South Side Holidays from £936

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    Save up to £750 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top South Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was £1,097, price is now £936 per person
£936
per person
4 Dec - 7 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £1,719, price is now £1,392 per person
£1,392
per person
1 Jan - 7 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was £1,662, price is now £1,393 per person
£1,393
per person
1 Jan - 7 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (479 reviews)

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £1,679, price is now £1,421 per person
£1,421
per person
1 Jan - 7 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,326 reviews)

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was £1,816, price is now £1,554 per person
£1,554
per person
1 Jan - 7 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)

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

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 Griffin Museum of Science and Industry.

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

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is £126 per night from 1 Nov to 2 Nov
£126
1 Nov - 2 Nov
includes taxes & fees
7/10 Good! (1,006 reviews)
"The room was spacious and clean. The bathroom was somewhat dated. The staff was very responsive, and the hotel was within walking distance of the Obama Library and the Museum of Science and Industry. The Hyde Park area of Chicago is lovely. The hotel was reasonably priced."

Reviewed on 28 Oct 2026

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

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundable
The price is £112 per night from 22 Nov to 23 Nov
£112
22 Nov - 23 Nov
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"Just so disgusted I can't even leave a review"

Reviewed on 27 Oct 2026

Holiday Inn Chicago – Midway Airport S by IHG
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
Fully refundableReserve now, pay when you stay
The price is £125 per night from 10 Nov to 11 Nov
£125
10 Nov - 11 Nov
includes taxes & fees
Jaslin Hotel
See all 513 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
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Family Friendly Holidays

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.
See properties

What to do in South Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Architecture River Tour from Michigan Avenue

Architecture River Tour from Michigan Avenue

£31
per adult
Architecture River Tour from Michigan Avenue
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 £936. 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

* 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.