South Side Vacation Packages 2026 from $580

South Side flight + hotel vacation packages

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

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$580

per person

Oct 24 - Oct 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$751

per person

Sep 30 - Oct 6

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$941

per person

Oct 24 - Oct 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

The Peninsula Chicago

Downtown Chicago

Save 100% on your flight

$1,165

per person

Oct 24 - Oct 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the gym and perks like free WiFi.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$581

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

Top South Side hotels deals

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Free Cancellation

$124 nightly

$144 total

Sep 8 - Sep 9

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

Chicago Lake Shore Hotel

4900 S Lake Shore Dr Chicago IL

$149 nightly

$175 total

Sep 10 - Sep 11

Total with taxes and fees

Free self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. Luggage storage is also provided.

Pet friendly

Parking included

Jaslin Hotel

261 West Cermak Rd Chicago IL

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$168 total

Sep 1 - Sep 2

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

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$100 total

Sep 1 - Sep 2

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

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

6500 S Cicero Ave Chicago IL

Free Cancellation

$175 nightly

$206 total

Aug 25 - Aug 26

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 free newspapers.

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

$161 nightly

$192 total

Aug 30 - Aug 31

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

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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.

Stay near popular South Side attractions

A cityscape with historic buildings, a prominent church, and a view of the ocean.

University of Chicago

8.6/10 (3,689 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.

See properties

Frequently asked questions

How much are vacation packages to South Side?

$580 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.