TOP Hotels with Air Conditioning in South Side, IL for 2026

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Check availability on South Side Hotels with Air Conditioning

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Our top choices for South Side hotels with air conditioning

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Julie

includes taxes & fees

9 Aug - 10 Aug

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Anna

includes taxes & fees

27 Jul - 28 Jul

2 restaurants; breakfast, lunch and dinner served

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Sophie

includes taxes & fees

9 Aug - 10 Aug

Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Danny

includes taxes & fees

12 Aug - 13 Aug

Congress Plaza Hotel

Downtown Chicago

Ashley

includes taxes & fees

10 Aug - 11 Aug

Palmer House a Hilton Hotel

Downtown Chicago

Britney Q

includes taxes & fees

7 Aug - 8 Aug

Silversmith Hotel Chicago Downtown

Downtown Chicago

Taylor

includes taxes & fees

9 Aug - 10 Aug

Freehand Chicago

Downtown Chicago

Traci

includes taxes & fees

10 Aug - 11 Aug

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Top South Side Hotel Reviews

Chicago Lake Shore Hotel

10/10 Excellent

"The room was clean. The facility wasn't offer much. The wifi was very weak, and the feeling was we are staying at the cheap motel, not hotel."

Carlton Inn Midway

8/10 Good

"It’s not the best and it’s not the worst. You got everything you need in the room basically. You probably won’t find parking by your room at night it gets pretty filled up, but other than that I’d probably stay here again. Just some of the stuff is old like the TV and the bath tub had like rust stains on it, but other than that everything was good."

Jaslin Hotel

10/10 Excellent

"I was so pleasantly surprised by this hotel. It was a little out of the price range I was looking for but I chose it out of convenience for my location. The photos didn’t do it justice: the hotel was very clean and comfortable. Staff was so helpful. Felt very safe as well, especially as a solo traveler. Would absolutely stay here again, and might even go out of my way to do it."

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"All in all great stay for the price. We were in town for the taste of Chicago. About 20 mins from downtown. Staff was very friendly and helpful. Rooms were clean and as described. Plenty of parking on site. The restaurant that is connected was also great. Good drinks. The lemon drops were top tier! I did not do the breakfast option. I felt it was a little pricey for hotel breakfast. (My opinion)."

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

8/10 Good

"I love the accommodations and how close it was to the airport and the shuttle schedule. The fitness room equipment was simple but effective. The breakfast was good. However, I did not like the traffic sounds I could hear at night."

Best Western Inn & Suites - Midway Airport

10/10 Excellent

"The breakfast was the best I’ve had in a while. They already had ready-made pancakes and hashbrowns. You never see that …. This young lady asked me if I needed some juice and offered to get it for me. That’s next level service. I’ll stay there every time I go to Chicago."

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Change your mind

Treat yourself

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Check availability on South Side Hotels with Air Conditioning

Our top choices for South Side hotels with air conditioning

Sable at Navy Pier Chicago, Curio Collection by Hilton

The Chicago Hotel Collection Ambassador Gold Coast