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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,916, price is now CA $1,246 per person
CA $1,246
per person
Jun 11 - Jun 15
found 5 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Hard to find the parking . Everything at navy pier closes at 8pm . Staff offered no extras even though it says we are vip Expedia and hiltons honors .
Reviewed on Apr 17, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,268, price is now CA $1,580 per person
CA $1,580
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,622, price is now CA $1,830 per person
CA $1,830
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
Celebrate my birthday here and upon arrival was given champagne. It made my evening even better. I felt at home will be returning
Reviewed on Apr 18, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,526, price is now CA $1,069 per person
CA $1,069
per person
Jun 11 - Jun 15
found 5 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on Apr 14, 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
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.
West Town Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from May 10 to May 11
CA $190
CA $226 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (4,152 reviews)
When I looked around the hotels near this one were several times more expensive…ie, The Four Seasons is very close by. While we know that’s a huge upgrade, the Hilton was clean, friendly and in a great location. We came back to sleep! The rooms are dated, but ours separated the king sized “bedroom” ...
Reviewed on Apr 18, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Apr 26 to Apr 27
CA $213
CA $250 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (5,859 reviews)
Clean and easy check in.
Reviewed on Apr 17, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Apr 26 to Apr 27
CA $158
CA $185 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,139 reviews)
The hotel is opposite an above ground train and so there’s significant outdoor noise at night if you’re facing that side of the hotel.
Reviewed on Apr 18, 2026
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
Things to do
Skydeck - Willis Tower Admission
CA $60
per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.