West Loop Gate Vacation Packages

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Top Holiday Package Deals in West Loop Gate

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Price was CA $1,073, price is now CA $793 per person
CA $793
per person
Apr 28 - May 4
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
Everything was perfect and the front desk was so nice

Reviewed on Feb 10, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $2,409, price is now CA $1,720 per person
CA $1,720
per person
Apr 2 - Apr 6
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,154, price is now CA $851 per person
CA $851
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Housekeeper left hair shedding in room but overall amazing hotel and great staff

Reviewed on Feb 12, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,157, price is now CA $884 per person
CA $884
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Stay One Chicago

Stay One Chicago

2 out of 5
Downtown Chicago
Price was CA $3,061, price is now CA $2,385 per person
CA $2,385
per person
Apr 28 - May 4
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
No reviews
The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel". So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into. Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I). The app never worked, and we finally got physical key cards from the guy working for the building. There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced. I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.

Reviewed on Feb 10, 2026

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

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.

Find hotels in Downtown Chicago

West Loop Gate Hotel Deals

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 $121 per night from Feb 16 to Feb 17
CA $121
CA $142 total
Feb 16 - Feb 17
includes taxes & fees
8/10 Very Good! (9,863 reviews)
Good location for many activities. Room was good but less than great.

Reviewed on Feb 7, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Mar 4 to Mar 5
CA $162
CA $228 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,323 reviews)
Friendly staff, tasteful room

Reviewed on Feb 11, 2026

Hotel Riu Plaza Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Mar 7 to Mar 8
CA $267
CA $313 total
Mar 7 - Mar 8
includes taxes & fees
8.2/10 Very Good! (2,215 reviews)
A very good value. A bit worn, great bed but half the price of the Westin Denver airport.

Reviewed on Feb 8, 2026

Hilton Chicago O'Hare Airport
See all 4,725 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 $793, 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

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
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.