South Side Vacations from $522

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The Latest South Side vacation packages

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Four Seasons Hotel Chicago
Level Chicago - River North
Hotel Riu Plaza Chicago
Level Chicago – Old Town
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South Side Hotel Deals

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is $171 total per night from Jul 12 to Jul 13
$171 total
per night
Jul 12 - Jul 13
8.2/10 Very Good! (1,019 reviews)
"Guest services was very rude and when I mentioned my vision impairment and asked for help with parking, I was refused help. I was told that it was a third-party source and that they did not have any information on the app in the morning. I talked to the GM, who was very helpful and told me that I ..."

Reviewed on Jul 7, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is $113 total per night from Aug 3 to Aug 4
$113 total
per night
Aug 3 - Aug 4
7.4/10 Good! (390 reviews)
"If you want a cheap and affordable room. Motel 6 is the best option to go with. Clean room, helpful staff. Only downside was the ice machine was out of order for some reason."

Reviewed on Jul 5, 2026

Motel 6 - Chicago, IL
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
The price is $157 total per night from Jul 8 to Jul 9
$157 total
per night
Jul 8 - Jul 9
9/10 Wonderful! (1,244 reviews)
"Property was clean and staff was helpful. Had a great stay!"

Reviewed on Jul 6, 2026

Jaslin Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best South Side Vacation Packages

South Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.