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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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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
Downtown Chicago
Price was CA $1,324, price is now CA $907 per person
CA $907
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8/10 Very good! (2,536 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,079, price is now CA $1,318 per person
CA $1,318
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Good property in a prime location

Reviewed on Nov 12, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.

Reviewed on Nov 13, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $1,944, price is now CA $1,379 per person
CA $1,379
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

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 $1,395, price is now CA $997 per person
CA $997
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

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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 $165 per night from Nov 24 to Nov 25
CA $165
CA $197 total
Nov 24 - Nov 25
includes taxes & fees
8/10 Very good! (10,070 reviews)
"Congress Plaza Hotel was an ideal hotel for its location to many Chicago sites. It is in walking distance to Soldier's Field which allowed us to get to the football game without dealing with traffic issues. Parking was easy to access and the lot was conveniently located behind the hotel."

Reviewed on Nov 13, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Dec 10 to Dec 11
CA $151
CA $180 total
Dec 10 - Dec 11
includes taxes & fees
River Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Nov 27 to Nov 28
CA $193
CA $271 total
Nov 27 - Nov 28
includes taxes & fees
Hilton Chicago
See all 3,814 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.
All Inclusive Vacations
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Stay near popular Darien attractions

National Shrine of St. Therese

7.4/10 (6 reviews)
You can spend an afternoon exploring the galleries in National Shrine of St. Therese in Darien. Wander the forest and lakeside in this trendy area.
See properties

What to do in Darien

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Darien

Frequently asked questions

How much does a Darien vacation package cost?
Offering great value package deals from CA $907 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.