South Side Vacation Packages

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Top South Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,584 reviews)
Good building, a little misleading when “separate sitting area” is mentioned in the room, yet the room is still just 2 queen beds and a desk and bench all still in the same room. How is this separate if it’s in the same room? Walkable to downtown with access to everything. Clean enough

Reviewed on Jul. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Very nice amenities and food. We would come back to this property

Reviewed on Jul. 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Nice hotel with a great breakfast buffet

Reviewed on Jul. 25, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,484 reviews)
Very nice and clean place

Reviewed on Jul. 21, 2025

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(4 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

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South Side Hotel Deals

Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
Fully refundable
The price is CA $156 per night from Aug 18 to Aug 19
CA $156
CA $184 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,097 reviews)
"I enjoyed my stay at this affordable hotel in Chinatown. The staff were great, my room was clean, and good food, public transit, and parking were all in easy walking distance."

Reviewed on Jul. 24, 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 CA $232 per night from Aug 24 to Aug 25
CA $232
CA $272 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (953 reviews)
Hotel Review
"The hotel was very nice and clean. The room was very comfortable and convenient. Im a person with physical disabilities and I love how accommodating the shower set up was for me as an amputee. The shower had a bench that can fold down and up and really helped me out a lot."

Reviewed on Jul. 24, 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 CA $98 per night from Jul 27 to Jul 28
CA $98
CA $115 total
Jul 27 - Jul 28
includes taxes & fees
6/10 (41 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 Jul. 17, 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.
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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(81 reviews)

This large, interactive museum contains a coal mine and World War II submarine among its many attractions.

Chicago Museum of Science and Industry
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

Obama's House

Find out about the history of Chicago when you spend time at Obama's House. Amble around this vibrant area's lakeside or experience its fascinating museums.

Obama's House

What to do in South Side

Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

CA $145
per adult
86% of travellers recommend
Chicago C3® by CityPASS®
Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

CA $56
per adult
Field Museum of Natural History All-Access Pass
Chicago Fire FC Football Game at Soldier Field

Chicago Fire FC Football Game at Soldier Field

CA $19
per adult
Chicago Fire FC Football Game at Soldier Field
See all activities in South Side

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 CA $950. 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.