South Side Vacations from $983
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,524, price is now $983 per person
$983
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The property was amazing including the buffet breakfast.
Reviewed on Jul 6, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,557, price is now $997 per person
$997
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This was a very clean and nice hotel. I enjoyed the room.
Reviewed on Jul 6, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,513, price is now $986 per person
$986
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
The staff did not explain that room cleaning was available only upon request. For the breakfast specialty coffee you had to wait for the front desk staff to be available.
Reviewed on Jul 6, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,562, price is now $1,682 per person
$1,682
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!
Reviewed on Jul 6, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,635, price is now $1,079 per person
$1,079
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Great boutique hotel in a great location! Definitely will stay here again when visiting Chicago.
Reviewed on Jul 5, 2026
Where to stay in South Side
Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
Hyde Park
3 out of top 10 points of interest in this area
4.5/5(136 area reviews)
Art and history abound in this architecturally impressive and leafy neighborhood between Washington Park and the shores of Lake Michigan.
Stay near popular South Side attractions
What to do in South Side
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
South Side Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $171 total per night from Jul 9 to Jul 10
$171 total
Jul 9 - Jul 10
Total with taxes and fees
8.2/10 Very Good! (1,016 reviews)
"Clean, good neighborhood close to CTa Orange Line, staff was helpful, courteous property was well maintained air conditioning was on point very cold for the extreme heat"
Reviewed on Jul 5, 2026
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $113 total per night from Aug 3 to Aug 4
$113 total
Aug 3 - Aug 4
Total with taxes and fees
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
Jaslin Hotel
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $157 total per night from Jul 7 to Jul 8
$157 total
Jul 7 - Jul 8
Total with taxes and fees
9/10 Wonderful! (1,244 reviews)
"Property was clean and staff was helpful. Had a great stay!"
Reviewed on Jul 6, 2026
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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- Michigan Avenue Bridge
- Downtown Chicago Vacations
- Chicago Symphony Orchestra
- University of Illinois Chicago
- Rookery
- Grant Park
- Sr Crown Hall
- Wrigley Field
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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.
