West Loop Gate 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 Gate

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $747, price is now CA $442 per person
CA $442
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on Aug. 25, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,989, price is now CA $1,147 per person
CA $1,147
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,892, price is now CA $1,124 per person
CA $1,124
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on Aug. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,647, price is now CA $997 per person
CA $997
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,838, price is now CA $1,118 per person
CA $1,118
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

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
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 Gate Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Sep 1 to Sep 2
CA $208
CA $244 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,226 reviews)
"It was very close to navy pier where it was just a 10 min way. And had a great view from our room. Facing the lake"

Reviewed on Aug. 27, 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 1 to Sep 2
CA $186
CA $218 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,045 reviews)
"Very convenient to South Loop sites!"

Reviewed on Aug. 26, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 3 to Sep 4
CA $210
CA $246 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."

Reviewed on Aug. 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,641 properties in West Loop Gate
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 Gate vacation package cost?
Perhaps less than you imagined — from only CA $442, 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.

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 $10
per traveller
Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour
Bike or ebike Bar Hop - RiNo Arts District & Downtown

Bikes, Brews & Hidden Bars: A Ride Through RiNo & Downtown

CA $131
per adult
Bikes, Brews & Hidden Bars: A Ride Through RiNo & Downtown
Private Downtown Chicago TV and Movie Sites Guided Walking Tour

Private Downtown Chicago TV and Movie Sites Guided Walking Tour

CA $363
per adult
Private Downtown Chicago TV and Movie Sites Guided Walking Tour
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.