West Town Vacations from $322
Book a Hotel + Flight or Car together to unlock savings
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.
Level Chicago – Old Town
Downtown Chicago
Price was $601, price is now $411 per person
$411
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Estuvo muy increíble, fue una experiencia maravillosa.Es un lugar precioso me encantó
Reviewed on Nov 1, 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.
West Town Hotel Deals
STAY
1415 Ashland Ave Chicago IL
$81 nightly
The price is $91 total per night from Nov 11 to Nov 12
$91 total
Nov 11 - Nov 12
Total with taxes and fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,090 reviews)
"Very nice historic hotel but there are little things that need attention such as the wallpaper by the 7th floor elevator. Other than that the room was clean and the staff provided quality customer service."
Reviewed on Nov 3, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 4 to Nov 5
$138 total
Nov 4 - Nov 5
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
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% 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.