South Chicago Packages (Flight + Hotel)

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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

Top hotels in South Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on 25 Sept 2025

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Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿3,192 per night from 27 Oct to 28 Oct
฿3,192
฿5,262 total
27 Oct - 28 Oct
includes taxes & fees
7.8/10 Good! (2,388 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on 24 Sept 2025

Freehand Chicago
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
The price is ฿6,490 per night from 29 Oct to 30 Oct
฿6,490
฿7,619 total
29 Oct - 30 Oct
includes taxes & fees
8.4/10 Very Good! (4,985 reviews)
"Clean room, staff was friendly & helpful. Location was perfect for us"

Reviewed on 25 Sept 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,308 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

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
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
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

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

Chicago C3® by CityPASS®

฿3,378
per adult
84% of travellers recommend
Chicago C3® by CityPASS®
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

฿1,434
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
River tour boat in Chicago

Architecture River Tour

฿1,554
per adult
96% of travellers recommend
Architecture River Tour
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.