South Side Holidays

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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
3/5(1 area review)

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

Top hotels in South Side

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
2.5 out of 5
6500 S Cicero Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$173 per night from 15 Jun to 16 Jun
S$173
15 Jun - 16 Jun
includes taxes & fees
8.8/10 Excellent! (1,084 reviews)
"Good!!"

Reviewed on 5 Jun, 2025

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Jaslin Hotel
Jaslin Hotel
3 out of 5
261 West Cermak Rd, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$343 per night from 20 Jun to 21 Jun
S$343
20 Jun - 21 Jun
includes taxes & fees
8.8/10 Excellent! (1,056 reviews)
"I enjoyed my stay here. Easy check in and out. Great location. Front desk service was great also"

Reviewed on 7 Jun, 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 S$217 per night from 29 Jun to 30 Jun
S$217
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (886 reviews)
"Excellent place to stay if you are in Chicago!"

Reviewed on 6 Jun, 2025

SpringHill Suites by Marriott Chicago Chinatown
See all 417 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.

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.

Popular places to visit

Chicago Museum of Science and Industry

Chicago Museum of Science and Industry

4.5/5(23 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

What to do in South Side

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

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

S$180
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

S$53
per adult
Field Museum of Natural History All-Access Pass
Field Museum of Natural History Ticket with Self-Guided Audio Tour

Field Museum of Natural History Ticket with Self-Guided Audio Tour

S$79
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.