South Chicago Vacations

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Your South Chicago Vacation

Booking a South Chicago vacation package is a wonderful way to become acquainted with this unique neighborhood. From its must-visit places to its little-known delights, you won't be short of new adventures. Kick start your trip to South Chicago by visiting nearby attractions such as Jackson Park, Calumet Park and Calumet Beach. Stop daydreaming and start doing. When you're ready to book your dream vacation to South Chicago, Expedia will help get you there.

The Latest South Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,028 reviews)
Had everything I needed in walking distance, felt like the Hotel had everything I needed.

Reviewed on May 29, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 29
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,001 reviews)
They didn’t have free wifi

Reviewed on May 28, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 20
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (208 reviews)
Loved all the neighborhood dogs & farmers market

Reviewed on May 20, 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 29
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,136 reviews)
Close go downtown tourist sites.

Reviewed on May 27, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,200 reviews)
The spa was underwhelming. Everything else was great.

Reviewed on Jun 1, 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 showing a city

Downtown Chicago

4 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 hotel + flight trips in Downtown Chicago

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 $188 per night from Jun 17 to Jun 18
$188
$221 total
includes taxes & fees
Jun 17 - Jun 18
7.6/10 Good! (6,816 reviews)
"Be aware there is only Analog TV in the room"

Reviewed on May 29, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundable
The price is $166 per night from Jul 1 to Jul 2
$166
$195 total
includes taxes & fees
Jul 1 - Jul 2
8.6/10 Excellent! (2,912 reviews)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal."

Reviewed on May 28, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $170 per night from Jun 30 to Jul 1
$170
$200 total
includes taxes & fees
Jun 30 - Jul 1
8.4/10 Very Good! (2,000 reviews)
"Liked everything basically. Sink in bathroom didn't drain properly, it was taking care of promptly, front desk personnel was outstanding, specially Robert."

Reviewed on May 31, 2024

Eurostars Magnificent Mile
See all 3,949 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a South Chicago vacation package cost?
Live it up in South Chicago from just $247. 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 vacation 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 vacation 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 vacation?
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, cozy city apartments and everything in between!
Can I choose my airline with a South Chicago Expedia vacation 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 traveling style.
If I'm not able to travel, can I cancel my South Chicago vacation package?
If your vacation 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

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 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

4.5/5(347 reviews)

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(1,805 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 Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$188
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
94% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$89
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

Other vacations you might like

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