South Side Vacations from $454
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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 $686, price is now $454 per person
$454
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (484 reviews)
Easy and secure parking. Onsite gym. Restaurants located in lobby and surrounding areas, also has continental breakfast. Room was very clean
Reviewed on May 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,684, price is now $1,046 per person
$1,046
per person
Jun 18 - Jun 22
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,991 reviews)
The room was exceptionally clean and the staff was great! The location 1/2 block from Michigan Ave. We had a wonderful stay!
Reviewed on May 9, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $884, price is now $572 per person
$572
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $725, price is now $471 per person
$471
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,096, price is now $719 per person
$719
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too
Reviewed on May 3, 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
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(1,186 reviews)
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
4.5/5(1,398 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 acclaimed theater scene and fascinating museums in this vibrant area.
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
$224 nightly
The price is $267 total per night from Jun 7 to Jun 8
$267 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (1,219 reviews)
Favourite hotel to stay at in Chicago. Great location, always a comfortable stay.
Reviewed on May 9, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
$128 nightly
The price is $149 total per night from May 10 to May 11
$149 total
May 10 - May 11
Total with taxes and fees
8.4/10 Very Good! (1,017 reviews)
Muffins were stale and bacon was burnt overall breakfast wasn’t up to par
Reviewed on May 5, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$129 nightly
The price is $151 total per night from May 10 to May 11
$151 total
May 10 - May 11
Total with taxes and fees
6.8/10 (1,004 reviews)
No hangers and no drawers for clothes
Reviewed on May 3, 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
- Visit Hyde Park
- Rockefeller Memorial Chapel
- Car rentals near Chicago
- Car rentals near 4944 S Woodlawn Ave
- Car rentals near Hyde Park
- Enterprise Rental Cars in Hyde Park
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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.
