South Side Vacations

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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
4.5/5(136 area reviews)

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

Find the Best South Side Vacation Packages

South Side Hotel Deals

Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
Fully refundable
The price is ₩161,317 per night from Sep 2 to Sep 3
₩161,317
₩189,343 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,101 reviews)
"There website and Expedia show check-in time of 3pm. We weren't allowed to check-in until 4pm and hed to wait in the lobby with many people who were also led to believe it was 3pm....other than that it was a wonderful hotel. I would definitely stay there again if visiting Chicago."

Reviewed on Jul 31, 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 ₩223,705 per night from Aug 24 to Aug 25
₩223,705
₩262,608 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (958 reviews)
"Breakfast was great. Rooms clean and well kept. Friendly staff."

Reviewed on Jul 30, 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 ₩93,775 per night from Sep 1 to Sep 2
₩93,775
₩110,073 total
Sep 1 - Sep 2
includes taxes & fees
6.2/10 (50 reviews)
"The place was cool."

Reviewed on Jul 31, 2025

Motel 6 - Chicago, IL
See all 461 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.

Discover the most popular places to visit in South Side

Robie House

University of Chicago

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 scene in this vibrant area.

University of Chicago
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Frequently asked questions

How much does a South Side vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing 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 vacation 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 favorites. 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 vacation?
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 vacation 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 vacation 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 vacation 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.