
Boulder Hill Vacation Packages
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Top Boulder Hill Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $819, price is now CA $501 per person
CA $501
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Our experience here was fantastic. We visited in August and the weather was superb. Everything was centralized. From shopping to dining and peace and quiet were abound. Just magnificent stay. The staff was friendly and informative. Thank you.
Reviewed on Sep. 4, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,863, price is now CA $1,119 per person
CA $1,119
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service
Reviewed on Sep. 4, 2025

Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was CA $1,172, price is now CA $743 per person
CA $743
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
8.4/10 Very Good! (1,480 reviews)
Perfect area to walk around! Clean and easy to check in
Reviewed on Sep. 4, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,363, price is now CA $877 per person
CA $877
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (286 reviews)
The staff were excellent
Reviewed on Aug. 21, 2025
Boulder Hill Hotel Deals

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 $106 per night from Sep 8 to Sep 9
CA $106
CA $117 total
Sep 8 - Sep 9
includes taxes & fees

DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Sep 14 to Sep 15
CA $115
CA $128 total
Sep 14 - Sep 15
includes taxes & fees

Motel 6 Naperville, IL
1585 Naperville Wheaton Road, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $66 per night from Sep 15 to Sep 16
CA $66
CA $73 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.