South Chicago Holidays

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Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
8/10 Very Good! (1,023 reviews)
Just too average for the price. If it was less money and same details, I’d have a little more appreciation for it.

Reviewed on 20 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Excellent service!!! Would highly recommend !! I have enjoyed this property many times and will return

Reviewed on 21 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (977 reviews)
The hotel was absolutely perfect for our quick weekend getaway. It was super comfortable, clean and safe. The staff was wonderful!

Reviewed on 19 May 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
29 Jun - 1 Jul
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
EXCEPTIONAL SERVICE!!

Reviewed on 21 May 2024

Where to stay in South Chicago

Find the best South Chicago areas and neighborhoods for the activities you enjoy most. Learn more about South Chicago
Downtown Chicago featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Top hotels in South Chicago

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is HK$976 per night from 27 May to 28 May
HK$976
per night
27 May - 28 May
7.6/10 Good! (2,594 reviews)
"Very cozy"

Reviewed on 20 May 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is HK$1,160 per night from 28 May to 29 May
HK$1,160
per night
28 May - 29 May
7.6/10 Good! (6,775 reviews)
Live History!
"Incredible building with such nostalgia and grace (definitely ask to check out the Gold Room on the second floor). Huge lofted rooms, with GREAT A/C and comfy beds! Wonderful location next to gorgeous parks, beautiful fountains, and a short walk to the lake. Close to the CSO, Art Institute, and sooooo ..."

Reviewed on 20 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is HK$1,253 per night from 27 May to 28 May
HK$1,253
per night
27 May - 28 May
8.6/10 Excellent! (2,888 reviews)
"Staff at the front desk are really helpful and friendly"

Reviewed on 19 May 2024

River Hotel
See all 3,951 properties in South Chicago
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.

Frequently asked questions

How much does a South Chicago vacation package cost?
Live it up in South Chicago from just HK$3,711. Choose from a wonderful selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add a few sightseeing activities to your vacation package.
How do I get a cheap travel package to South Chicago?
Combine your flights and hotels, toss in extras such as activities or a rental car, and save with a South Chicago holiday package. You won’t just pick up impressive discounts on your escape — you’ll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 partner airlines and 1,000,000 hotels around the globe. Your dream holiday starts right here, right now!
Where should I stay in South Chicago?
With so much to do in South Chicago, it’s a good idea to secure a room in a hotel close to its attractions. Calumet Beach, Calumet Park and Bronzeville Childrens Museum are some interesting ones to put on your must-see list.
How far in advance should I book my South Chicago holiday?
While not all airlines release ticket prices early, it’s usually possible to compare international fares on Expedia up to 12 months in advance. This is the time you can bag some fantastic bargains. If you’re purchasing tickets last minute, you might get lucky. Sometimes the cheapest prices emerge just weeks before departure.
What does an Expedia South Chicago travel package include?
From hotels and flights to car rentals, Expedia can help you craft a South Chicago package that fits you. Heading away for a week or longer? Consider a flight, rental car and hotel bundle. If you’re taking a quick break, a hotel and flight deal could suit you better. Tours and activities can be added after you’ve booked. Our packages make it a cinch to plan and save.
What should I know before booking a South Chicago travel package?
You’ll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up fantastic discounts. You’re not restricted to hotels, though. We’ve got island resorts, cosy city apartments and everything in between!
Can I choose my airline with a South Chicago Expedia holiday package?
Yes, of course. Expedia has access to more than 550 airline partners around the world, so fly with the carrier that best fits your budget and travelling style.
If I'm not able to travel, can I cancel my South Chicago holiday package?
If your holiday plans in South Chicago have changed, it’s good to know that it’s possible to cancel your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.

Popular places to visit

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 Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
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

Things to do

Image for Skyline Lake Tour

Skyline Lake Tour

HK$294
Per adult
92% of travellers recommend
Skyline Lake Tour
Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

HK$1,473
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
See all activities in Chicago

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.