Manhattan Vacation Packages
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Top Manhattan Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,388, price is now CA $874 per person
CA $874
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on Apr 24, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $2,127, price is now CA $1,251 per person
CA $1,251
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.4/10 Very Good! (1,891 reviews)
The HVAC was annoying AF. It would go on and blow cold air for 10 minutes, then be off for 15-20 minutes repeatedly. It is so loud, it kept waking me up through out the night. As a short person, I did not like the fact the bed was a challenge to get on top. Not everyone is five feet tall.
Reviewed on Apr 26, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,399, price is now CA $879 per person
CA $879
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.
Reviewed on Apr 27, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,713, price is now CA $1,106 per person
CA $1,106
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place
Reviewed on Apr 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,813, price is now CA $1,183 per person
CA $1,183
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Great week-long stay. We loved the king corner room - the views were fantastic. Room was large and comfortable. All staff were really accommodating.
Reviewed on Apr 29, 2026
Manhattan Hotel Deals
Econo Lodge South Holland - Chicago Southland
17301 S Halsted St, Building B South Holland IL
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from May 17 to May 18
CA $80
CA $90 total
May 17 - May 18
includes taxes & fees
6/10 (768 reviews)
The king size bed is very comfortable
Reviewed on Apr 28, 2026
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
The price is CA $144 per night from May 13 to May 14
CA $144
CA $187 total
May 13 - May 14
includes taxes & fees
8.6/10 Excellent! (1,487 reviews)
Nice experience
Reviewed on Apr 28, 2026
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from May 14 to May 15
CA $169
CA $191 total
May 14 - May 15
includes taxes & fees
8.6/10 Excellent! (1,024 reviews)
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Reviewed on Apr 27, 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.
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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.
