Darien Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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Better together
Save up to CA $1,096 when you book a flight and hotel together*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Darien Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,309, price is now CA $837 per person
CA $837
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug. 21, 2025
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,197, price is now CA $1,334 per person
CA $1,334
per person
Nov 5 - Nov 8
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
Arlo Chicago
Downtown Chicago
Price was CA $1,416, price is now CA $905 per person
CA $905
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,844 reviews)
Good spot, convenient to everything. Staff was helpful. Very urban so some issues with people begging for money etc.
Reviewed on Sep. 3, 2025
Level Chicago - River North
Downtown Chicago
Price was CA $1,489, price is now CA $964 per person
CA $964
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (672 reviews)
Loved my stay here, beautiful hotel, great amenities, friendly staff super accommodating
Reviewed on Sep. 1, 2025
Darien Hotel Deals
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Oct 1 to Oct 2
CA $209
CA $285 total
Oct 1 - Oct 2
includes taxes & fees
Abbey Resort and Avani Spa
269 Fontana Boulevard, Fontana, WI
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Sep 7 to Sep 8
CA $135
CA $184 total
Sep 7 - Sep 8
includes taxes & fees
Harbor Shores on Lake Geneva
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Sep 11 to Sep 12
CA $183
CA $236 total
Sep 11 - Sep 12
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.
