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.
The Talbott, Autograph Collection
Downtown Chicago
CA $860
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
It’a a beautiful and charming building with just the right amount of modernity.
My room was a tad bit smalller than I’d expected (queen bed) and the view was nonexistent but cozy and comfortable for for a single person. The room came with a fully stocked mini fridge, a Nespresso
machine and two very plush bath robes.
The staff was very accommodating and friendly. Each day I was there(three), housekeeping was excellent
Shopping, dining and spectacular architecture are in ample supply right outside your door. Will definitely stay here when I’m there city!
Reviewed on Oct 26, 2026
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
4 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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
West Loop Hotel Deals
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
CA $137
CA $180 total
Nov 24 - Nov 25
includes taxes & fees
8.6/10 Excellent! (1,261 reviews)
"."
Reviewed on Oct 26, 2026
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundable
CA $175
CA $208 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (2,758 reviews)
"Very comfy bed and easy to adjust the temp of the room! Stayed here for a weekend in Chicago and it was an easy walk to West Loop amenities."
Reviewed on Oct 26, 2026
The Emily Hotel
311 North Morgan Street Chicago IL
CA $269
CA $320 total
Nov 22 - Nov 23
includes taxes & fees
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.
Frequently asked questions
How much does a West Loop vacation package cost?
Our West Loop packages, which start from just CA $770, 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.
Stay near popular West Loop attractions
Union Park
After visiting Union Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
The Old Post Office
You can find out about the history of Chicago with a stop at The Old Post Office. Discover the entertainment choices and notable monuments in this vibrant area.
Garcia's Chicago
Garcia's Chicago is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or visit the notable monuments in this vibrant area.
Old St Patrick’s Church
Learn about the local history of Chicago with a stop at Old St Patrick’s Church. Discover the acclaimed art scene and notable monuments in this vibrant area.
Randolph Street Market
Enjoy an outing to Randolph Street Market during your stay in Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
The Empty Bottle
The Empty Bottle is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's riverfront or experience its acclaimed art scene.
City Winery
You can enjoy a show at City Winery during your trip to Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
Packer Schopf Gallery
You can spend time browsing the exhibits at Packer Schopf Gallery in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Things to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.