South Side Holidays
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Top Flight + Hotel Deals in South Side
Price found within the past 48 hours. Click for updated prices.
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 neighbourhood'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 Bridgeport Art Center and Ramova Theatre, and jump on the metro at Halsted Station (Orange Line) to get around the city.
Bronzeville
Consider exploring the abundant dining options in Bronzeville. If sightseeing is on the list, Lake Michigan is a top attraction. Hop on the metro at 35th-Bronzeville-IIT Station or Indiana Station to see more of the area.
Douglas
1 out of top 10 points of interest in this area
If you're spending time in Douglas, you might enjoy attractions like Lake Michigan and Ida B Wells House. You might also enjoy the neighbourhood's ample dining options before hopping on the metro at 35th-Bronzeville-IIT Station to see more of the city.
Top hotels in South Side
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
€172
20 Sept - 21 Sept
includes taxes & fees
7/10 Good! (1,005 reviews)
"Great location. Very clean-looks refurbished. The staff is amazing-very helpful & they try to help you have a good experience!"
Reviewed on 15 Sept 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
€163
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (1,001 reviews)
"Na"
Reviewed on 16 Sept 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
€176
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (1,369 reviews)
"Room cleaned and well maintained"
Reviewed on 16 Sept 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 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 theatre 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)
Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed art galleries and fascinating museums 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 fascinating museums.
Barack Obama Residence
You can find out about the history of Chicago with a stop at Barack Obama Residence. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.
Obama Presidential Center
You can spend an afternoon browsing the exhibits at Obama Presidential Center in Chicago. Wander the beaches and gardens while you're in the area.
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.
What to do in South Side
Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend
Frequently asked questions
How much does a South Side holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in South Side from just €1,059. 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 holiday 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 favourites. 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 holiday?
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 holiday 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 holiday 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 holiday 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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- Ann and Robert H. Lurie Children's Hospital
- Aon Center
- Art Institute of Chicago
- Buckingham Fountain
- Canalport Riverwalk Park
- Chicago Board of Trade Building
- Visit Canaryville
- Visit Chinatown
- Visit Grand Boulevard
- Chicago Museum Campus Holidays
- Chicago Place Mall
- Visit Printers Row
- Chicago Riverwalk
- Visit South Commons
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- Cloud Gate
- Credit Union 1 Arena
- Crown Fountain
- Daley Plaza
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- Lake Meadows Park
- Lincoln Park Zoo
- Michigan Avenue
- Millennium Park
- Navy Pier
- Prentice Women's Hospital
- Robie House
- Second Franklin Building
- Smith Museum of Stained Glass Windows
- University of Illinois Chicago
- Water Tower Place
- Willis Tower
- Wrigley Building
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
