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 $1,134, price is now CA $732 per person
CA $732
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,131 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 $1,780, price is now CA $1,054 per person
CA $1,054
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,882 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! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.
Reviewed on Apr 27, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,140, price is now CA $1,398 per person
CA $1,398
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,745, price is now CA $1,144 per person
CA $1,144
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,458 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 14 to May 15
CA $80
CA $90 total
May 14 - May 15
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 21 to May 22
CA $144
CA $187 total
May 21 - May 22
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 $166 per night from May 14 to May 15
CA $166
CA $187 total
May 14 - May 15
includes taxes & fees
8.6/10 Excellent! (1,023 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.
