South Side Holidays from £675

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The Latest South Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Welcome Inn & Suites - Lyons

Welcome Inn & Suites - Lyons

2 out of 5
per person
24 Jun - 30 Jun
Return flight included
London (LON) to Chicago (MDW)
5.2/10 (43 reviews)
Staff was nice and helpful they allowed me an early check-in after my issues with the prior hotel they also offered us an upgrade and an extra day at the regular price

Reviewed on 8 May 2024

Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
O'Hare
per person
24 Jun - 30 Jun
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,321 reviews)
The hotel great problem with Expedia not resolved yet after 21 hours. Hopefully it happens.

Reviewed on 16 May 2024

The Brewery Lodge Hotel

The Brewery Lodge Hotel

3.5 out of 5
per person
25 Jun - 2 Jul
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (532 reviews)
Set in the woods with lots of trails to walk. Everyone worki g there (receptionist, bartender, cleaning people were very friendly and helpful.

Reviewed on 15 May 2024

Carlton Inn Midway

Carlton Inn Midway

2 out of 5
Archer Heights
per person
24 Jun - 30 Jun
Return flight included
London (LON) to Chicago (ORD)
7.2/10 Good! (1,002 reviews)
Nice that they had 24 hour airport pickup but the van was older and harder to get into than the one shown on website. If you have issues with getting into higher vehicle, take an uber. We got in late and they upgraded us, but no towels in room, it took a bit to get some, had to raid another room and the light bulbs in bathroom were burnt out. Staff is friendly and hard working, breakfast was standard and very welcome to have in an expensive city, short walk to the orange line that gets you everywhere and safe area right across from a high school, nothing fancy but clean and about right for price.

Reviewed on 14 May 2024

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
per person
25 Jun - 2 Jul
Return direct flight included
Manchester (MAN) to Chicago (ORD)
7.8/10 Good! (1,004 reviews)
People staying at the casino hotel can check in via a kiosk near the front desk or check in with someone at the desk. The woman who checked me in was very friendly and efficient. No issues and a quick process.

Reviewed on 14 May 2024

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
Highland Hills
per person
24 Jun - 30 Jun
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,517 reviews)
Comfortable beds. Clean room.

Reviewed on 16 May 2024

South Side Essential Information

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

Our guide on where to stay in South Side

Check out a few of the areas and neighbourhoods we love in South Side Learn more about South Side
South Loop which includes a city and a high-rise building

South Loop

3/5(3 area reviews)

South of downtown Chicago, this neighborhood features cultural activities, sports and convention centers and a great dining and nightlife scene.

Find hotels in South Loop

Our pick of the best South Side Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this family-friendly hotel in Chicago. Enjoy a 24-hour fitness centre, valet parking (surcharge) and in-room massages. Our guests praise the helpful ...
7.6/10 Good! (2,580 reviews)
"Very clean"

Reviewed on 14 May 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (6,723 reviews)
"Great location for walking to both museums and Magnificent Mile. Restaurants on site if you don't get out to eat. Late check out (noon)."

Reviewed on 14 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free Wi-Fi, room service and a fitness centre. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,867 reviews)
"I enjoyed staying in this hotel. Very convenient and nearby to tourist attractions. The staff are very accommodating. I will definitely book this hotel if I’m in Chicago."

Reviewed on 15 May 2024

River Hotel
See all 4,832 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

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 £675. 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.

Discover the most popular places to visit in South Side

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Unmissable things to do in South Side

Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

£81
Per adult
78% of travellers recommend
Chicago C3® by CityPASS®
Image for Chicago Shoreline Adventure Boat Tour

Chicago Shoreline Adventure Boat Tour

£71
Per adult
Chicago Shoreline Adventure Boat Tour
Image for Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

£32
Per adult
Field Museum of Natural History All-Access Pass
See all activities in South Side

* 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.