West Town Vacation Packages
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Top Holiday Package Deals in West Town
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.
Reviewed on Nov 13, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,057, price is now CA $2,112 per person
CA $2,112
per person
Dec 28 - Jan 2
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 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
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
West Town Hotel Deals
STAY
1415 Ashland Ave Chicago IL
The price is CA $49 per night from Dec 9 to Dec 10
CA $49
CA $133 total
Dec 9 - Dec 10
includes taxes & fees
7.6/10 Good! (299 reviews)
"Not what it seems, consider staying away from this business — Everything seemed great at first, but after a few days, some staff members completely switched up out of nowhere and became extremely rude, lied, and unprofessional. My boundaries were crossed. So disappointing really. A staff member bolted ..."
Reviewed on Nov 13, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 23 to Nov 24
CA $166
CA $197 total
Nov 23 - Nov 24
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Dec 1 to Dec 2
CA $165
CA $197 total
Dec 1 - Dec 2
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
Stay near popular West Town attractions
Things to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Chicago By Night River and Lake Cruise
CA $71
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.