West Loop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
Staff was great, very attentive.

Reviewed on Jul. 14, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on Jul. 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 14 - Aug 18
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Hotel is beautiful! Staff was amazing! It was super clean, and the buffet was to die for! However, the wifi did not work! I needed it to do work on my computer and I couldn’t do anything!

Reviewed on Jul. 14, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 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 $202 per night from Aug 10 to Aug 11
CA $202
CA $237 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,261 reviews)
Salt Shed hotel stay
"We had a pleasant stay at the Crowne Plaza Chicago West, parking was a bit more expensive but definitely convenient. Room was nice and clean."

Reviewed on Jul. 14, 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 $207 per night from Aug 10 to Aug 11
CA $207
CA $260 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
Great stay!
"It was excellent. Our tv in the living room area did not work. I contacted the hotel through a text service and it was immediately fixed. Great hotel, great service and love the rooftop pool on the penthouse level!"

Reviewed on Jul. 14, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street, Chicago, IL
The price is CA $220 per night from Jul 27 to Jul 28
CA $220
CA $258 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,122 reviews)
"Spacious room with a very comfortable bed, comfortable room temperature on a hot weekend, large bathroom and spacious work station. Close to trains that transport to the loop within minutes."

Reviewed on Jul. 8, 2025

The Emily Hotel
See all 4,559 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 $753, 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 $92
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.