South Side Holidays from AU$2,646
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The Latest South Side Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
AU$2,646
per person
25 Oct - 1 Nov
found 9 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
8.2/10 Very good! (2,992 reviews)
Room is small, but it is appropriate for someone like me who solo travels. I had a good time!
Reviewed on 2 Sept 2026
Our guide on 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 South Wentworth Street and Chinese American Museum of Chicago. 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
1 out of top 10 points of interest in this area
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.
South Side Holiday
South Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Top Sights | Jackson Park, Washington Park and Abbott Park |
Our pick of the best South Side Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
AU$238
23 Sept - 24 Sept
includes taxes & fees
7/10 Good! (1,007 reviews)
"The hotel was really nice and the rooms are clean and nice looking. Also only a 5-7 minutes walk from the Metra station and the bus station that gets you downtown pretty easily. Overall it was a really nice and located in a safe neighbourhood. The only negative about this place was that the wi-fi ..."
Reviewed on 2 Sept 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
AU$229
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (1,001 reviews)
"Staff"
Reviewed on 2 Sept 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
AU$217
29 Sept - 30 Sept
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 acclaimed art galleries 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 theatre scene and fascinating museums in this vibrant area.
Griffin Museum of Science and Industry
9.2/10 (1,796 reviews)
A large museum close to downtown Chicago with plenty for all ages to see and do, with exhibits including a coal mine and World War II submarine.
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 fascinating museums and acclaimed art galleries 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 galleries.
Barack Obama Residence
You can find out about the history of Chicago with a stop at Barack Obama Residence. Stroll along the beautiful beaches 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.
Ida B Wells House
You can find out about the history of Chicago with a visit to Ida B Wells House. Amble around this vibrant area's lakeside or experience its fascinating museums.
What to do in South Side
Wendella's 90-min Chicago River Architecture Tour
AU$56
per adult
94% of travellers recommend
Chicago White Sox Baseball Game at Guaranteed Rate Field
AU$55
per adult
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 AU$2,646. 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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- Abbott Park
- Apache Park
- Art Institute of Chicago
- Buckingham Fountain
- Visit Armour Square
- Visit Canaryville
- Visit Downtown Chicago
- Visit Gold Coast
- Visit Grand Boulevard
- Visit Jackson Park Highlands
- Visit Magnificent Mile
- Visit River North
- Chicago Riverwalk
- Visit South Loop
- Visit The Loop
- Visit West Loop
- Chicago Holidays
- Visit Chicago
- Cloud Gate
- Downtown Chicago Holidays
- Elk Grove Village Holidays
- Frank Lloyd Wright Historic District
- Garfield Park Conservatory
- Gold Coast Holidays
- Golf Holidays
- Grant Park
- Griffin Museum of Science and Industry
- Kathy Osterman Beach
- Legoland® Discovery Center
- Lincoln Hall
- Lincoln Park Zoo
- Lombard Holidays
- Millennium Park
- Montrose Beach
- Navy Pier
- Norma Holidays
- Oak Street Beach
- Pullman Holidays
- Six Flags Great America
- University of Illinois Chicago
- Waukegan BMX Track
- Willis Tower
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
