West Loop Gate Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in West Loop Gate

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,271, price is now CA $892 per person
CA $892
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
The hotel is fresh and clean. Very nice facility. Staff anre wonderful. Only comment is there should be free water in the rooms, at least for Marriott members. For the rates charged, water should be included. Water pressure is a bit low.

Reviewed on Jun 21, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,474, price is now CA $997 per person
CA $997
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Overall, the hotel was okay for the price, but pretty basic. The room was very simple and lacked some expected amenities—there were no slippers provided, which was a bit disappointing. Also, the area around the bed wasn’t very clean, which affected the overall experience. I paid $170 per night, and for that price, I expected a bit more attention to cleanliness and comfort. It’s not terrible, but definitely not great either.

Reviewed on Jun 22, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,871, price is now CA $1,383 per person
CA $1,383
per person
Aug 15 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,850, price is now CA $1,372 per person
CA $1,372
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views

Reviewed on Jun 22, 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was CA $1,290, price is now CA $958 per person
CA $958
per person
Sep 14 - Sep 17
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (622 reviews)
James at the front desk was absolutely incredible. It was a quick stay due to storms in the area, but James' professionalism and care added some positivity to an otherwise stressful travel experience.

Reviewed on Jun 22, 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

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

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 $193 per night from Jun 29 to Jun 30
CA $193
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,167 reviews)
"Room smelled a little like mold or sitting water although the floors were never and the room was clear overall. The shower had a lot of rust in it. Hotel does not offer parking and the garage they recommend is was already full."

Reviewed on Jun 23, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Jul 7 to Jul 8
CA $197
CA $235 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (4,465 reviews)
"Great location, rooms and service"

Reviewed on Jun 23, 2026

Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jun 29 to Jun 30
CA $178
CA $211 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,615 reviews)
"Stunning room, lobby, and spectacular views from the rooftop lounge. That being said, room service could’ve been more attentive. We asked for body wash for our room, as it was out when we checked in. Even after calling the front desk, this small request went unanswered. Barring that, it was a good ..."

Reviewed on Jun 23, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,584 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.
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Frequently asked questions

How much does a West Loop Gate vacation package cost?
Perhaps less than you imagined — from only CA $892, 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $69
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
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.