West Town Vacations from ￥286,880
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The Latest West Town Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥642,213
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,348 reviews)
A lot of junk fees parking horrible so valet 89 dollars a night hotel was clean but the area was not good for downtown homeless people everywhere restaurants close at 9 pm on weekends and traffic so bad u have to uber everywhere and valet I booked this room for 2 days for a concert wanted the best but was not the best location for 750 for 2 nights everywhere we went we had to uber their and back
Reviewed on Aug 24, 2026
The Peninsula Chicago
Downtown Chicago
￥462,080
per person
Nov 17 - Nov 22
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
First time staying at this
Property and we absolutely loved it! Will definitely go back and recommend
Reviewed on Aug 23, 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
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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
West Town Hotel Deals
STAY
1415 Ashland Ave Chicago IL
￥6,644
￥16,479 total
Sep 23 - Sep 24
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,962
￥20,168 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very Good! (10,304 reviews)
"Lovely stay, beautiful architecture"
Reviewed on Aug 24, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥22,725
￥27,018 total
Aug 25 - Aug 26
includes taxes & fees
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 ￥286,880, 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.
Stay near popular West Town attractions
Humboldt Park
7.0/10 (2 reviews)
Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theater scene and fascinating museums in this vibrant area.
Milwaukee Avenue
You can enjoy retail therapy at Milwaukee Avenue during your visit to Chicago. Experience the live music and theater scene in this vibrant area.
The Salt Shed
You can get tickets for a performance at The Salt Shed during your stay in Chicago. Experience the live music and theater scene in this vibrant area.
Subterranean
You can enjoy a show at Subterranean during your stay in Chicago. Experience the live music and theater scene in this vibrant area.
Intuit: The Center for Intuitive and Outsider Art
Enjoy a stop at Intuit: The Center for Intuitive and Outsider Art, an entertaining place to visit in Chicago. Amble around this vibrant area's riverfront or experience its acclaimed art scene.
Polish Museum of America
You can spend time studying the exhibits at Polish Museum of America during your travels in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.
St. John Cantius Church
After visiting St. John Cantius Church, make a plan to see the other sights and activities in Chicago. Experience the fascinating museums and entertainment choices in this vibrant area.
Chopin Theatre-Death and Harry Houdini
You can get tickets for a performance at Chopin Theatre-Death and Harry Houdini during your stay in Chicago. Experience the acclaimed theater scene and entertainment choices in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.