South Side Holidays from £892

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    Packages with flights are ATOL protected

Top South Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
Downtown Chicago
per person
9 Oct - 15 Oct
found 22 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
7.2/10 Good! (509 reviews)
There with a friend for a concert - we wanted someplace with easy access to the L Train. This was definitely it! We were on the 2nd floor with a window right next to the tracks and could barely hear the train go by. Didn't hear any of our neighbors, and the staff was always helpful and friendly!

Reviewed on 28 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Sept - 27 Sept
found 6 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Самый лучший отель в чикаго

Reviewed on 28 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Sept - 27 Sept
found 6 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
23 Sept - 27 Sept
found 6 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The hotel was nice, staff were friendly and the overall stay was excellent and convenient to walk.

Reviewed on 28 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
23 Sept - 27 Sept
found 6 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The hotel is beautiful inside and out and the staff are super nice and helpful. Hotel is in a very crowded area. It can take time to get in and out with your car. A lot of noise from the outside even when staying on top floors. Hotel could be managed better. Elevator was broken for a whole day. Room had some minor repairs that were not done when we checked in.

Reviewed on 28 Jul 2025

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
Chicago Museum of Science and Industry

Hyde Park

4 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.

Find hotels in Hyde Park

South Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Top hotels in South Side

Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
Fully refundable
The price is £104 per night from 13 Aug to 14 Aug
£104
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (1,098 reviews)
"I enjoyed my stay at this affordable hotel in Chinatown. The staff were great, my room was clean, and good food, public transit, and parking were all in easy walking distance."

Reviewed on 24 Jul 2025

Jaslin Hotel
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 out of 5
2357 S WENTWORTH AVE, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £149 per night from 24 Aug to 25 Aug
£149
24 Aug - 25 Aug
includes taxes & fees
9.4/10 Exceptional! (954 reviews)
"Hotel was in convenient location. Everything was walking distance."

Reviewed on 25 Jul 2025

SpringHill Suites by Marriott Chicago Chinatown
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £63 per night from 13 Aug to 14 Aug
£63
13 Aug - 14 Aug
includes taxes & fees
6/10 (48 reviews)
"I appreciate all the people that work at this motel 6! They are polite and always willing to help with reservations. I also have a service animal and it's been so peaceful to stay there."

Reviewed on 17 Jul 2025

Motel 6 - Chicago, IL
See all 457 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Robie House

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 galleries in this vibrant area.

University of Chicago
Robie House

Robie House

Witness the simple beauty of Frank Lloyd Wright’s designs in a Chicago house that epitomizes a popular American style of architecture.

Robie House

What to do in South Side

Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£78
per adult
86% of travellers recommend
Chicago C3® by CityPASS®
Field Museum of Natural History Ticket with Self-Guided Audio Tour

Field Museum of Natural History Ticket with Self-Guided Audio Tour

£47
per adult
100% of travellers recommend
Field Museum of Natural History Ticket with Self-Guided Audio Tour
Bike Tour

Chicago's Ultimate City Bike Tour

£45
per adult
100% of travellers recommend
Chicago's Ultimate City Bike Tour
See all activities in South Side

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 £892. 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.

* 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.