South Side Vacation Packages 2025/2026 from $286

South Side flight + hotel vacation packages

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

Hampton Inn Crown Point

per person

Sep 25 - Sep 28

found 12 hours ago

Roundtrip flight included

Minneapolis (MSP) to Chicago (ORD)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Self parking, a 24-hour business center, and luggage storage are also offered.

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 2 - Oct 5

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 luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

Save 100% on your flight

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Sep 5 - Sep 7

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.

The Chicago Hotel Collection River North

Downtown Chicago

Save 100% on your flight

per person

Oct 12 - Oct 19

found 13 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A lobby fireplace, express check-out, and luggage storage are also on offer.

Top South Side hotels deals

Jaslin Hotel

261 West Cermak Rd, Chicago, IL

Free Cancellation

$115 nightly

$136 total

Aug 18 - Aug 19

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

SpringHill Suites by Marriott Chicago Chinatown

2357 S WENTWORTH AVE, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Aug 24 - Aug 25

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

Motel 6 - Chicago, IL

10022 South Halsted Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$88 total

Aug 31 - Sep 1

Total includes 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

$149 nightly

$175 total

Aug 5 - Aug 6

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

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

Aug 25 - Aug 26

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

Carlton Inn Midway

4944 S Archer Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$140 total

Aug 5 - Aug 6

Total includes taxes and fees

This motel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free airport shuttle

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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

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.

Chicago 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?

$286 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.