West Loop Vacations from ￥290,398

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    Save up to ￥109,000 when you book a flight and hotel together*

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The Latest West Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
Price was ￥322,136, price is now ￥290,398 per person
￥290,398
per person
Jan 11 - Jan 18
found 22 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.8/10 Excellent! (2,073 reviews)

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Price was ￥350,558, price is now ￥299,844 per person
￥299,844
per person
Jan 11 - Jan 18
found 22 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,106 reviews)
A very nice stay!!! It was exactly what we were looking for. The staff were friendly and helpful!!!

Reviewed on Nov 10, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was ￥336,668, price is now ￥291,983 per person
￥291,983
per person
Jan 11 - Jan 18
found 22 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (3,188 reviews)

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was ￥336,504, price is now ￥295,403 per person
￥295,403
per person
Jan 11 - Jan 18
found 22 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Great stay, zero complaints!

Reviewed on Nov 10, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was ￥333,890, price is now ￥297,020 per person
￥297,020
per person
Jan 11 - Jan 18
found 22 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.6/10 Excellent! (2,885 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 cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

West Loop Hotel Deals

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 ￥15,959 per night from Nov 23 to Nov 24
￥15,959
￥20,871 total
Nov 23 - Nov 24
includes taxes & fees
8.6/10 Excellent! (1,274 reviews)
"Great service"

Reviewed on Nov 10, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
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 ￥18,171 per night from Nov 22 to Nov 23
￥18,171
￥21,606 total
Nov 22 - Nov 23
includes taxes & fees
9/10 Wonderful! (2,817 reviews)
"Great location for a stay in the west loop..good for solo travelers.."

Reviewed on Nov 10, 2026

Crowne Plaza Chicago West Loop 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 ￥31,009 per night from Nov 24 to Nov 25
￥31,009
￥36,866 total
Nov 24 - Nov 25
includes taxes & fees
The Emily Hotel
See all 4,556 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.

Frequently asked questions

How much does a West Loop vacation package cost?
Our West Loop packages, which start from just ￥290,398, 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

￥3,809
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,269
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

￥6,636
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.