South Chicago Vacations from $565
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Your South Chicago Vacation
South Chicago is calling! Whatever type of getaway you're organizing, get ready to discover the best of this neighborhood with a South Chicago vacation package. When it's time to get out and explore, you'll find lots of big-name attractions nearby including Calumet Park, Calumet Beach and Munson Beach. Visit one, two (or even all!) during your trip to South Chicago. Expedia is here to put your plans into action. Book your ideal South Chicago vacation today.
The Latest South Chicago 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 $911, price is now $565 per person
$565
per person
May 22 - May 25
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet
Reviewed on Feb 22, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,094, price is now $613 per person
$613
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on Mar 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,266, price is now $755 per person
$755
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,595 reviews)
Coffee in the room and just stunning views
Reviewed on Mar 4, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $1,272, price is now $808 per person
$808
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
We loved are stay at the Thompson hotel. It's very clean, and is close to our favorite shops and restaurants.
Reviewed on Mar 2, 2026
Where to stay in South Chicago
Find the best South Chicago areas and neighborhoods for the activities you enjoy most. Learn more about South Chicago
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
South Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $118 total per night from Mar 8 to Mar 9
$118 total
Mar 8 - Mar 9
Total with taxes and fees
8/10 Very Good! (9,914 reviews)
Very pleased with our room; very clean, obviously "moderned" up a little for an old hotel. Main lobby beaytufu
Reviewed on Mar 4, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $159 total per night from Mar 15 to Mar 16
$159 total
Mar 15 - Mar 16
Total with taxes and fees
9.4/10 Exceptional! (3,455 reviews)
Overall the experience was amazing
Reviewed on Mar 5, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$122 nightly
The price is $143 total per night from Mar 23 to Mar 24
$143 total
Mar 23 - Mar 24
Total with taxes and fees
8.6/10 Excellent! (5,714 reviews)
The pool was down literally out of order our entire stay except for the check out dat abs check out is before 11am. We were super bummed and kids were disappointed. 😢
Reviewed on Mar 4, 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.
Discover the most popular places to visit in South Chicago
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Explore a world of travel with Expedia
- Chicago Hotels
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- Hotels near Chicago 63rd Street Station
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- Guest Houses in Chicago 63rd Street Station
- Hotels near Garden of the Phoenix
- Hotels near A. Philip Randolph Pullman Porter Museum
- Visit Calumet Heights
- Bronzeville Children's Museum
- Visit South Shore
- Visit Merrionette Manor
- Visit Jeffrey Manor
- Visit Avalon Park
- Eta Creative Arts Foundation
- Griffin Museum of Science and Industry
- Visit Essex
- Visit Burnside
- Visit Jackson Park Highlands
- Jackson Park
- Visit East Side
- Visit Chatham Fields
- Visit Pullman
- Visit Dauphin Park
- Visit South Deering
- Visit Chatham
- Garden of the Phoenix
- A. Philip Randolph Pullman Porter Museum
- Paul H. Douglas Nature Sanctuary
- Robie House
- Rockefeller Memorial Chapel
- Lorado Taft's Midway Studios
- Car rentals near Chicago
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- First Car Rental Rental Cars in South Shore
- Enterprise Rental Cars in South Shore
- Car rentals near Jeffrey Manor
- Car rentals near Avalon Park
- Car rentals near Calumet Park
- Car rentals near Essex
- Car rentals near Jackson Park Highlands
- Car rentals near East Side
- Enterprise Rental Cars in East Side
- Car rentals near Chatham Fields
- Car rentals near Jackson Park
- Car rentals near Pullman
- Car rentals near Dauphin Park
- Car rentals near Chatham
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.