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

1. Congress Plaza Hotel

Downtown Chicago

John

$159 nightly

$189 total

Sep 27 - Sep 28

Total with taxes and fees

2. Hotel Riu Plaza Chicago

Downtown Chicago

Mya

$270 nightly

$321 total

Oct 13 - Oct 14

Total with taxes and fees

3. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Michael T.

$160 nightly

$191 total

Sep 29 - Sep 30

Total with taxes and fees

42-inch flat-screen TV with cable channels, TV, pay movies

4. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

$203 nightly

$242 total

Sep 27 - Sep 28

Total with taxes and fees

5. Omni Chicago Hotel

Downtown Chicago

Shiaka

$314 nightly

$373 total

Oct 15 - Oct 16

Total with taxes and fees

2 restaurants; breakfast and dinner served

6. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Whitney

$152 nightly

$181 total

Sep 29 - Sep 30

Total with taxes and fees

7. Hilton Chicago

Downtown Chicago

Alan

$236 nightly

$281 total

Sep 27 - Sep 28

Total with taxes and fees

8. River Hotel

Downtown Chicago

Isabella

$187 nightly

$222 total

Sep 27 - Sep 28

Total with taxes and fees

In-room safe, laptop workspace, cribs (free), WiFi (free)

9. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Tremecka

$170 nightly

$200 total

Sep 27 - Sep 28

Total with taxes and fees

10. Eurostars Magnificent Mile

Downtown Chicago

Tony

$224 nightly

$266 total

Sep 20 - Sep 21

Total with taxes and fees

11. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Kurt

$230 nightly

$273 total

Sep 20 - Sep 21

Total with taxes and fees

Premium Room, 1 King Bed (View) | Premium bedding, pillowtop beds, in-room safe, desk

12. citizenM Chicago Downtown

Downtown Chicago

Isayra

$199 nightly

$237 total

Sep 20 - Sep 21

Total with taxes and fees

13. Freehand Chicago

Downtown Chicago

Steven

$226 nightly

$268 total

Oct 12 - Oct 13

Total with taxes and fees

55-inch LCD TV with cable channels, TV, pay movies

Breakfast, lunch, dinner and brunch served

14. L7 Chicago by LOTTE

Downtown Chicago

Andrea

$275 nightly

$327 total

Sep 21 - Sep 22

Total with taxes and fees

15. The Royal Sonesta Chicago Downtown

Downtown Chicago

ShaRona

$259 nightly

$298 total

Sep 20 - Sep 21

Total with taxes and fees

Standard Room, 1 King Bed | View from room

16. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Jacqueline

$153 nightly

$181 total

Sep 20 - Sep 21

Total with taxes and fees

2 restaurants; breakfast, lunch, dinner, and brunch served

17. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Darryl Halbert

$309 nightly

$367 total

Sep 20 - Sep 21

Total with taxes and fees

18. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Shweta

$217 nightly

$258 total

Sep 27 - Sep 28

Total with taxes and fees

2 restaurants; breakfast, lunch, and dinner served

1 King Bed, 1 Bedroom Suite | Living area | 55-inch LED TV with premium channels, TV, first-run movies

Presidential Suite, 1 King Bed, Accessible | Frette Italian sheets, premium bedding, in-room safe, blackout drapes

19. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Sunny

$355 nightly

$417 total

Sep 27 - Sep 28

Total with taxes and fees

20. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Victoria

$169 nightly

$201 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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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.

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Top South Side Hotel Reviews

Chinatown Hotel Chicago

10/10 Excellent

"China Town Chicago is my new favorite location in the state of Illinois"

Rainbow Motel

10/10 Excellent

"Very clean nice employees"

Sophy Hyde Park

8/10 Good

"What an amazing stay! This hotel was absolutely wonderful from start to finish. The accommodations were beautiful and comfortable, the staff was friendly and welcoming, and the entire experience exceeded my expectations. I truly enjoyed every moment of my stay and would definitely return. Highly recommend this hotel for a relaxing and memorable experience!"

Motel 6 - Chicago, IL

10/10 Excellent

"Pleasant stay! Would recommend 10/10"

Carlton Inn Midway

10/10 Excellent

"Excellent breakfast, best shuttle service, Excellent hospitality."

Saratoga Motel By Capital O Near Midway Airport Chicago IL

10/10 Excellent

"Had a good stay here will be going back. The night staff was very helpful and nice and they wasn’t at my door at 11 rushing us to leave to was able to pack and leave in peace I appreciate that so much."

Villa Dubois Guest House

10/10 Excellent

"It was a really nice stay; as a first-time traveller, it was close to Soldier Field stadium, where most concerts are held. I also loved the room; it was really nice and clean, and super easy to find everything."

Mccormick Place Guest House

8/10 Good

"Great property."

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"