West Loop 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

Top Holiday Package Deals in West Loop

Price found within the past 48 hours. Click for updated prices.
Freehand Chicago

Freehand Chicago

4 out of 5
Downtown Chicago
Price was CA $1,288, price is now CA $884 per person
CA $884
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
7.8/10 Good! (3,204 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,578, price is now CA $1,681 per person
CA $1,681
per person
Sep 5 - Sep 10
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities

Reviewed on Jul 30, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,207, price is now CA $1,450 per person
CA $1,450
per person
Sep 6 - Sep 11
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
A

Reviewed on Aug 2, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,563, price is now CA $1,032 per person
CA $1,032
per person
Oct 22 - Oct 25
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (540 reviews)
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,166, price is now CA $2,159 per person
CA $2,159
per person
Sep 12 - Sep 17
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

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
A busy city street with tall buildings, a bus, and cars.

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 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 refundable
The price is CA $339 per night from Aug 20 to Aug 21
CA $339
CA $403 total
Aug 20 - Aug 21
includes taxes & fees
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 refundable
The price is CA $292 per night from Aug 20 to Aug 21
CA $292
CA $364 total
Aug 20 - Aug 21
includes taxes & fees
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 $379 per night from Aug 30 to Aug 31
CA $379
CA $451 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,328 reviews)
"I love this place. The manager is so nice and I cannot wait to comeback and stay here again. The property is clean and modern. The hotel is also located close to a lot of restaurants and bars. My fiancé and I really enjoyed our stay."

Reviewed on Aug 1, 2026

The Emily Hotel
See all 4,572 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a West Loop vacation package cost?
Our West Loop packages, which start from just CA $884, 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.

Stay near popular West Loop attractions

Union Park

After visiting Union Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $71
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.