West Town Vacations from $418
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Your West Town Vacation
West Town is beckoning! Whatever type of getaway you have in mind, you can experience and see more of this neighborhood with a West Town vacation package. Your trip to West Town wouldn't be complete without a stop at major attractions nearby such as University of Illinois Chicago, United Center and Anna and Frederick Douglass Park. Don't just think about it — turn it into a reality! Lock in your ultimate West Town vacation with Expedia and experience travel your way.
The Latest West Town Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
$497
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Cet hôtel est tout simplement parfait. Tout est d'une propreté irréprochable, le buffet du matin compris dans le prix de la chambre est exceptionnel et varie tous les jours, Et que dire de l'emplacement, tout simplement idéal, au coeur de Chicago, au coin de selon moi la plus belle rue de Chicago le Michigan Avenue, à deux pas de la Chicago River. Je vous conseille fortement de faire le tour de bateau Architecture sur la rivière, c'est vraiment intéressant et ça va donnes une vue complètement différente de la ville. Chicago a été un énorme coup de cœur pour moi. Le seul bémol est que si vous y allez en vacances, mois ce fut pour affaire, prévoyez un budget car c'est assez dispendieux.
Reviewed on Oct 12, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$619
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 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.
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.
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.
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
$85 nightly
$94 total
Oct 20 - Oct 21
Total with taxes and fees
7.6/10 Good! (283 reviews)
"The first floor was pretty neat. The 2nd floor was actively under construction. There is not a patio seating, just construction materials. Place is recommended for young adults. You get what you paid for, which was fine for me. I only needed a bed and shower, don't forget to wear shower shoes."
Reviewed on Oct 10, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
$126 total
Nov 11 - Nov 12
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$144 nightly
$171 total
Oct 25 - Oct 26
Total with taxes and 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.
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 fascinating museums and acclaimed art scene in this vibrant area.
Photo by Chandan Rastogi
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.
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 fascinating museums in this vibrant area.
St. John Cantius Church
After visiting St. John Cantius Church, make a plan to see the other sights and activities in Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.
The Chop Shop & 1st Ward
You can enjoy a show at The Chop Shop & 1st Ward during your trip to Chicago. Experience the live music and theater scene in this vibrant area.
The Den Theatre
After visiting The Den Theatre, make a plan to see the other sights and activities in Chicago. Experience the live music and theater scene in this vibrant area.
House Theatre
You can make plans for a show at House Theatre on your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.