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.
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 4
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
7.8/10 Good! (1,745 reviews)
A little dated but overall nice

Reviewed on May 13, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 1 - Jul. 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
I was pleasantly surprised to find artwork displayed throughout the property, including my favorite Kehinde Wiley.

Reviewed on May 12, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jun. 30 - Jul. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The best hotel hands down!

Reviewed on May 13, 2024

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 21 - Jul. 27
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very Good! (1,512 reviews)
room was spotless went throughout room w clorox wipe not a single spec of dirt !

Reviewed on May 13, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 24 - Jul. 1
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

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

4 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 Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips 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 $213 per night from May 15 to May 16
CA $213
CA $250 total
includes taxes & fees
May 15 - May 16
7.6/10 Good! (6,720 reviews)
Nice hotel, but dated.
"Hotel was in excellent location for my needs. The lobby and restaurant are in good shape. However, the rooms are needing an update. They were in very poor shape."

Reviewed on May 13, 2024

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
The price is CA $127 per night from May 27 to May 28
CA $127
CA $149 total
includes taxes & fees
May 27 - May 28
6.4/10 (1,640 reviews)
"I loved the location close to other attractions."

Reviewed on May 10, 2024

Travelodge by Wyndham Downtown Chicago
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 $150 per night from May 27 to May 28
CA $150
CA $176 total
includes taxes & fees
May 27 - May 28
7.8/10 Good! (2,544 reviews)
"Best Western-Grant Park and the most friendly staff on call most of the times. I did interact with one or two not so friendly members. But everyone else helpful and sweet which out weighed the others"

Reviewed on May 8, 2024

Best Western Grant Park Hotel
See all 4,150 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.

Explore other types of vacation packages

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 $1,380, 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.

Discover the most popular places to visit in South Loop

Image for McCormick Place

McCormick Place

4.5/5(141 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
Image for Soldier Field

Soldier Field

4.5/5(114 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Image for Shedd Aquarium

Shedd Aquarium

4.5/5(109 reviews)

Make time in your itinerary to visit the sea life you'll find at Shedd Aquarium during your visit to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Shedd Aquarium

Things to do

Image for Chicago C3® by CityPASS®

Chicago C3® by CityPASS®

CA $138
Per adult
78% of travellers recommend
Chicago C3® by CityPASS®
Image for Chicago Shoreline Adventure Boat Tour

Chicago Shoreline Adventure Boat Tour

CA $122
Per adult
Chicago Shoreline Adventure Boat Tour
Image for Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

CA $56
Per adult
Field Museum of Natural History All-Access Pass
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.