South Side Holidays from NZ$1,333
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The Latest South Side Holiday Deals
Price found within the past 48 hours. Click for updated prices.
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 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.
South Side Holiday
Our pick of the best South Side Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
NZ$347
23 Sept - 24 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
NZ$329
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (1,002 reviews)
"The rooms were nice and the property was maintained well but that’s it. Customer service was so lousy to the point of almost nonexistence. They don’t offer taxi service and their airport shuttle only runs 8 hours from 7 am to 3 pm. One day they had no one to do the shuttle so I was left to my own ..."
Reviewed on 17 Sept 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
NZ$349
1 Oct - 2 Oct
includes taxes & fees
9/10 Wonderful! (1,372 reviews)
"Easy access to parking. Clean lobby. Well maintained."
Reviewed on 17 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)
Explore the campus of University of Chicago during your travels 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)
Originating in the 1930s with a mission not to be dull, immerse yourself in its breath taking, fascinating exhibits.
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
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 NZ$1,333. 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.
Explore a world of travel with Expedia
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- Grant Park
- Pritzker Pavilion
- Art Institute of Chicago
- Bridgeport Art Center
- Downtown Chicago Holidays
- Willis Tower
- Chicago Water Tower
- Copernicus Statue
- Merchandise Mart
- Mccormick Place
- Cloud Gate
- Hyde Park Hair Salon
- Robie House
- Field Museum of Natural History
- Adler Planetarium and Astronomy Museum
- Supreme Life Building
- Chicago Holidays
- Ohio Street Beach
- Crown Fountain
- Buckingham Fountain
- Navy Pier
- Harold Washington Library Center
- Water Tower Place
- Millennium Park
- Richard J. Daley Center
- Zhou B Art Center
- Wintrust Arena
- Tribune Tower
- Obama's House
- Chicago Board of Trade Building
- Visit Gage Park
- Visit South Loop
- Visit Fuller Park
- Visit Chicago
- Visit Grace Abbott Homes
- Visit Jackson Park Highlands
- Visit McKinley Park
- Visit Indian Village
- Visit Washington Park
- Visit Bronzeville
- Visit Canaryville
- Visit Greater Grand Crossing
- Visit Douglas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
