South Side Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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 hotel + flight trips 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

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 10 Dec to 11 Dec
AU$181
includes taxes & fees
10 Dec - 11 Dec
7.8/10 Good! (8,163 reviews)
"Clean updated room with great view of lake"

Reviewed on 24 Nov. 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 10 Dec to 11 Dec
AU$196
includes taxes & fees
10 Dec - 11 Dec
8.6/10 Excellent! (3,554 reviews)
"Hotel was beautiful"

Reviewed on 23 Nov. 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 10 Dec to 11 Dec
AU$186
includes taxes & fees
10 Dec - 11 Dec
8.4/10 Very Good! (3,270 reviews)
"The staff are very accommodating in allowing for early luggage drop off before check in and after checking out. Super convenient to local transit and Amtrak Chicago Union Station."

Reviewed on 24 Nov. 2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,731 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

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.

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

Abbott Park

Explore the great outdoors at Abbott Park, a lovely green space in Chicago. Discover the top-notch restaurants and acclaimed art galleries in this vibrant area.

Abbott Park

What to do in South Side

Go City - Chicago All-Inclusive Pass: 1 to 5 Day Access to 25+ Activities

Chicago Pass: Save up to 50 Percent - Includes 360 Chicago

AU$200
Per adult
78% of travellers recommend
Chicago Pass: Save up to 50 Percent - Includes 360 Chicago
Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

AU$63
Per adult
Field Museum of Natural History All-Access Pass
The Field Museum

Field Museum of Natural History Discovery Pass

AU$54
Per adult
Field Museum of Natural History Discovery Pass
See all activities in South Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.