Darien Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Darien Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Downtown Chicago
Price was CA $1,081, price is now CA $803 per person
CA $803
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,337 reviews)
Amazing room at a reasonable price! Great location and very friendly staff! Thank you to Jock, who made us feel welcome!

Reviewed on Jun 30, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,375, price is now CA $971 per person
CA $971
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Very clean, great location. Every staff member we encountered was just terrific

Reviewed on Jun 30, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,393, price is now CA $1,698 per person
CA $1,698
per person
Sep 1 - Sep 6
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,146, price is now CA $832 per person
CA $832
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very unique motif

Reviewed on Jul 1, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,615, price is now CA $1,205 per person
CA $1,205
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.

Reviewed on Jun 30, 2026

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Darien Hotel Deals

Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard Fontana WI
The price is CA $191 per night from Jul 7 to Jul 8
CA $191
CA $248 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (1,919 reviews)
"My kids send me love it for sure we coming back"

Reviewed on Jun 30, 2026

Abbey Resort and Avani Spa
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Jul 5 to Jul 6
CA $254
CA $320 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,356 reviews)
"Very comfortable bed. Room was large with microwave , fridge, sink and coffee maker. Balcony opened up to a great view of the lake. Great handmade bagel place right on the premises. Plenty of lunch and dinner spots close by. Be sure to book a cruise while you’re there. Short walk and plenty of ..."

Reviewed on Jun 30, 2026

Harbor Shores on Lake Geneva
Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
2400 E Geneva St Delavan WI
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jul 6 to Jul 7
CA $178
CA $246 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"Property was adequate. Don’t think I’d stay there again. There are newer hotels/resorts in the area."

Reviewed on Jun 29, 2026

Lake Lawn Resort
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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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Frequently asked questions

How much does a Darien vacation package cost?
You'll find cheap prices from CA $803 on Expedia for your Darien escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Darien costs.
What are the cheapest months to go to Darien?
If you're looking to book a cheap Darien vacation package, consider planning a trip in January, February and April. You'll generally find lower rates on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Darien?
With a well-planned itinerary, you can easily visit the main Darien sights in a few days. But if you'd like to discover hidden spots or take day trips, consider booking your Darien vacation for longer.
How to find the best Darien package deals?
Finding a cheap Darien package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Darien package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Darien vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Darien?
If you're considering a spur-of-the-moment Darien adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Darien?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Darien.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and activities. Your accommodations will likely be the biggest expense during your trip to Darien.
  3. Decide how long to go for: Now that you're up to speed on Darien, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your accommodations and airfare: After you've settled on your trip dates and duration, book the ideal Darien vacation package for you.

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.