South Chicago Vacations from $250
Book a Hotel + Flight or Car together to unlock savings
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 - River North
Downtown Chicago
Save 100% on your flight
Price was $1,418, price is now $831 per person
$831
per person
Nov 25 - Dec 2
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
The building and the apartment was excellent
Reviewed on Oct 2, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $802, price is now $488 per person
$488
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Everything was amazing. From the room itself, the breakfast and the staff
Reviewed on Oct 2, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $810, price is now $532 per person
$532
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Clean room. Great staff
Reviewed on Oct 2, 2025
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
5 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.
Discover the most popular places to visit in South Chicago
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Chicago Sightseeing River and Lake Cruise
$45
per adult
100% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Hotels near Chicago 83rd Street Station
- Hotels near Chicago 87th Street Station
- Hotels near Chicago 79th Street Station
- Hotels near Chicago 93rd Street Station
- Hotels near Calumet Heights
- 4 Star Hotels in Calumet Heights
- 3 Star Hotels in Calumet Heights
- Guest Houses in Chicago Windsor Park Station
- Hotels near Chicago Windsor Park Station
- Hotels near South Shore
- Motel 6 Hotels in South Shore
- Extended Stay America Hotels in South Shore
- 5 Star Hotels in South Shore
- Hotels near Merrionette Manor
- Hotels near Jeffrey Manor
- 3 Star Hotels in Jeffrey Manor
- Hotels near Chicago South Shore Station
- Hotels near Bronzeville Children's Museum
- Hotels near Avalon Park
- 5 Star Hotels in Avalon Park
- Hyatt Hotels in Avalon Park
- Hotels near South Shore Golf Course
- Hotels near Calumet Park
- Hotels near Chicago Bryn Mawr Station
- Hotels near Chicago Stony Island Station
- Hotels near Chicago 79th Street Station
- Hotels near Chicago 83rd Street Station
- Hotels near Essex
- Gay friendly Hotels in Essex
- Hilton Hotels in Essex
- Hotels near Burnside
- Hotels near ETA Creative Arts Foundation
- Hotels near Jackson Park Highlands
- 5 Star Hotels in Jackson Park Highlands
- Hotels near Chicago 87th Street Station
- B&B in Chicago Stony Island Station
- Hotels near Chicago 75th Street Station
- Hotels near Chicago 91st Street Station
- Hotels near East Side
- La Quinta Inn & Suites Hotels in East Side
- Hotels near Chicago 95th Street Station
- Hotels near Jackson Park
- B&B in North Pullman
- Hotels near Pullman
- 5 Star Hotels in Pullman
- Hyatt Hotels in Pullman
- 4 Star Hotels in Pullman
- Hotels near Dauphin Park
- Hotels near South Deering
- Hotels near Chatham
- 5 Star Hotels in Chatham
- 4 Star Hotels in Chatham
- Hotels near Chicago 63rd Street Station
- Hotels near Oak Woods Cemetery
- 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
- Chicago 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
- Car rentals near South Shore
- 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.