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
May 8 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,988 reviews)
Went here for NYE. Perfect location to see the Navy Pier fmand Chicago River fireworks! Easy parking and super walkable..literally near EVERYTHING!

Reviewed on Mar. 25, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 30 - Jun. 2
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,310 reviews)
Great stay on St. Patrick's Day weekend.

Reviewed on Mar. 24, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 30 - Jun. 2
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Everything else is perfect, but the small room has a few issues. It smells like urine and lacks ventilation, making it very hot inside.

Reviewed on Mar. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Excellent, just what anyone would expect from this brand.

Reviewed on Mar. 25, 2025

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 27 - May 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,644 reviews)
Not enough towels and bathroom was not clean very well toilet seat still have pee I luckily brought cleaning stuff

Reviewed on Mar. 26, 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

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

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 $156 per night from Apr. 3 to Apr. 4
CA $156
CA $183 total
includes taxes & fees
Apr 3 - Apr 4
8.6/10 Excellent! (1,021 reviews)
"I really liked there was parking right there with the hotel, which made me feel safe, and I could come and go as I pleased. The room smelled fresh and clean as soon as we walked in. The staff was friendly and helpful with anything I needed. I would definitely stay here again!"

Reviewed on Mar. 24, 2025

Crowne Plaza Chicago West Loop by IHG
The Emily Hotel
The Emily Hotel
4 out of 5
311 North Morgan Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Apr. 20 to Apr. 21
CA $181
CA $213 total
includes taxes & fees
Apr 20 - Apr 21
9/10 Wonderful! (1,046 reviews)
7 women celebrating 70!
"Staff was very helpful and nice. Room was comfortable. Great shower and shower products."

Reviewed on Mar. 22, 2025

The Emily Hotel
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 $160 per night from Mar. 30 to Mar. 31
CA $160
CA $188 total
includes taxes & fees
Mar 30 - Mar 31
8/10 Very Good! (1,000 reviews)
"I liked the helpful people at the front desk."

Reviewed on Mar. 24, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
See all 4,261 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 $676, 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

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 $9
per traveller
Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour
Chicago: Fulton Market Donut Adventure with Tastings

Chicago: Fulton Market Donut Adventure with Tastings

CA $98
per adult
Chicago: Fulton Market Donut Adventure with Tastings
Marvels & Feats: An Engineer's Tour of Chicago Architecture

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

CA $50
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.