South Side Vacations from $415

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The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
Well kept, great location and friendly staff!

Reviewed on May 31, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 7 - Aug 12
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 25
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Property is 5 star all the way. Staff is excellent. Restaurant is 5 star as well.

Reviewed on Jun 6, 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (664 reviews)
Nice property, excellent service. Hallways are showing a little wear. We have visited the Emily since its opening. Great neighborhood and nice hotel. Just a bit worn in the 3rd floor hallway.

Reviewed on Jun 2, 2024

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 25
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Great property. I’ve stayed here numerous of times. Love the area too. Lots of great places to eat.

Reviewed on Jun 4, 2024

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
South Loop featuring a skyscraper and a city

South Loop

4.5/5(607 area reviews)

South of downtown Chicago, this neighborhood features cultural activities, sports and convention centers and a great dining and nightlife scene.

Find hotel + flight trips in South Loop

South Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

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 $167 per night from Jun 16 to Jun 17
$167
$196 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,859 reviews)
"Friendly check in, gorgeous historic building. Room was great, bed and pillows comfortable, fresh. Charger ports on night stands. The water - lake view was absolutely worth the sunrise over Lake Michigan! Parked in. GRANT Parking South underground lot for about half the $62 parking next to the hotel, ..."

Reviewed on Jun 7, 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 $153 per night from Jul 8 to Jul 9
$153
$180 total
includes taxes & fees
Jul 8 - Jul 9
8.6/10 Excellent! (2,950 reviews)
"Excellent stay for us. The room was clean and comfortable. The staff was exceptional. Very professional and friendly. Couldn't ask for a better experience. Thanks."

Reviewed on Jun 5, 2024

River Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $211 per night from Jun 17 to Jun 18
$211
$247 total
includes taxes & fees
Jun 17 - Jun 18
8/10 Very Good! (2,368 reviews)
"Had a great stay. Would definitely come back"

Reviewed on Jun 6, 2024

Embassy Suites by Hilton Chicago Downtown River North
See all 4,809 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

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 $415. 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.

Discover the most popular places to visit in South Side

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

What to do in South Side

Image for Prairie Avenue Haunted History Tour and Ghost Hunt

Prairie Avenue Haunted History Tour and Ghost Hunt

$40
Per adult
Prairie Avenue Haunted History Tour and Ghost Hunt
Image for Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

$55
Per adult
Chicago's Ultimate City Bike Tour
Image for Small Group Lake Michigan Tour

Small Group Lake Michigan Tour

$60
Per adult
Small Group Lake Michigan Tour
See all activities in South Side

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.