South Chicago Vacation Packages

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Top Holiday Package Deals in South Chicago

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
The property was great. There was a doorman that was great. His name was Spiro and he gave great food recommendations. I highly recommend this place.

Reviewed on Aug. 5, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Bad room service, bad dinner/breakfast service at the restaurants and no house keeping - had to ask for it - and when they finally did they didn’t restock the bar or towels.

Reviewed on Aug. 4, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul. 27, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
Beautiful hotel close to all the best parts of Chicago. Wonderful stay. Cant wait to go back!

Reviewed on Aug. 5, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
Sep 10 - Sep 17
found 2 days ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on Aug. 3, 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 showing 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

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 CA $185 per night from Aug 6 to Aug 7
CA $185
CA $217 total
Aug 6 - Aug 7
includes taxes & fees
7.8/10 Good! (8,940 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug. 1, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 21 to Aug 22
CA $239
CA $315 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,825 reviews)
"The iconic and historic hotel are a magnificent landmark and there’s a thrill to entering the lobby every time!"

Reviewed on Aug. 4, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,335 reviews)
"Thanks beautiful place"

Reviewed on Aug. 3, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,466 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.
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Frequently asked questions

How much does a South Chicago vacation package cost?
Live it up in South Chicago from just CA $1,236. 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

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.