A cityscape with tall buildings, a train track, and a snowy landscape.

West Loop Gate Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

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

The Latest West Loop Gate Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 24

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,780 reviews)
    "Great"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,306
    CA $975
    per traveller
    found 20 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,885 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,395
    CA $992
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 21 - Jan 24

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,801
    CA $1,316
    per traveller
    found 20 hours ago
    Park Hyatt Chicago
  • Jan 21 - Jan 24

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,344
    CA $984
    per traveller
    found 20 hours ago
    Pendry Chicago
  • Dec 31 - Jan 4

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (605 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,343
    CA $989
    per traveller
    found 4 hours ago
    Level Chicago Fulton Market

Where to stay in West Loop Gate

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

Downtown Chicago

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.

Discover the most popular places to visit in West Loop Gate

What to do near West Loop Gate

West Loop Gate Hotel Deals

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 Gate vacation package cost?

Perhaps less than you imagined — from only CA $975, in fact! By bundling flights, hotels and car rentals into your own custom-built package, your West Loop Gate escape is just a few clicks away.

How do I get a cheap travel package to West Loop Gate?

By bundling. Hotels, flights and rental cars — combine whatever you need into a West Loop Gate vacation package and save. Score even better deals when you add extras such as sightseeing tours to your booking. But that's not the only good part. You have the freedom to customize your vacation your way. We offer more than 550 airlines and 1,000,000 hotel options all over the world, so that everyone has an opportunity to travel and live out those vacation dreams.

Where should I stay in West Loop Gate?

Most visitors who travel to West Loop Gate include University of Illinois Chicago and United Center on their must-see lists. Why not consider a hotel close to one of these popular attractions?

What are the top hotels in West Loop Gate?

Hampton Inn Chicago Downtown West Loop and Homewood Suites by Hilton Chicago Downtown West Loop are among the most well-known properties in West Loop Gate. Why not check out the facilities and rates at each and then decide?

How far in advance should I book my West Loop Gate vacation?

Savvy travelers will likely want to reserve their seats early. You can normally look up international airfares on Expedia up to 12 months before your flight. If you're booking at the last minute, don't worry. Bargain prices occasionally become available just weeks before departure.

What does an Expedia West Loop Gate travel package include?

Travel packages include rental cars, hotels and flights, but you can mix and match them to create your dream West Loop Gate escape. You can also add on activities and tours once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll get access to discounts you won't find elsewhere.

What should I know before booking a West Loop Gate travel package?

Our prices are already low. However, you'll grab even more bargains if you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and tons of choice.

Can I choose my airline with a West Loop Gate Expedia vacation package?

Yes, you're in control. We offer more than 550 partner airlines worldwide, so you can design your West Loop Gate escape according to your travel needs.

If I'm not able to travel, can I cancel my West Loop Gate vacation package?

Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your West Loop Gate vacation package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may incur a charge from your hotel, airline or car rental company. For further information, visit our Customer Service Portal. We're here to help you each step of the way.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.