South Side Holidays

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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

Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.

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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 neighbourhood's ample dining options before hopping on the metro at Cermak-Chinatown Station to see more of the city.

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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 Bridgeport Art Center and Ramova Theatre, and jump on the metro at Halsted Station (Orange Line) to get around the city.

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

Bronzeville

1 out of top 10 points of interest in this area

Consider exploring the abundant dining options in Bronzeville. If sightseeing is on the list, Lake Michigan is a top attraction. Hop on the metro at 35th-Bronzeville-IIT Station or Indiana Station to see more of the area.

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A cityscape with a prominent skyscraper, a large bridge, and a distant body of water.

Douglas

1 out of top 10 points of interest in this area

If you're spending time in Douglas, you might enjoy attractions like Lake Michigan and Ida B Wells House. You might also enjoy the neighbourhood's ample dining options before hopping on the metro at 35th-Bronzeville-IIT Station to see more of the city.

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Top hotels in South Side

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

4900 S Lake Shore Dr Chicago IL
S$251
20 Sept - 21 Sept
includes taxes & fees
7/10 Good! (1,017 reviews)
"Internet connection sucked and was not informed of security deposit until we got there"

Reviewed on 8 Sept, 2026

Chicago Lake Shore Hotel
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

7353 S Cicero Avenue Chicago IL
Fully refundable
S$238
27 Sept - 28 Sept
includes taxes & fees
Holiday Inn Chicago – Midway Airport S by IHG
Jaslin Hotel

Jaslin Hotel

261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
S$242
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (1,352 reviews)
"I honestly loved staying here, if you are trying to stay in chicago on a budget, here is your place. Best place you are going to stay for the price. It is close to the city and lot of options to choose to eat. It has everything you need. Id recommend this place to anyone visiting chicago."

Reviewed on 9 Sept, 2026

Jaslin Hotel
See all 473 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.

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 theatre scene in this vibrant area.
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A classical building with a dome and columns, featuring Charlie Brown exhibit banners.

Griffin Museum of Science and Industry

9.2/10 (1,796 reviews)
A large museum close to downtown Chicago with plenty for all ages to see and do, with exhibits including a coal mine and World War II submarine.
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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)
Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.
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A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

Jackson Park

7.4/10 (9 reviews)
Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.
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Barack Obama Residence

You can find out about the history of Chicago with a stop at Barack Obama Residence. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.
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Obama Presidential Center

You can spend an afternoon browsing the exhibits at Obama Presidential Center in Chicago. Wander the beaches and gardens while you're in the area.
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Ida B Wells House

You can find out about the history of Chicago with a visit to Ida B Wells House. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
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What to do in South Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in South Side

Frequently asked questions

How much does a South Side holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in South Side from just . And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to South Side?
Book everything in the one place with our South Side holiday packages. You'll find deals on flights, hotels and more that'll keep your pocket happy and your adventurous side busy. And, with more than 550 air carriers and 1,000,000 hotels throughout the world to pick from, you'll have the flexibility to mix and match all you want.
What are the top hotels in South Side?
When it comes to properties in Carville, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are a couple of favourites. If you're considering heading to Chatham Fields, The Whitehall Hotel and Hyatt Regency Chicago are waiting to welcome you.
How far in advance should I book my South Side holiday?
While not all airlines advertise ticket prices early, it's usually possible to look up international flights on Expedia up to a year in advance. This is the time you can bag some incredible deals. If you're purchasing tickets last minute, there's a chance you could get lucky. Sometimes the lowest prices become available a few weeks prior to departure.
What does an Expedia South Side travel package include?
Expedia has everything you need to book your South Side escape, but what your package looks like is up to you. Choose from a combination of rental cars, hotels and flights. Searching for some activities to keep you busy? Once you've made your booking, you can add them on too. Whatever your style or budget, there's a package deal to suit your needs.
What should I know before booking a South Side travel package?
Discover deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we're a one-stop shop for all of them. You'll save precious cash just for combining your bookings. Whether you're embarking on a ski trip or relaxing on a sunny beach, your perfect getaway is only clicks away.
Can I choose my airline with a South Side Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to choose from all over the world. With so many choices, finding the right carrier to bring you to South Side will be a snap.
If I'm not able to travel, can I cancel my South Side holiday package?
You can. We get that even the best-laid plans can go awry, so we're here to help if you have to make changes to your South Side holiday package. It may be possible to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.