West Loop 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

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,207, price is now CA $798 per person
CA $798
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
everyone at the front desk was helpful and quite nice. room and amenities very clean. gym was well done for such a small space. would be great if there was a bathroom there. coffee and fresh fuit in the morning was awesome.

Reviewed on Jun 19, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,758, price is now CA $1,194 per person
CA $1,194
per person
Sep 10 - Sep 14
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.

Reviewed on Jun 20, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,439, price is now CA $1,687 per person
CA $1,687
per person
Sep 14 - Sep 17
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Usually this is one of the best property but this time they had water pipe burst and elevators werent working because of that. It was very inconvinient for this stay.

Reviewed on Jun 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,746, price is now CA $1,217 per person
CA $1,217
per person
Sep 14 - Sep 17
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,476, price is now CA $1,074 per person
CA $1,074
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,799 reviews)
very clean and friendly staff

Reviewed on Jun 18, 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

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 Hotel Deals

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Jul 1 to Jul 2
CA $246
CA $292 total
Jul 1 - Jul 2
includes taxes & fees
9/10 Wonderful! (2,269 reviews)
"Everything was nice"

Reviewed on Jun 20, 2026

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Jul 1 to Jul 2
CA $211
CA $268 total
Jul 1 - Jul 2
includes taxes & fees
8.8/10 Excellent! (1,036 reviews)
"The pool was clean but very cold. The room was old and dirty for $450 a night. Which is already insane for a holiday inn. Our bed had pen marks all over it, the carpet was extremely frayed. We were placed right next to a loud elevator where you could hear everything. The “manager” called the day ..."

Reviewed on Jun 20, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $347 per night from Jun 28 to Jun 29
CA $347
CA $413 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (1,319 reviews)
"Close to a ton of great dining options. Nice staff"

Reviewed on Jun 20, 2026

The Emily Hotel
See all 4,752 properties in West Loop
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 vacation package cost?
Our West Loop packages, which start from just CA $798, 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.

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 Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and 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.