South Chicago Vacation Packages 2025 from $294

The Latest South Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

per person

Aug 13 - Aug 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

8.4/10 Very Good! (4,263 reviews)

Good location, very nice breakfast. Attractive happy hour

Reviewed on Jul 9, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 13 - Aug 15

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (1,623 reviews)

Beautiful!! Location, room, security, everything was perfect! Very classy, elegant!

Reviewed on Jul 9, 2025

Pendry Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 13 - Aug 15

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (1,006 reviews)

It’s a great location for walk around the beautiful downtown of Chicago. People were so helpful and friendly. Definitely I’ll consider coming back.

Reviewed on Jul 7, 2025

The Emily Hotel

Downtown Chicago

Save 100% on your flight

per person

Aug 13 - Aug 15

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

9.2/10 Wonderful! (1,097 reviews)

Spacious room with a very comfortable bed, comfortable room temperature on a hot weekend, large bathroom and spacious work station. Close to trains that transport to the loop within minutes.

Reviewed on Jul 8, 2025

Hotel Riu Plaza Chicago

Downtown Chicago

per person

Aug 13 - Aug 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (2,065 reviews)

Everything was top notch from the Front Desk to the rooms and we truly enjoyed the breakfast buffet. Best breakfast I've experienced at any establishment that was included with your stay. When traveling, i'll make an effort to locate a Hotel Riu if there's one at my destination. Great experience.

Reviewed on Jul 9, 2025

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

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.

South Chicago Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

₩184,175

₩216,202 total

Aug 5 - Aug 6

includes taxes & fees

7.8/10 Good! (8,922 reviews)

"It’s a historical building so it does have its worn down look. Beautiful overall. I just wish it wasn’t so expensive"

Reviewed on Jul 8, 2025

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

Fully refundable

₩284,254

₩377,585 total

Aug 7 - Aug 8

includes taxes & fees

9/10 Wonderful! (1,998 reviews)

"The property is next to most restaurants, shopping mall and walking distance to Navy Pier"

Reviewed on Jul 7, 2025

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Fully refundableReserve now, pay when you stay

₩245,567

₩288,271 total

Jul 10 - Jul 11

includes taxes & fees

8.8/10 Excellent! (2,406 reviews)

"Excellent location. Only one block away from the lake as well as from the Michigan avenue (shopping area). Our room was nice and clean. I should not say room, it was like an one bedroom apartment without a kitchen. The management was very nice."

Reviewed on Jul 8, 2025

See all 4,238 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 ₩491,260. 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.