South Side Vacation Packages 2025 from $348

South Side flight + hotel vacation packages

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

La Banque Hotel

Save 100% on your flight

per person

Jul 5 - Jul 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Palmer House a Hilton Hotel

Downtown Chicago

Save 100% on your flight

per person

Aug 7 - Aug 11

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 historic 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 limo/town car service.

Hilton Garden Inn Naperville/Warrenville

Save 100% on your flight

per person

Aug 6 - Aug 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and a grocery/convenience store are also offered.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 6 - Aug 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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

per person

Jul 20 - Jul 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

Top South Side hotels deals

Jaslin Hotel

261 West Cermak Rd, Chicago, IL

Free Cancellation

$143 nightly

$168 total

Jun 23 - Jun 24

Total includes taxes and fees

A 24-hour gym is featured at this hotel, along with luggage storage and a safe deposit box. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.

Air conditioning

Gym

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

6500 S Cicero Ave, Chicago, IL

Free Cancellation

$127 nightly

$149 total

Jun 15 - Jun 16

Total includes 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

$144 nightly

$169 total

Jun 29 - Jun 30

Total includes 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

Hyatt Place Chicago-South/University Medical Center

5225 S Harper Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$177 total

Jun 29 - Jun 30

Total includes 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

Chinatown Hotel Chicago

214 West 22nd Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$105 total

Jun 12 - Jun 13

Total includes taxes and fees

Free WiFi in public areas, a communal living room, and express check-out are available at this hotel. Luggage storage and a safe deposit box are also provided.

Free WiFi

Air conditioning

Admiral Motel By Oyo Chicago I-94

9118 S Cottage Grove Ave, Chicago, IL

Free Cancellation

$72 nightly

$84 total

Jun 8 - Jun 9

Total includes taxes and fees

Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free parking.

Pet friendly

Parking included

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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 theater scene in this vibrant area.

Chicago 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 art scene and fascinating museums in this vibrant area.

Frequently asked questions

How much are vacation packages to South Side?

$348 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.