Darien Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,207, price is now CA $798 per person
CA $798
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
everyone at the front desk was helpful and quite nice. room and amenities very clean. gym was well done for such a small space. would be great if there was a bathroom there. coffee and fresh fuit in the morning was awesome.
Reviewed on Jun 19, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,758, price is now CA $1,194 per person
CA $1,194
per person
Sep 10 - Sep 14
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.
Reviewed on Jun 20, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,439, price is now CA $1,687 per person
CA $1,687
per person
Sep 14 - Sep 17
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Usually this is one of the best property but this time they had water pipe burst and elevators werent working because of that. It was very inconvinient for this stay.
Reviewed on Jun 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,746, price is now CA $1,217 per person
CA $1,217
per person
Sep 14 - Sep 17
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Darien Hotel Deals
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Jun 23 to Jun 24
CA $253
CA $319 total
Jun 23 - Jun 24
includes taxes & fees
9.2/10 Wonderful! (1,351 reviews)
"Excellent view of the lake from the balcony. Some parts, recently painted and updated. Comfortable room and beds. Good shower pressure. Clean, some parts dated."
Reviewed on Jun 21, 2026
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Jun 28 to Jun 29
CA $192
CA $250 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,914 reviews)
"Perfect location. The room was a little run down but all-in-all I had a great stay at a great location."
Reviewed on Jun 21, 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Jul 7 to Jul 8
CA $343
CA $438 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (3,292 reviews)
"Our room was great and very clean! The staff was so nice and was great with my toddler. Waterpark was amazing for my little one!"
Reviewed on Jun 20, 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.
