South Side Vacations from $489
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Save 100% on your flight
Price was $739, price is now $489 per person
$489
per person
Jul 18 - Jul 21
found 7 hours ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
9.4/10 Exceptional! (494 reviews)
Great team of staff. I requested to check in early and front desk staff were so sweet and allowed me to have my room 3 hours before 3pm. Amazing hotel. Nice breakfast. It was not fancy but the quality was exellent. Super close to the Met train station. All and all. I was very pleased.
Reviewed on May 16, 2026
JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,027, price is now $673 per person
$673
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities
Reviewed on May 3, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,262, price is now $854 per person
$854
per person
Aug 13 - Aug 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,357, price is now $937 per person
$937
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment!
The rooftop bar was very pleasant place to sit and chill.
Strongly recommended!!!
Reviewed on May 26, 2026
Holiday Inn Express & Suites Lockport by IHG
Save 100% on your flight
Price was $2,003, price is now $1,388 per person
$1,388
per person
Jul 29 - Aug 4
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (443 reviews)
Clean, quiet room. Good quality breakfast.
Reviewed on May 14, 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.
Discover the most popular places to visit in South Side
University of Chicago
Enjoy the collegiate vibe when you visit University of Chicago, during your travels in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
Griffin Museum of Science and Industry
This large, interactive museum contains a coal mine and World War II submarine among its many attractions.
Jackson Park
Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene.
What to do in South Side
Skydeck - Willis Tower Admission
$44
per adult
96% of travellers recommend
South Side Hotel Deals
Jaslin Hotel
261 West Cermak Rd Chicago IL
9/10 Wonderful! (1,216 reviews)
"This was such a great hotel, I was here for a short stay with a friend and the staff was so nice and chill and the room was great! Everything super simple and easy thank you Jaslin Hotel if I’m ever in Chinatown again you will be seeing me"
Reviewed on May 26, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
$164 nightly
The price is $191 total per night from May 27 to May 28
$191 total
May 27 - May 28
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
"Nice place and good price"
Reviewed on May 23, 2026
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave Chicago IL
Fully refundable
$159 nightly
The price is $187 total per night from May 27 to May 28
$187 total
May 27 - May 28
Total with taxes and fees
9/10 Wonderful! (1,333 reviews)
"good staff"
Reviewed on May 26, 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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- Chicago Vacations
- Obama's House
- Kam Synagogue
- 4944 S Woodlawn Ave
- Griffin 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
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- 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.
