West Loop Vacations from ￥261,760

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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

The Latest West Loop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥320,168, price is now ￥261,760 per person
￥261,760
per person
Feb 19 - Feb 23
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Its room was perfect the only bad part was their was a couple stains in the bathroom wall

Reviewed on Dec 1, 2025

Chicago luxury home suites

Chicago luxury home suites

2 out of 5
Downtown Chicago
Price was ￥577,256, price is now ￥439,498 per person
￥439,498
per person
Feb 19 - Feb 23
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.

Reviewed on Nov 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥375,076, price is now ￥292,418 per person
￥292,418
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥350,800, price is now ￥277,580 per person
￥277,580
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.

Reviewed on Nov 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥379,200, price is now ￥302,369 per person
￥302,369
per person
Feb 21 - Feb 25
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.

Reviewed on Dec 1, 2025

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 showing a city

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 refundable
The price is ￥19,866 per night from Dec 21 to Dec 22
￥19,866
￥23,320 total
Dec 21 - Dec 22
includes taxes & fees
8.8/10 Excellent! (1,730 reviews)
Convenient location near family in the West Loop. Staff were efficient.

Reviewed on Nov 30, 2025

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
9/10 Wonderful! (1,278 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Get rates
The Emily Hotel
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
354 North Union Avenue Chicago IL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (355 reviews)
Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.

Reviewed on Nov 25, 2025

Get rates
Level Chicago Fulton Market
See all 4,813 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 ￥261,760, 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

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥7,083
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,866
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,296
per adult
92% of travellers recommend
Art Institute of Chicago
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.