuBois McCormick Place Guest House to both business and leisure travelers, and I look forward to staying there again."

Best Western Inn & Suites - Midway Airport

10/10 Excellent

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

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."

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

Rainbow Motel

7050 W Archer Ave Chicago IL

$86 nightly

$100 total

Sep 28 - Sep 29

Total with taxes and fees

5.4/10 (60 reviews)

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

$90 nightly

$106 total

Oct 13 - Oct 14

Total with taxes and fees

Best Motel By OYO Chicago I-90

6535 S King Dr Chicago IL

$94 nightly

$110 total

Sep 28 - Sep 29

Total with taxes and fees

Carlton Inn Midway

4944 S Archer Ave Chicago IL

$119 nightly

$140 total

Sep 28 - Sep 29

Total with taxes and fees

6/10 (1,009 reviews)

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

$149 nightly

$173 total

Oct 26 - Oct 27

Total with taxes and fees

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

6500 S Cicero Ave Chicago IL

$159 nightly

$187 total

Oct 25 - Oct 26

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 $100

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. River Hotel

3. The Chicago Hotel Collection Ambassador Gold Coast

4. Hotel Riu Plaza Chicago

5. Hilton Chicago

6. The Chicago Hotel Collection - Magnificent Mile

7. Eurostars Magnificent Mile

8. The Allegro Royal Sonesta Hotel Chicago Loop

9. Hyatt Regency Chicago

10. L7 Chicago by LOTTE

11. Travelodge by Wyndham Downtown Chicago

12. Hilton Chicago/Magnificent Mile Suites

13. Freehand Chicago

14. LondonHouse Chicago, Curio Collection by Hilton

15. citizenM Chicago Downtown

16. The Royal Sonesta Chicago Downtown

17. Club Quarters Hotel, Central Loop, Chicago

18. InterContinental Chicago Magnificent Mile by IHG

19. Embassy Suites by Hilton Chicago Downtown River North

20. DoubleTree by Hilton Chicago - Magnificent Mile

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

Chicago Lake Shore Hotel

Carlton Inn Midway

Villa Dubois Guest House

Jaslin Hotel

Mccormick Place Guest House

Best Western Inn & Suites - Midway Airport

Rainbow Motel

Admiral Motel By Oyo Chicago I-94

More cheap stays in South Side

Rainbow Motel

Motel 6 - Chicago, IL

Best Motel By OYO Chicago I-90

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

Explore a world of travel with Expedia