South Side Vacation Packages 2026 from $372

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The Latest South Side vacation packages

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

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Save 100% on your flight

$372

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (2,046 reviews)

When we first walked in we were greeted and check in was fast. The room was nice and clean . Breakfast was decent . Overall we enjoyed our stay

Reviewed on Oct 4, 2026

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

$704

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Room was dated and showed signs of hard wear; front desk staff unfriendly; door men never once open the door for us from the street; area around hotel dirty. Shay, the concierge was super nice though and the lobby was attractively decorated.

Reviewed on Oct 4, 2026

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

Save 100% on your flight

$565

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,003 reviews)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$515

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,518 reviews)

Very clean!

Reviewed on Oct 4, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$667

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Everything at my residence was phenomenal. The bed was very comfortable, the kitchen was fully stocked with proper utensils. Make sure you look under the sink for the paper towel. The only setback was there should have been a make up/vanity mirror for the guest. One more thing with the windows open, you hear traffic really loudly, but when closed you hear nothing it is a very good property!!! I propose on this trip!! thank you so much for the opportunity.

Reviewed on Oct 4, 2026

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Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side

A classical building with a dome and columns, featuring Charlie Brown exhibit banners.

Hyde Park

3 out of top 10 points of interest in this area

Art and history abound in this architecturally impressive and leafy neighborhood between Washington Park and the shores of Lake Michigan.

A traditional Chinese building with ornate dragon carvings and colorful roof tiles.

Chinatown

If you're spending time in Chinatown, you might enjoy attractions like Chinese American Museum of Chicago and On Leong Building. You might also enjoy the neighborhood's ample dining options before hopping on the metro at Cermak-Chinatown Station to see more of the city.

A city skyline with illuminated buildings, a river, and a bridge.

Bridgeport

Well-liked for its restaurants and churches, Bridgeport is worth a visit. Check out the variety of things to see and do like Zhou B Art Center and Bridgeport Art Center, and jump on the metro at Halsted Station (Orange Line) to get around the city.

A modern bridge with a white arch spanning a highway, surrounded by greenery and urban buildings in the background.

Bronzeville

Travelers choose Bronzeville for its abundant dining options. Hop aboard the metro at 35th-Bronzeville-IIT Station or Indiana Station and check out top sights like Lake Michigan.

A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

Woodlawn

1 out of top 10 points of interest in this area

Woodlawn is well-liked for its beaches and restaurants. If you're hoping to get in some sightseeing, Lake Michigan and Obama Presidential Center are top spots, and you can jump on the metro at Cottage Grove Station or King Drive Station to get around.

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 fascinating museums in this vibrant area.

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A baseball stadium with advertisements, including 'xfinity' and 'proven IT'.

Rate Field

8.6/10 (235 reviews)

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

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Griffin Museum of Science and Industry

9.2/10 (1,796 reviews)

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

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A train passing through a tunnel with a curved roof and string lights.

Illinois Institute of Technology

7.0/10 (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.

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Barack Obama Residence

You can find out about the history of Chicago when you stop by Barack Obama Residence. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

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Rainbow Beach

Why not spend a lazy afternoon at Rainbow Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.

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Obama Presidential Center

You can spend an afternoon exploring the galleries in Obama Presidential Center during your trip to Chicago. Wander the beaches and gardens while you're in the area.

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Wabash Ave YMCA

You can find out about the history of Chicago when you stop by Wabash Ave YMCA. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

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What to do in South Side

360 CHICAGO Observation Deck

$24

per adult

86% of travellers recommend

Flyover in Chicago

$38

per adult

98% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour

$41

per adult

94% of travellers recommend

See all activities in South Side

South Side Hotel Deals

Jaslin Hotel

261 West Cermak Rd Chicago IL

Fully refundableReserve now, pay when you stay

$159 nightly

$189 total

Oct 15 - Oct 16

Total with taxes and fees

9/10 Wonderful! (1,391 reviews)

"Great Hotel, location is perfect in Chinatown a 2 minutes walk to the train."

Reviewed on Oct 4, 2026

Chicago Lake Shore Hotel

4900 S Lake Shore Dr Chicago IL

$135 nightly

$159 total

Nov 1 - Nov 2

Total with taxes and fees

7/10 Good! (1,002 reviews)

"Outside looks horrible. Inside looks fine."

Reviewed on Oct 4, 2026

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL

Fully refundable

$141 nightly

$164 total

Nov 2 - Nov 3

Total with taxes and fees

See all 497 properties in South Side

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.