Boulder Hill Vacation Packages
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Top Boulder Hill Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,066, price is now CA $1,229 per person
CA $1,229
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug. 29, 2025
Pendry Chicago
Downtown Chicago
Price was CA $1,375, price is now CA $820 per person
CA $820
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.
Reviewed on Aug. 26, 2025
The Emily Hotel
Downtown Chicago
Price was CA $2,190, price is now CA $1,400 per person
CA $1,400
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug. 22, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,133, price is now CA $740 per person
CA $740
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (282 reviews)
The staff were excellent
Reviewed on Aug. 21, 2025
Boulder Hill Hotel Deals
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Sep 7 to Sep 8
CA $114
CA $127 total
Sep 7 - Sep 8
includes taxes & fees
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Sep 16 to Sep 17
CA $98
CA $109 total
Sep 16 - Sep 17
includes taxes & fees
Motel 6 Naperville, IL
1585 Naperville Wheaton Road, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $72 per night from Sep 15 to Sep 16
CA $72
CA $80 total
Sep 15 - Sep 16
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.
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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.