Darien Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Darien Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,118, price is now CA $768 per person
CA $768
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,895, price is now CA $1,259 per person
CA $1,259
per person
Jun 18 - Jun 21
found 16 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included
Reviewed on Apr 12, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,319, price is now CA $1,647 per person
CA $1,647
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!
Reviewed on Apr 13, 2026
Darien Hotel Deals
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Apr 19 to Apr 20
CA $144
CA $196 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (1,840 reviews)
The room was super clean .. the staff was also helpful and very friendly.. will definitely love to come back!
Reviewed on Apr 14, 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Apr 23 to Apr 24
CA $186
CA $262 total
Apr 23 - Apr 24
includes taxes & fees
8.6/10 Excellent! (3,217 reviews)
Beautiful property, stay was amazing from start to finish
Reviewed on Apr 13, 2026
The Cove Of Lake Geneva
111 Center St Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Apr 19 to Apr 20
CA $135
CA $188 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (1,436 reviews)
The rooms are a great size with everything you need. It's great walking distance to everything downtown. You can tell the property is a little older, but everything worked great and was cleaned well. I wish the bed was more confortable and it was less noisy, but overall i would recommend it
Reviewed on Apr 12, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
