West Town Vacations from ￥337,288

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The Latest West Town Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥442,434, price is now ￥337,288 per person
￥337,288
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
Enjoyed our stay. Views were amazing and location convenient.

Reviewed on Mar 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥497,724, price is now ￥371,403 per person
￥371,403
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was perfect

Reviewed on Mar 27, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥437,268, price is now ￥349,207 per person
￥349,207
per person
May 14 - May 19
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent. Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value

Reviewed on Mar 24, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was ￥641,108, price is now ￥516,587 per person
￥516,587
per person
May 14 - May 19
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!

Reviewed on Mar 27, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was ￥475,226, price is now ￥383,552 per person
￥383,552
per person
May 14 - May 19
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on Mar 9, 2026

Where to stay in West Town

Find the best West Town areas and neighborhoods for the activities you enjoy most. Learn more about West Town
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 Town 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 ￥18,322 per night from Apr 5 to Apr 6
￥18,322
￥21,509 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (9,994 reviews)
Not much staff was apparent on the main floor throughout my stay. My initial encounter at check-in was with an unhelpful person but most of the staff was excellent. Instructions for the in-room coffee machine were not provided and I wasted the only coffee trying to work it. Walls were thin and adjacent ...

Reviewed on Mar 27, 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 ￥21,888 per night from Apr 9 to Apr 10
￥21,888
￥25,693 total
Apr 9 - Apr 10
includes taxes & fees
9/10 Wonderful! (3,991 reviews)
We had booked the lake view king suite room which the view was not great. When we got into the room it was very hot and we tried to turn the ac on but the air blowing out was still hot. Definitely would not book there again

Reviewed on Mar 27, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥23,357 per night from Apr 5 to Apr 6
￥23,357
￥27,419 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (5,779 reviews)
My kids loved the pool. The staff were very nice and friendly. We enjoyed the breakfast and happy hour. They made our room spotless and comfortable. We love our stay!

Reviewed on Mar 27, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,728 properties in West Town
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 Town vacation package cost?
Starting from as low as ￥337,288, you can customize your West Town package the way you want. Simply bundle hotels, flights and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to West Town?
Just think of all the thrilling things you could do in West Town with extra cash in your wallet. Watch your savings stack up when you combine your hotel and airfare bookings into a West Town vacation package. You have plenty of choice with Expedia too. In fact, you can choose from more than 550 air carriers and 1,000,000 hotel options worldwide. Whether you're taking off with the entire family or adventuring alone, exploring West Town is better with a package.
Where should I stay in West Town?
Visitors come from every corner of the globe to experience University of Illinois Chicago and United Center in West Town. Book a room close to these fantastic attractions to make sightseeing a breeze.
What are the top hotels in West Town?
If this will be your first time in West Town, book a room at Hyatt Place Chicago/Wicker Park or House Of Two Urns B&B. Both offer comfy beds and are popular options with many savvy travelers.
How far in advance should I book my West Town vacation?
Travelers can normally look up international fares on Expedia within 12 months of departure. Booking at the last minute? With a stroke of luck, it's still possible to nab a cheap ticket just weeks before your flight.
What does an Expedia West Town travel package include?
Hotels, car rentals and flights — we connect you to all the best deals. All you'll have to do is pick your favorite combination. After you've made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it easy to customize an amazing West Town vacation.
What should I know before booking a West Town travel package?
You'll pick up terrific savings when you bundle your flights, hotels and rental cars into a travel package. Plus, booking everything in one place will make your trip planning easier. So why waste your time or money? Whether you're organizing a luxury romantic escape or a budget family adventure, have a look at our package deals today.
Can I choose my airline with a West Town Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you definitely can. Simply pick your preferred air carrier and put together your ideal West Town vacation.
If I'm not able to travel, can I cancel my West Town vacation package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Locked in your West Town vacation package in the last 24 hours? You may be able to make changes for free. For bookings older than that, you may incur a charge from your hotel, airline or car rental company. For further information, take a look at our Customer Service Portal. We'll help you each step of the way.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,985
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,829
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,236
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.