West Loop Vacation Packages

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Top Holiday Package Deals in West Loop

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,374 reviews)
The property was nice just wish they had a pool.

Reviewed on Jul. 30, 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
Convenient location for our stay in Chicago. Room could use updating, carpet could use deep cleaning.

Reviewed on Jul. 31, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The room is clean and spacious. The river view is also beautiful especially night time. And facilities are all clean and well maintained. Good place to enjoy

Reviewed on Jul. 31, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Great helpful staff! Very clean! Wonderful experience! Breakfast buffet is a must! So delicious

Reviewed on Jul. 31, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on Jul. 30, 2025

Where to stay in West Loop

Find the best West Loop areas and neighborhoods for the activities you enjoy most. Learn more about West Loop
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

West Loop Hotel Deals

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 $202 per night from Aug 24 to Aug 25
CA $202
CA $237 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,324 reviews)
"It is renovated, it is very clean, the breakfast was delicious"

Reviewed on Jul. 30, 2025

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street, Chicago, IL
Fully refundable
The price is CA $223 per night from Aug 24 to Aug 25
CA $223
CA $278 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
"Excellent location!"

Reviewed on Jul. 31, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
354 North Union Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $278 per night from Aug 10 to Aug 11
CA $278
CA $353 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (253 reviews)
"We were pleasantly surprised and now already planned our next trip in a couple weeks to stay at the same hotel. Only concern is we were told pool area was open and hour after rooftop. That is mot correct and bed in single studio is too close to the wall. Had to crawl out as my wife sleep on the otherside. ..."

Reviewed on Jul. 28, 2025

Level Chicago Fulton Market
See all 4,694 properties in West 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 West Loop vacation package cost?
Our West Loop packages, which start from just CA $747, are the best way to save money. Handpick your favorite flights, hotels and rental cars to create a personalized getaway.
How do I get a cheap travel package to West Loop?
If you love bargains, bundle your bookings into a West Loop vacation package. Whether you need flights, hotels, tours or rental cars, you can browse and book them all in one place. You'll have lots of choice at your fingertips as well. Expedia has more than 550 air carriers and 1,000,000 hotels worldwide to select from. Fly with who you want, book a room where you like and save some cash — now that's the ideal getaway!
Where should I stay in West Loop?
Make sightseeing easier by staying someplace just around the corner from West Loop's biggest attractions. University of Illinois Chicago and United Center are two which top many visitors' bucket lists.
What are the top hotels in West Loop?
Book a room at The Hoxton Chicago. It's one of this area's most sought-after hotels. Another great option in West Loop is Hyatt House Chicago West Loop.
How far in advance should I book my West Loop vacation?
It can be hard to know when the best time is to book your vacation to West Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can lock in your flights and hotels up to a year prior to your departure date. If you're considering a last-minute getaway, no need to stress! There are fantastic deals advertised on Expedia every single day.
What does an Expedia West Loop travel package include?
Hotels, flights and a reliable car for your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a few sightseeing tours and watch your savings pile up. When it comes to planning your West Loop getaway, you're in charge!
What should I know before booking a West Loop travel package?
Whether it's relaxation or adventure you're chasing, a West Loop vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a West Loop Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my West Loop vacation package?
Don't stress if you're rethinking your West Loop vacation package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We know life can occasionally throw a spanner in the travel works, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

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.