South Side Vacation Packages 2026 from $182

South Side flight + hotel vacation packages

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

Hilton Orrington / Evanston

Downtown Evanston

$182

per person

Feb 21 - Feb 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

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

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$787

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$588

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$594

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Pendry Chicago

Downtown Chicago

$548

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) 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.

Top South Side hotels deals

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

6500 S Cicero Ave Chicago IL

Free Cancellation

$112 nightly

$132 total

Dec 23 - Dec 24

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

SpringHill Suites by Marriott Chicago Chinatown

2357 S WENTWORTH AVE Chicago IL

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$119 total

Jan 1 - Jan 2, 2026

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

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$94 total

Dec 21 - Dec 22

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

Jaslin Hotel

261 West Cermak Rd Chicago IL

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$145 total

Jan 1 - Jan 2, 2026

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

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

Dec 29 - Dec 30

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

Sophy Hyde Park

1411 East 53rd Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$216 nightly

$253 total

Dec 28 - Dec 29

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. A terrace, a lobby fireplace, and a computer station are also on offer.

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

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

Griffin Museum of Science and Industry

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

Illinois Institute of Technology

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

Frequently asked questions

How much are vacation packages to South Side?

$182 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.