South Side Vacation Packages
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Top South Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,184
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.
Reviewed on Oct 7, 2026
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
3 out of top 10 points of interest in this area
Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Griffin Museum of Science and Industry.
Chinatown
If you're spending time in Chinatown, you might enjoy attractions like Chinese American Museum of Chicago and On Leong Building. You might also enjoy the neighborhood's ample dining options before hopping on the metro at Cermak-Chinatown Station to see more of the city.
Bridgeport
Well-liked for its restaurants and churches, Bridgeport is worth a visit. Check out the variety of things to see and do like Zhou B Art Center and Bridgeport Art Center, and jump on the metro at Halsted Station (Orange Line) to get around the city.
Bronzeville
Travelers choose Bronzeville for its abundant dining options. Hop aboard the metro at 35th-Bronzeville-IIT Station or Indiana Station and check out top sights like Lake Michigan.
Woodlawn
2 out of top 10 points of interest in this area
Woodlawn is well-liked for its beaches and restaurants. If you're hoping to get in some sightseeing, Lake Michigan and Obama Presidential Center are top spots, and you can jump on the metro at Cottage Grove Station or King Drive Station to get around.
Ready to book your vacation to South Side?
South Side Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
CA $192
CA $225 total
Nov 1 - Nov 2
includes taxes & fees
7/10 Good! (1,004 reviews)
"Definitely a motel vibe, no elevator. Nice staff and clean rooms."
Reviewed on Oct 5, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
CA $198
CA $246 total
Oct 25 - Oct 26
includes taxes & fees
8.2/10 Very good! (1,011 reviews)
"clean room."
Reviewed on Oct 6, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
CA $203
CA $241 total
Oct 25 - Oct 26
includes taxes & fees
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.
Stay near popular South Side attractions
University of Chicago
8.6/10 (3,689 reviews)
Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
Rate Field
8.6/10 (235 reviews)
Catch an event at Rate Field during your trip to Chicago. Experience the entertainment choices and acclaimed theater scene in this vibrant area.
Griffin Museum of Science and Industry
9.2/10 (1,796 reviews)
This large, interactive museum contains a coal mine and World War II submarine among its many attractions.
Illinois Institute of Technology
7.0/10 (4 reviews)
Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.
Barack Obama Residence
You can find out about the history of Chicago when you stop by Barack Obama Residence. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Rainbow Beach
Why not spend a lazy afternoon at Rainbow Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
Obama Presidential Center
You can spend an afternoon exploring the galleries in Obama Presidential Center during your trip to Chicago. Wander the beaches and gardens while you're in the area.
Wabash Ave YMCA
You can find out about the history of Chicago when you stop by Wabash Ave YMCA. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
What to do in South Side
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a South Side vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in South Side from just CA $1,184. And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to South Side?
Book everything in the one place with our South Side vacation packages. You'll find deals on flights, hotels and more that'll keep your pocket happy and your adventurous side busy. And, with more than 550 air carriers and 1,000,000 hotels throughout the world to pick from, you'll have the flexibility to mix and match all you want.
What are the top hotels in South Side?
When it comes to properties in Carville, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are a couple of favorites. If you're considering heading to Chatham Fields, The Whitehall Hotel and Hyatt Regency Chicago are waiting to welcome you.
How far in advance should I book my South Side vacation?
While not all airlines advertise ticket prices early, it's usually possible to look up international flights on Expedia up to a year in advance. This is the time you can bag some incredible deals. If you're purchasing tickets last minute, there's a chance you could get lucky. Sometimes the lowest prices become available a few weeks prior to departure.
What does an Expedia South Side travel package include?
Expedia has everything you need to book your South Side escape, but what your package looks like is up to you. Choose from a combination of rental cars, hotels and flights. Searching for some activities to keep you busy? Once you've made your booking, you can add them on too. Whatever your style or budget, there's a package deal to suit your needs.
What should I know before booking a South Side travel package?
Discover deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we're a one-stop shop for all of them. You'll save precious cash just for combining your bookings. Whether you're embarking on a ski trip or relaxing on a sunny beach, your perfect getaway is only clicks away.
Can I choose my airline with a South Side Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to choose from all over the world. With so many choices, finding the right carrier to bring you to South Side will be a snap.
If I'm not able to travel, can I cancel my South Side vacation package?
You can. We get that even the best-laid plans can go awry, so we're here to help if you have to make changes to your South Side vacation package. It may be possible to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.
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- 875 North Michigan Avenue
- Lincoln Park Zoo
- Montrose Beach
- Frank Lloyd Wright Historic District
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- Visit Chicago
- Wrigley Field
- Unity Temple
- Garfield Park Conservatory
- Visit Downtown Chicago
- Marina City
- Ernest Hemingway Museum and House
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- Chicago Riverwalk
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- International Museum of Surgical Science
- Griffin Museum of Science and Industry
- Millennium Park
- Buckingham Fountain
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- Art Institute of Chicago
- Navy Pier
- Water Tower Place
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- Ann and Robert H. Lurie Children's Hospital
- Lakeview Vacations
- Grant Park
- United Center
- Visit The Loop
- Willis Tower
- The Loop Vacations
- Northwestern University
- Chicago Theatre
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
