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Our top choices for South Side hotels

1. Congress Plaza Hotel

Downtown Chicago

Christina

$145 nightly

Aug 30 - Aug 31

Total with taxes and fees

2. Hotel Riu Plaza Chicago

Downtown Chicago

Cicely

$232 nightly

Aug 30 - Aug 31

Total with taxes and fees

3. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Judy

$152 nightly

Aug 17 - Aug 18

Total with taxes and fees

4. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

CHRISTIAN GIOVANNI

$161 nightly

Aug 30 - Aug 31

Total with taxes and fees

5. Omni Chicago Hotel

Downtown Chicago

Melissa

$211 nightly

Aug 23 - Aug 24

Total with taxes and fees

6. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Shawna

$161 nightly

Aug 10 - Aug 11

Total with taxes and fees

7. Hilton Chicago

Downtown Chicago

kun

$219 nightly

Aug 30 - Aug 31

Total with taxes and fees

8. River Hotel

Downtown Chicago

Yousef

$160 nightly

Aug 31 - Sep 1

Total with taxes and fees

9. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Adam

$115 nightly

Aug 31 - Sep 1

Total with taxes and fees

10. Eurostars Magnificent Mile

Downtown Chicago

Kristine

$200 nightly

Aug 25 - Aug 26

Total with taxes and fees

11. The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Mucio

$222 nightly

Aug 30 - Aug 31

Total with taxes and fees

12. citizenM Chicago Downtown

Downtown Chicago

lakadria

$179 nightly

Aug 30 - Aug 31

Total with taxes and fees

13. Freehand Chicago

Downtown Chicago

james

$117 nightly

Aug 31 - Sep 1

Total with taxes and fees

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

14. L7 Chicago by LOTTE

Downtown Chicago

Julie Ann

$278 nightly

Aug 13 - Aug 14

Total with taxes and fees

15. The Royal Sonesta Chicago Downtown

Downtown Chicago

Alexis

$211 nightly

Sep 1 - Sep 2

Total with taxes and fees

16. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Kelli

$143 nightly

Aug 30 - Aug 31

Total with taxes and fees

17. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Jose

$274 nightly

Sep 2 - Sep 3

Total with taxes and fees

18. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Bryan

$183 nightly

Aug 31 - Sep 1

Total with taxes and fees

2 restaurants; breakfast, lunch, and dinner served

19. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Luis

$231 nightly

Aug 30 - Aug 31

Total with taxes and fees

20. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Evelyn

$213 nightly

Aug 9 - Aug 10

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 acclaimed theater scene in this vibrant 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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A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Top South Side Hotel Reviews

Carlton Inn Midway

8/10 Good

"Room clean and air worked. Lots of plugs. Shuttle to airport nice, clean and on time. Didn’t eat breakfast there so no comment on that. Staff very friendly. Bathroom small but appears recently updated and nice. Overall room very dated but fit price for the area. Cons: no phone to contact front desk/ one set of sheets stained / pillows very hard/ WiFi only worked for one person/ holes in walls in several places/ no hot water in shower/ cheap towels / only 3 hangers. "

Skylark Motel

10/10 Excellent

"Very reasonably priced, great location. Short drive to both Rate Field and Wriggly Field. And just a couple of miles from Midway Airport. Staff was exceptional, especially the female manager who saved our stay by correcting an error not of the hotel's doing but of the booking agent. She was upfront, honest and very personable."

Best Western Inn & Suites - Midway Airport

10/10 Excellent

"The name "Midway Airport" is misleading, as this hotel doesn't really have anything to do with the airport. The parking lot is also quite small. I do want to recognize the young man working the front desk on the night shift. He had outstanding hospitality skill, he was professional, welcoming, and genuinely friendly. He made the best impression during our stay and deserves recognition for his excellent customer service. I wish I had gotten his name so I could name him. His hospitality skills deserves to be at a top tier hotel. Unfortunately, the hotel itself was very disappointing. It was under construction, but this was never disclosed when I booked. Had I known, I would have chosen a different hotel, especially considering it wasn't inexpensive. The hallways were covered in plastic sheeting, there was plaster work in progress, dust in the air, and a noticeable construction smell throughout the property. There were also many large dogs in the hotel, which added to the uncomfortable atmosphere. Overall, I did not feel like I was staying at a quality hotel. The condition of the property completely ruined what was supposed to be a special mother-daughter getaway. It was not worth the price I paid, and I left feeling disappointed. I contacted Expedia right away asking to be moved to another hotel as I felt deceived but it didn’t happen. I would not recommend this hotel."