South Side Holidays

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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
Chicago Museum of Science and Industry

Hyde Park

4 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.

Find hotels in Hyde Park

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

Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
Fully refundable
The price is AU$215 per night from 17 Aug to 18 Aug
AU$215
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,095 reviews)
"Would have loved a pool."

Reviewed on 28 Jul. 2025

Jaslin Hotel
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 out of 5
2357 S WENTWORTH AVE, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$290 per night from 24 Aug to 25 Aug
AU$290
24 Aug - 25 Aug
includes taxes & fees
9.4/10 Exceptional! (955 reviews)
"This is a really great place in an excellent area. We ate some authentic cuisine and took an Uber to a concert. Everything was great. Easy check in, welcoming staff, and outstanding location."

Reviewed on 28 Jul. 2025

SpringHill Suites by Marriott Chicago Chinatown
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$123 per night from 31 Aug to 1 Sept
AU$123
31 Aug - 1 Sept
includes taxes & fees
6/10 (49 reviews)
"I appreciate all the people that work at this motel 6! They are polite and always willing to help with reservations. I also have a service animal and it's been so peaceful to stay there."

Reviewed on 17 Jul. 2025

Motel 6 - Chicago, IL
See all 448 properties in South Side
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in South Side

Chicago Museum of Science and Industry

Chicago Museum of Science and Industry

4.5/5(11 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.

Chicago Museum of Science and Industry
Jackson Park

Jackson Park

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.

Jackson Park
Robie House

Robie House

Witness the simple beauty of Frank Lloyd Wright’s designs in a Chicago house that epitomizes a popular American style of architecture.

Robie House

What to do in South Side

River tour boat in Chicago

Architecture River Tour

AU$64
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

AU$46
per adult
92% of travellers recommend
Skyline Lake Tour
Chicago White Sox Baseball Game at Guaranteed Rate Field

Chicago White Sox Baseball Game at Guaranteed Rate Field

AU$31
per adult
Chicago White Sox Baseball Game at Guaranteed Rate Field
See all activities 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 . 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.