
South Side Vacations from $190
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The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.



The Emily Hotel
Downtown Chicago
Price was $968, price is now $481 per person
$481
per person
Feb 13 - Feb 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) 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

Level Chicago – Old Town
Downtown Chicago
Price was $692, price is now $348 per person
$348
per person
Feb 13 - Feb 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was $687, price is now $347 per person
$347
per person
Feb 13 - Feb 17
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on Nov 26, 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 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! (1,212 reviews)
Holiday Inn was clean & convenient. The shuttle was a nice plus. I thought the price for one night was a bit high. My flight was canceled & I picked The Holiday Inn because I always enjoy staying there.
Reviewed on Dec 1, 2025

SpringHill Suites by Marriott Chicago Chinatown
2357 S WENTWORTH AVE Chicago IL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $139 total per night from Dec 7 to Dec 8
$139 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 4 to Dec 5
$94 total
Dec 4 - Dec 5
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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- 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
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- Hyde Park Hair Salon
- Robie House
- Visit Grand Boulevard
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- Rockefeller Memorial Chapel
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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.























