Darien Vacations from $657

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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.

The Latest Darien vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $974, price is now $657 per person
$657
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The property looks beautiful and the staff is very friendly. The details are, however, very lacking. The window in my room was drafty and upon inspection there were stains on the curtains. The shower had basically no edge to it and the curtain was short enough that the floor flooded when we showered. The bed was also not comfortable- especially the pillows which had zero support. It's a good location but I definitely won't be staying here again.

Reviewed on Mar 19, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,377, price is now $803 per person
$803
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.

Reviewed on Mar 20, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,451, price is now $890 per person
$890
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Great experience overall. TV streaming apps would not connect to the internet even after engineering came by to try to fix it.

Reviewed on Mar 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,575, price is now $997 per person
$997
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer

Reviewed on Mar 17, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,182, price is now $800 per person
$800
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room

Reviewed on Mar 20, 2026

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Discover the most popular places to visit in Darien

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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 featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Darien

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$26
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

$40
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Darien

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
$116 nightly
The price is $136 total per night from Apr 1 to Apr 2
$136 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,977 reviews)
Overall, the hotel was clean, and the lounge was spacious, well-organized, and inviting. The property is a bit older, but not in a negative way—it simply has that classic feel. Our room was on the 5th floor, and the area was quiet, which made our stay very comfortable. The location is also excellent. ...

Reviewed on Mar 21, 2026

Congress Plaza Hotel
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
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (5,757 reviews)
Hotel is conveniently located, clean and rooms were spacious. Evening reception and breakfast selections are fantastic. The only downside was the pool area is small with limited seating but the kiddos still enjoyed. Staff was very professional and helpful. Would stay again.

Reviewed on Mar 20, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $259 total per night from Apr 12 to Apr 13
$259 total
Apr 12 - Apr 13
Total with taxes and fees
8.4/10 Very Good! (2,230 reviews)
The hotel had no electricity upon arrival, inexplicably as there were no severe weather conditions. I was handed two glow sticks to be able to guide my way around the hotel and my room. You can’t make this stuff up. The fact that there was nothing provided to compensate for the matter (discount, ...

Reviewed on Mar 19, 2026

Hilton Chicago O'Hare Airport
See all 3,902 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.

Find the Best Darien Vacation Packages

Darien Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
22,300
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brookfield Zoo, Galloping Ghost and DuPage Childrens Museum

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Frequently asked questions

How much does a Darien vacation package cost?
You can snap up a vacation package to this destination from $657 on Expedia. However, how much your vacation to Darien costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Darien?
If you're looking to book a cheap Darien vacation package, consider visiting in January, June and August. You'll typically find better prices on flights and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Darien?
With a well-organized schedule, you can easily hit the top Darien attractions in a few days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Darien vacation for longer.
How to find the best Darien package deals?
Use Expedia's handy filters to help you find some of the best Darien package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Darien package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Darien vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Darien?
Secure incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Darien vacation.
Does Expedia offer Book Now, Pay Later Darien vacation packages?
Set off on your dream trip to Darien with our Book Now, Pay Later vacations. There's no need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up bargains while they last.

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.