South Side Vacations from $502
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $737, price is now $502 per person
$502
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
The hotel did not clean our room until we contacted the staff of when contacted took remain uncleared . It also seemed like some of the valet employees were either new or there was a lack of communication, because our vehicle was delayed several times—even beyond the estimated pickup time. Overall, there is definitely room for improvement in both housekeeping and valet service.
Reviewed on Jul 6, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,524, price is now $1,602 per person
$1,602
per person
Sep 14 - Sep 17
found 20 hours 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
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,210, price is now $819 per person
$819
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location.
The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.
Reviewed on Jul 6, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $932, price is now $640 per person
$640
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Service was poor - over a 10-day stay, my room was not made-up when I returned on some days (after 5 PM on two days and after 8 PM on another). I had to call the front desk and request housekeeping. The front desk was not particularly friendly. The room was fine, but next time I will look to stay elsewhere in Fulton Market.
Reviewed on Jul 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,318, price is now $910 per person
$910
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Clean and beautiful location. Breakfast was the best part . Bar and tv in lobby was great
Reviewed on Jul 6, 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 12 to Jul 13
$171 total
Jul 12 - Jul 13
Total with taxes and fees
8.2/10 Very Good! (1,018 reviews)
"Great staff, clean rooms, and close to Midway. Be aware that breakfast and parking cost extra ($17 for breakfast, $23 for parking)"
Reviewed on Jul 6, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
