South Side Vacation Packages 2025/2026 from $266

South Side flight + hotel vacation packages

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

theWit Chicago, a Hilton Hotel

Downtown Chicago

$266

per person

Jan 16 - Jan 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

$363

per person

Jan 16 - Jan 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

Pendry Chicago

Downtown Chicago

$379

per person

Jan 16 - Jan 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Level Chicago – Old Town

Downtown Chicago

$533

per person

Jan 16 - Jan 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

The Blackstone, Autograph Collection

Downtown Chicago

Save 100% on your flight

$334

per person

Jan 16 - Jan 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-in are also offered.

Top South Side hotels deals

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

6500 S Cicero Ave, Chicago, IL

Free Cancellation

$116 nightly

$136 total

Dec 14 - Dec 15

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free airport shuttle

Motel 6 - Chicago, IL

10022 South Halsted Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$88 total

Nov 16 - Nov 17

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. Laundry facilities are provided for your convenience.

Pet friendly

Parking included

SpringHill Suites by Marriott Chicago Chinatown

2357 S WENTWORTH AVE, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$136 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free WiFi

Jaslin Hotel

261 West Cermak Rd, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$137 total

Nov 27 - Nov 28

Total with taxes and fees

A 24-hour gym is featured at this hotel, along with free WiFi in public areas and luggage storage. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.

Free WiFi

Air conditioning

Saratoga Motel By Capital O Near Midway Airport Chicago IL

7701, S Cicero Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$95 total

Nov 17 - Nov 18

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Parking included

Free WiFi

Hyatt Place Chicago-South/University Medical Center

5225 S Harper Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$187 total

Dec 7 - Dec 8

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A free area shuttle is offered as well.

Pet friendly

Free WiFi

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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.

Popular places to visit

University of Chicago

4.5/5(1,167 reviews)

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.

Griffin Museum of Science and Industry

4.5/5(1,381 reviews)

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

Illinois Institute of Technology

3.5/5(4 reviews)

Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.

Frequently asked questions

How much are vacation packages to South Side?

$266 is all you'll need for a fantastic break in South Side. Bundle your hotel and flights into a Travelocity vacation package and see your savings add up. With such good prices, it's never been more tempting to travel.

Where can I get the best vacation package deals for South Side?

Travelocity is the place to go to score a terrific South Side package deal. Select from as many as 400 air carriers and 1,000,000 properties around the world and create a travel itinerary that suits your style. With this amount of choice, you'll have plenty of inspiration for your next big adventure.

Why should I book my South Side vacation bundle via Travelocity?

Whether you're on the hunt for the ultimate unplugged vacation or you crave the hustle and bustle that only a big city can provide, booking everything with Travelocity saves you time, hassle and money. No need to scour through countless websites for the best deal — our Price Match Guarantee ensures you'll always score the lowest possible price, and our team of customer service experts are available 24/7.

Will I save money on my South Side car rental if I combine it with a hotel or flight?

Combining your bookings into a South Side vacation package will certainly save you money. You can combine a car and flight; a flight, hotel and car; or a car and hotel. There's no better way to explore the greater South Side area than from the driver's seat of your own rental car. You can also add activities and experiences to your Travelocity package.

Which airport is best for South Side?

O'Hare Intl. Airport (ORD) is a great option for travelers flying to South Side. Midway Intl. Airport (MDW) and Lewis University Airport (LOT) also welcome many of the region's flights.

What is there to do in South Side?

A vibrant and impressive destination, South Side boasts some fantastic sights and attractions. University of Chicago and Chicago Museum of Science and Industry are just a couple of the local highlights.