South Side Holidays from £855
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Top South Side Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
£866
per person
19 Nov - 25 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
1. The shower was a little tricky.
2. There were no bags in the room for dirty clothes that were going home.
Staff
1. All of the staff was excellent and helpful. Rebecca at the concierge desk was very very helpful, patient and kind with any question asked of her.
2. Breakfast was really good.
3. The rooftop is a great place to unwind and grab a bite after a long day.
Reviewed on 13 Sept 2026
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
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.
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.
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.
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.
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.
South Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Top hotels in South Side
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
£147
20 Sept - 21 Sept
includes taxes & fees
7/10 Good! (1,002 reviews)
"Good"
Reviewed on 12 Sept 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
£139
27 Sept - 28 Sept
includes taxes & fees
Jaslin Hotel
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
£145
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (1,363 reviews)
"The parking could be better"
Reviewed on 13 Sept 2026
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
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.
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.
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.
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.
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.
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.
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.
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.
What to do in South Side
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Frequently asked questions
How much does a South Side travel package cost?
We make it simple to explore the world, with South Side packages starting from as low as £855. You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate escape, why not add a couple of experiences and tours to your travel itinerary?
If I'm not able to travel, can I cancel my South Side travel package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or alter your South Side travel package for free within 24 hours of booking. For bookings older than that, you can still cancel or make changes, but your hotel, car rental company or airline may charge additional fees. Need more information? Have a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to South Side?
Think of all the awesome things you could do in South Side with extra cash in your wallet. Watch your savings stack up when you combine your airfare and hotel bookings into a South Side holiday package. You have plenty of choice when you book with Expedia too. In fact, you can select from more than 550 air carriers and 1,000,000 properties around the world. Whether you're heading away with the family or going it alone, planning a getaway to South Side is better with a package.
Does Expedia offer Book Now, Pay Later South Side holidays?
Expedia has partnered with online lender Klarna to make your next getaway a bit easier on the wallet. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more money to play with while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Consider these flexible payment options:
- Pay monthly holidays: Klarna offers manageable monthly payment plans that suit all budgets, so you can have that well-earned holiday now.
- Pay in instalments holidays: If you'd like to pay off your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you secure your getaway.
How far in advance should I book my South Side holiday?
Browse Expedia to compare international fares ASAP. You can generally purchase a ticket up to a year before departure. If you can't find your preferred air carrier, or you've left things to the last minute, don't worry. Cheap fares to South Side sometimes occur just weeks before departure.
What does an Expedia South Side travel package include?
Expedia has all you need to lock in South Side trip, but how your package is structured is up to you. Choose from a combination of flights, rental cars and hotels. Searching for some tours or experiences to keep you on the go? Once you've made your booking, you can add them too. No matter your budget, there's a package to suit your needs.
What should I know before booking a South Side travel package?
A package can be easier on the bank balance than separately booking everything you need for your escape. For example, combine your flights, hotels and rental cars and save a packet. No matter your holiday plans, there's bound to be a package that suits your budget.
Can I choose my airline with a South Side Expedia travel package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Just pick your preferred air carrier and craft the perfect South Side getaway.
Explore a world of travel with Expedia
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- Flights to Chicago
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- Art Institute of Chicago
- Blue Island Holidays
- Visit Downtown Chicago
- Visit Grand Boulevard
- Chicago Harbor Lighthouse
- Visit Magnificent Mile
- Visit Near South Side
- Visit Prairie District
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- Chicago Riverwalk
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- Visit The Loop
- Chicago Theatre
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- Lincoln Hall
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- Lincoln Park Holidays
- Michigan Avenue
- Millennium Park
- Montrose Beach
- Navy Pier
- Robie House
- Shops at North Bridge
- The Loop Holidays
- Unity Temple
- Willis Tower
- Wrigley Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
