Darien Vacation Packages

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Your Darien Vacation

There's tons to love about Darien, from its rich history to its spectacular views. When you're ready to spend some time in this captivating city, our Darien vacation packages will be perfect for you. If your trip to Darien includes some sightseeing, hit up well-known attractions like Morton Arboretum, Promenade Bolingbrook and Cog Hill Golf & Country Club. Whatever your travel plans or budget, organizing a tailored Darien vacation is easy with Expedia.

Top Darien Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,139 reviews)
The view @ location was amazing!!!!

Reviewed on Aug. 3, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 8 - Sep 11
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on Jul. 26, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Very friendly staff!

Reviewed on Aug. 3, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,922 reviews)
We spent 4 nights and had no major complaints. I don't understand why there was an additional mandatory destination fee for normal amenities that we did not ask for or use.

Reviewed on Aug. 1, 2025

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Darien Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,940 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug. 1, 2025

Congress Plaza Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,335 reviews)
"Thanks beautiful place"

Reviewed on Aug. 3, 2025

Crowne Plaza Chicago West Loop by IHG
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Aug 24 to Aug 25
CA $240
CA $281 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (4,599 reviews)
"Ok"

Reviewed on Aug. 2, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 3,756 properties in Darien
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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Discover the most popular places to visit in Darien

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Darien

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Darien

Frequently asked questions

How much does a Darien vacation package cost?
Offering great value package deals from CA $1,010 on Expedia, you'll be surprised at how little a vacation to Darien costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Darien?
You can usually find reduced prices and better availability in April, July and November. Browse our cheap Darien vacation packages and you could get some excellent off-season deals.
How many days is enough for Darien?
We'd suggest booking a Darien vacation for at least 3 days. This will allow you time to tick off popular sights such as Seven Bridges Golf Club and Mayslake Peabody Mansion, as well as check out neighbourhoods like Clarendon Hills and Indian Head Park. You could even squeeze in one or two day trips from Darien.
How to find the best Darien package deals?
Use Expedia's filter tool to help you find some of the best Darien package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Darien package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still get the freedom to create a customized Darien vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Darien?
If you've got your Darien travel dates confirmed, book as early as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Darien?

  1. Choose your travel dates: The things you'd like to do in Darien and your favourite season can help you decide when to go.
  2. Set your budget: Consider expenses like food, flights and transportation when working out how much to save for your trip to Darien. Then, pick a hotel that matches your budget, whether that's a low-cost option or a lavish getaway.
  3. Decide how long to go away for: Now that you're up to speed on Darien, you can figure out the ideal length of your break. Pull together a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the ideal Darien vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.