South Chicago Vacations from $212
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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was $452, price is now $212 per person
$212
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
Food price was high but everything was fine
Reviewed on Oct 4, 2025
Level Chicago – Old Town
Downtown Chicago
Price was $634, price is now $325 per person
$325
per person
Jan 7 - Jan 11
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue.
However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).
Reviewed on Oct 22, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,674, price is now $908 per person
$908
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
I didn't like the two occasions I used the men's bathroom on the first floor (lobby) because on both occasions, the single toilet was being used. Would be great if a second toilet was installed since there is plenty of room to do so.
Loyal Customer.
Dimitri R
Reviewed on Oct 24, 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.
South Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Nov 24 to Nov 25
$136 total
Nov 24 - Nov 25
Total with taxes and fees
7.8/10 Good! (9,567 reviews)
LOVED the room and the view was spectacular! The location could not have been any more convenient. Lobby was beautiful. Our room had a separate living room with bay windows looking out over Lake Michigan and the city. The bedroom was fantastic with a comfortable bed and pillows. We slept so well. ...
Reviewed on Oct 24, 2025
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
$120 nightly
The price is $141 total per night from Nov 24 to Nov 25
$141 total
Nov 24 - Nov 25
Total with taxes and fees
8.8/10 Excellent! (1,958 reviews)
The room was very nice and clean. The bed was really comfortable. Staff was very helpful and the restaurant was excellent. Definitely would stay here again.
Reviewed on Oct 20, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Nov 16 to Nov 17
$129 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,145 reviews)
Hotel was everything i needed for a work trip
Reviewed on Oct 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.
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
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
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.