South Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top South Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,290
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Room was very clean and spacious. Staff was very helpful when we had issues with wifi (which were resolved very fast) and issues with flight cancellations impacting our arrival. Great breakfast buffet, lots of options and convenient. Rooftop bar was beautiful! The location was perfect for walking around the city and for getting to the red line. Would definitely recommend!!
Reviewed on Aug 19, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,262
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Loved the location. Was able to park in the parking ramp, leave the car, and walk to many, many places! Room was clean, view was excellent, and choices of food/snacks was endless!
Reviewed on Aug 18, 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 Robie House.
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
1 out of top 10 points of interest in this area
Well-liked for its restaurants and churches, Bridgeport is worth a visit. Check out the variety of things to see and do like Bridgeport Art Center and Ramova Theatre, 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.
Jackson Park Highlands
The beaches and restaurants are a few reasons travelers visit Jackson Park Highlands. Want to see more of the surrounding area? Stony Island Arts Bank and South Shore Cultural Center are a few top sights nearby.
Ready to book your vacation to South Side?
South Side Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
CA $158
CA $200 total
Sep 8 - Sep 9
includes taxes & fees
8.2/10 Very good! (1,021 reviews)
"Decent property."
Reviewed on Aug 19, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
CA $227
CA $266 total
Aug 25 - Aug 26
includes taxes & fees
Jaslin Hotel
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
CA $190
CA $226 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,307 reviews)
"The room was very clean. The even staff when I checked in was friendly and helpful. When I checked out, the representative was a little cold in demeanor but she got the job done. Overall I was very pleased with my stay. It was a 15 minute walk from the arena I was going to and there’s plenty of good ..."
Reviewed on Aug 17, 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.
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 acclaimed art scene in this vibrant area.
Rate Field
8.6/10 (235 reviews)
Catch an event at Rate Field during your trip to Chicago. Experience the acclaimed theater scene and fascinating museums 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 fascinating museums and acclaimed art scene in this vibrant area.
Jackson Park
7.4/10 (9 reviews)
Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene.
Obama's House
10.0/10 (2 reviews)
Find out about the history of Chicago when you spend time at Obama's House. Amble around this vibrant area's lakeside or experience its fascinating museums.
Barack Obama Residence
You can find out about the history of Chicago when you stop by Barack Obama Residence. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.
Bridgeport Art Center
Enjoy a stop at Bridgeport Art Center, an entertaining place to visit in Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
What to do in South Side
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
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 $1,169. 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.
Explore a world of travel with Expedia
- Hotels near United Center
- Chicago Hotels
- Boutique Hotels in Chicago
- Downtown Chicago Hotels
- Hotels near Navy Pier
- Hotels near O'Hare Intl.
- Hotels with a Pool in Chicago
- Magnificent Mile Hotels
- Hotels with Free Parking in Chicago
- The Loop Hotels
- River North Hotels
- Cheap Hotels in Downtown Chicago
- Hotels near Art Institute of Chicago
- All Inclusive Resorts and in Chicago
- Marriott Hotels & Resorts in Chicago
- Hotels with Free Breakfast in Chicago
- Fulton Market Hotels
- Family Hotels in Chicago
- West Loop Hotels
- Cheap Hotels in Chicago
- Hotels near Millennium Park
- Hotels near McCormick Place
- Hotels near Michigan Avenue
- Lincoln Park Hotels
- Hotels near Soldier Field
- Hotels with Kitchenettes in Chicago
- Gold Coast Hotels
- Hotels near Wrigley Field
- Pet-Friendly Hotels in Chicago
- Hotels near Wintrust Arena
- Hotels near Midway Intl.
- Hotels with Free Airport Shuttle in Chicago
- 5 Star Hotels in Chicago
- Hotels near Grant Park
- Hostels in Chicago
- Motels in Chicago
- Flights from Buffalo (BUF) to Chicago (ORD)
- Flights from Winnipeg (YWG) to Chicago (ORD)
- Flights from Hamilton (YHM) to Chicago (ORD)
- Flights from Windsor (YQG) to Chicago (ORD)
- Flights from Halifax (YHZ) to Chicago (ORD)
- Flights from Saskatoon (YXE) to Chicago (ORD)
- Flights from Ottawa (YOW) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Flights from Midway Intl.
- Flights from Kitchener (YKF) to Chicago (ORD)
- Flights from London (YXU) to Chicago (ORD)
- Flights to Chicago
- Flights from O'Hare Intl.
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Calgary (YYC) to Chicago (ORD)
- Flights from Regina (YQR) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Toronto (YTZ) to Chicago (MDW)
- Flights from Chicago
- Flights from Montreal (YUL) to Chicago (ORD)
- Flights from Edmonton (YEG) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- 875 North Michigan Avenue
- Lincoln Park Zoo
- Montrose Beach
- Frank Lloyd Wright Historic District
- Golf Vacations
- Visit Chicago
- Wrigley Field
- Unity Temple
- Garfield Park Conservatory
- Visit Downtown Chicago
- Marina City
- Ernest Hemingway Museum and House
- Visit Magnificent Mile
- Chicago Riverwalk
- Phoenix Vacations
- Downtown Chicago Vacations
- International Museum of Surgical Science
- Griffin Museum of Science and Industry
- Millennium Park
- Buckingham Fountain
- Chicago Vacations
- Art Institute of Chicago
- Navy Pier
- Water Tower Place
- Robie House
- 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.
