South Side Vacations from $187
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $355 per person
$355
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on Dec 14, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $545, price is now $321 per person
$321
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
The view of our king room was beautiful. However The bathroom had blue stains on the wall, the bathroom door looked as it was kicked in, and the seating area couch by the window had stains.
Reviewed on Dec 15, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $582, price is now $347 per person
$347
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $315, price is now $189 per person
$189
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on Dec 8, 2025
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
4 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.
Discover the most popular places to visit in South Side
University of Chicago
4.5/5(1,167 reviews)
Enjoy the collegiate vibe when you visit University of Chicago, during your travels in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Griffin Museum of Science and Industry
4.5/5(1,381 reviews)
This large, interactive museum contains a coal mine and World War II submarine among its many attractions.
Illinois Institute of Technology
3.5/5(4 reviews)
Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the fascinating museums and acclaimed theater scene in this vibrant area.
What to do in South Side
Chicago Bulls Basketball Game at United Center
$80
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
South Side Hotel Deals
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave Chicago IL
Fully refundable
$112 nightly
The price is $132 total per night from Dec 21 to Dec 22
$132 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (1,233 reviews)
Very friendly staff, prompt check in at the rate I was quoted. Facilities were clean and well supplied, somewhat faded, but I’m sure they do a very high volume at this hotel so not unexpected.
Reviewed on Dec 11, 2025
SpringHill Suites by Marriott Chicago Chinatown
2357 S WENTWORTH AVE Chicago IL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $131 total per night from Jan 1 to Jan 2
$131 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
From the moment we checked in, this was one of my best hotel experiences ever. I'm a Chicago native leaving abroad, and my partner and I would definitely stay here again. Love the neighborhood and this hotel is a great addition.
Reviewed on Dec 9, 2025
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $94 total per night from Dec 16 to Dec 17
$94 total
Dec 16 - Dec 17
Total with taxes and fees
6.8/10 (200 reviews)
Great stay
Reviewed on Dec 4, 2025
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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- Chicago Vacations
- Obama's House
- KAM Synagogue
- 4944 S Woodlawn Ave
- Chicago Museum of Science and Industry
- Elijah Muhammad House
- Visit Washington Park Court
- Smart Museum of Art
- Muddy Waters’ House
- DuSable Museum of African-American History
- Hyde Park Vacations
- Hyde Park Hair Salon
- Robie House
- Visit Grand Boulevard
- University of Chicago
- Visit Kenwood
- Midway Plaisance
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- Rockefeller Memorial Chapel
- Car rentals near Chicago
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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.