South Side Vacations from $265
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Save 100% on your flight
Price was $491, price is now $265 per person
$265
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (MDW)
9.4/10 Exceptional! (160 reviews)
Overall good but never clraned the room.
Reviewed on Nov 29, 2025
Level Chicago Fulton Market
Downtown Chicago
Price was $1,117, price is now $552 per person
$552
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.
Reviewed on Nov 25, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $923, price is now $520 per person
$520
per person
Feb 12 - Feb 15
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was $2,366, price is now $1,339 per person
$1,339
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The staff was amazing. Will be making a return stay.
Reviewed on Nov 30, 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
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
This large, interactive museum contains a coal mine and World War II submarine among its many attractions.
Illinois Institute of Technology
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
Chicago Bulls Basketball Game at United Center
$98
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$45
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
$123 nightly
The price is $145 total per night from Dec 8 to Dec 9
$145 total
Dec 8 - Dec 9
Total with taxes and fees
8.8/10 Excellent! (1,197 reviews)
It served its purpose for me. That’s all I needed and I was satisfied.
Reviewed on Nov 19, 2025
SpringHill Suites by Marriott Chicago Chinatown
2357 S WENTWORTH AVE Chicago IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $159 total per night from Dec 7 to Dec 8
$159 total
Dec 7 - Dec 8
Total with taxes and fees
9.4/10 Exceptional! (1,004 reviews)
The staff were friendly and helpful. The room was very clean. Breakfast was good.
Reviewed on Nov 13, 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 2 to Dec 3
$94 total
Dec 2 - Dec 3
Total with taxes and fees
6.8/10 (186 reviews)
Grest
Reviewed on Nov 25, 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
- Visit Hyde Park
- 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.