West Loop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in West Loop

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was CA $878, price is now CA $589 per person
CA $589
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
7.4/10 Good! (1,004 reviews)
Quick stay in between traveling. The bed and bedding comfortable. Room is spacious. Staff friendly.

Reviewed on Aug. 30, 2025

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,831, price is now CA $1,198 per person
CA $1,198
per person
Oct 25 - Oct 29
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.

Reviewed on Aug. 24, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $1,922, price is now CA $1,279 per person
CA $1,279
per person
Oct 22 - Oct 25
found 16 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Half Day
Price was CA $882, price is now CA $594 per person
CA $594
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Very close to grocery stores, restaurants drugstores everything was nearby

Reviewed on Aug. 31, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,038, price is now CA $699 per person
CA $699
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 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 $246 per night from Sep 2 to Sep 3
CA $246
CA $289 total
Sep 2 - Sep 3
includes taxes & fees
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 $209 per night from Sep 4 to Sep 5
CA $209
CA $262 total
Sep 4 - Sep 5
includes taxes & fees
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 $310 per night from Sep 2 to Sep 3
CA $310
CA $395 total
Sep 2 - Sep 3
includes taxes & fees
Level Chicago Fulton Market
See all 4,802 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 $589, 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

Chicago: Fulton Market Donut Adventure with Tastings

Chicago: Fulton Market Donut Adventure with Tastings

CA $94
per adult
Chicago: Fulton Market Donut Adventure with Tastings
Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour

Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour

CA $10
per traveller
Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour
Marvels & Feats: An Engineer's Tour of Chicago Architecture

Marvels & Feats: An Engineer's Tour of Chicago Architecture

CA $48
per adult
Marvels & Feats: An Engineer's Tour of Chicago Architecture
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.