South Loop Vacation Packages

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Top Holiday Package Deals in South Loop

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
Jun. 12 - Jun. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Great property in Chicago. Quiet rooms

Reviewed on Apr. 28, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 18 - Jun. 23
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
8.8/10 Excellent! (1,988 reviews)
Stayed at Swissotel but very close to Hyatt Regency Chicago (0.2 miles) where my meeting was held.

Reviewed on Apr. 30, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 12 - Jun. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Love the rooftop! You get a beautiful view of the city.

Reviewed on Apr. 30, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 18 - Jun. 23
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.4/10 Exceptional! (3,465 reviews)
Loved the location, the best roof top in Chicago!

Reviewed on Apr. 27, 2025

Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
Jun. 23 - Jun. 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.4/10 Very Good! (24 reviews)
Parking is difficult. Closest designated spot was 2 blocks away. Booking was easy enough but communication between site and accommodation was inefficient. Email was not passed on for final access instructions to unmanned accommodation site. The finalisation process did not allow for visitors with International phone numbers to be contacted directly either. Login does not accept driver's licence picture.

Reviewed on Apr. 28, 2025

Where to stay in South Loop

Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South Loop
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

South Loop 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 $165 per night from May 27 to May 28
CA $165
CA $193 total
includes taxes & fees
May 27 - May 28
7.8/10 Good! (8,715 reviews)
"Really nice hotel next to millennium park."

Reviewed on Apr. 28, 2025

Congress Plaza Hotel
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from May 26 to May 27
CA $123
CA $144 total
includes taxes & fees
May 26 - May 27
8/10 Very Good! (2,505 reviews)
"Very nice employees"

Reviewed on Apr. 28, 2025

Best Western Grant Park Hotel
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $241 per night from May 9 to May 10
CA $241
CA $324 total
includes taxes & fees
May 9 - May 10
8.2/10 Very Good! (1,808 reviews)
My min vacation
"My room was very nice the staff was very very nice and friendly. I will be back again. The breakfast nice as well. My grandson loves the pool that’s all he wanted to do"

Reviewed on Apr. 28, 2025

Hilton Chicago
See all 4,206 properties in South Loop
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a South Loop vacation package cost?
Starting from a low CA $851, a vacation package is your passport to low-cost travel. Custom make your South Loop escape by selecting from our extensive range of hotels, flights and rental cars.
How do I get a cheap travel package to South Loop?
Creating your own South Loop vacation package with Expedia is a simple way to save. We have more than 550 airlines and 1,000,000 properties spread across the globe. With such a wonderful range to pick from, you’ll have no trouble creating your next dream getaway.
Where should I stay in South Loop?
Make sightseeing a breeze by staying someplace close to South Loop’s iconic attractions. McCormick Place and Millennium Park are two of the best in the area.
What are the top hotels in South Loop?
Sonder South Wabash and Hotel BnB are a couple of the most sought-after properties in South Loop. Why not take a look at the rates and facilities at each and then decide?
How far in advance should I book my South Loop vacation?
It can be tricky to know when the best time is to book your trip to South Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to 12 months before departure. If you’re hoping for a last-minute getaway, no need to worry! There are fantastic deals posted on Expedia all the time.
What does an Expedia South Loop travel package include?
That depends on what type of getaway you’re thinking about. South Loop vacation deals can include hotels, car rentals and flights. You can mix and match to create the package that fits your needs. You can also add on experiences and activities after you’ve booked to score even bigger discounts.
What should I know before booking a South Loop travel package?
So many places to wander around, so many things to see and do. With a package, you can check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a South Loop Expedia vacation package?
You sure can. Expedia has access to more than 550 partner airlines worldwide, so choose the carrier that’s a good fit for your needs.
If I'm not able to travel, can I cancel my South Loop vacation package?
Yes, you can cancel your South Loop booking if your travel plans have been upended. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Things to do

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

Chicago C3® by CityPASS®

CA $147
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
Chicago's Dark Side Smartphone

Chicago's Dark Side Self-Guided Smartphone Walking Tour

CA $14
per adult
98% of travellers recommend
Chicago's Dark Side Self-Guided Smartphone Walking Tour
Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

CA $57
per adult
Field Museum of Natural History All-Access Pass
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.