South Chicago Holidays

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Our guide on 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

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Our pick of the best South Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$266 per night from 14 Feb to 15 Feb
NZ$266
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,821 reviews)
Yes perfectly clean

Reviewed on 24 Jan 2026

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$208 per night from 5 Feb to 6 Feb
NZ$208
5 Feb - 6 Feb
includes taxes & fees
8.4/10 Very Good! (5,583 reviews)
Always a great stay, clean, great breakfast, great pool.

Reviewed on 22 Jan 2026

Embassy Suites by Hilton Chicago Downtown River North
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$263 per night from 11 Feb to 12 Feb
NZ$263
11 Feb - 12 Feb
includes taxes & fees
9.2/10 Wonderful! (3,232 reviews)
Perfect

Reviewed on 24 Jan 2026

Hotel Riu Plaza Chicago
See all 4,525 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 holiday package cost?
Live it up in South Chicago from just . 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 holiday 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.

Discover the most popular places to visit in South Chicago

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

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
Navy Pier featuring a sunset and rides

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

NZ$85
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
Art Institute of Chicago

Art Institute of Chicago

NZ$70
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.