South Side Vacation Packages 2026 from $660

South Side flight + hotel vacation packages

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

Dorothy's

Lakeview

Save 100% on your flight

$660

per person

Jul 1 - Jul 6

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

Free WiFi in public areas, a communal living room, and luggage storage are available at this bed & breakfast. Enjoy the free continental breakfast each morning. Laundry facilities and a virtual front desk are also provided.

The Chicago Hotel Collection - Wrigleyville

Lakeview

Save 100% on your flight

$1,213

per person

Jun 27 - Jul 4

found 1 day ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A terrace, express check-in, and express check-out are also on offer.

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

$796

per person

May 14 - May 17

found 1 day ago

Roundtrip flight included

Mesa (AZA) to Chicago (ORD)

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$961

per person

May 14 - May 17

found 1 day ago

Roundtrip flight included

Mesa (AZA) 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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,280

per person

May 29 - Jun 1

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace 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

Apr 9 - Apr 10

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

Jaslin Hotel

261 West Cermak Rd Chicago IL

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$120 total

Apr 27 - Apr 28

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

SpringHill Suites by Marriott Chicago Chinatown

2357 S WENTWORTH AVE Chicago IL

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$157 total

Apr 13 - Apr 14

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

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

6500 S Cicero Ave Chicago IL

Free Cancellation

$125 nightly

$147 total

Apr 12 - Apr 13

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

Hyatt Place Chicago-South/University Medical Center

5225 S Harper Ave Chicago IL

$169 nightly

$198 total

Apr 19 - Apr 20

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

Chicago Lake Shore Hotel

4900 S Lake Shore Dr Chicago IL

$123 nightly

$144 total

Apr 25 - Apr 26

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

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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(1,186 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.

Rate Field

4/5(199 reviews)

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

Griffin Museum of Science and Industry

4.5/5(1,396 reviews)

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

Frequently asked questions

How much are vacation packages to South Side?

$660 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.