South Side Vacation Packages 2026 from $145

South Side flight + hotel vacation packages

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

Red Roof Inn PLUS+ Chicago - Willowbrook

$145

per person

Apr 24 - Apr 27

found 16 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A safe deposit box is also provided.

La Banque Hotel

$395

per person

Apr 23 - Apr 27

found 23 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. 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 concierge services.

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

$409

per person

May 1 - May 3

found 14 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$580

per person

May 11 - May 14

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Viceroy Chicago

Downtown Chicago

Save 100% on your flight

$612

per person

May 11 - May 14

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Top South Side hotels deals

SpringHill Suites by Marriott Chicago Chinatown

2357 S WENTWORTH AVE Chicago IL

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$129 total

Feb 22 - Feb 23

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

$100 nightly

$118 total

Feb 22 - Feb 23

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

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

6500 S Cicero Ave Chicago IL

Free Cancellation

$105 nightly

$123 total

Feb 18 - Feb 19

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

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Free Cancellation

$96 nightly

$111 total

Feb 17 - Feb 18

Total with taxes and fees

This hotel features a restaurant, a 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 coffee shop, and a snack bar/deli are also offered.

Free WiFi

Restaurant

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$94 total

Feb 16 - Feb 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

Hyatt Place Chicago-South/University Medical Center

5225 S Harper Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$158 total

Feb 22 - Feb 23

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

Aerial View of a large University in the Chicago Neighborhood of Hyde Park

University of Chicago

4.5/5(1,167 reviews)

Enjoy the collegiate vibe when you visit University of Chicago, during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Chicago Museum of Science and Industry which includes shopping and interior views as well as a large group of people

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.

U.S. Cellular Field is the 4th MLB stadium that I have visited. The main thing that stands out about my visit is that it was really warm out in the sun, but it felt like the temperature dropped 20-30 degrees in the shade. Awesome stop in Chicago.

Rate Field

4/5(199 reviews)

Catch an event at Rate Field during your trip to Chicago. Experience the entertainment choices and acclaimed art scene in this vibrant area.

Frequently asked questions

How much are vacation packages to South Side?

$145 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.