Darien Vacations from $630

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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 $910, price is now $630 per person
$630
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back up to the room Other than that the front desk and cleaning ladies was very nice.

Reviewed on May 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,291, price is now $823 per person
$823
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Staff was amazing and the apartment building was phenomenally clean!

Reviewed on May 28, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,049, price is now $681 per person
$681
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
Hotel room was very neat and clean. The continental breakfast on the second floor was fantastic and had a vast variety of breakfast food to choose from. For the amount of food and people for this room, the staff did an excellent job keeping this cleaned and very well maintained. Upon checking in and checking out, the staff was very warm and friendly. The customer service was top-notch. Would recommend to anyone staying in Chicago to stay here!

Reviewed on May 30, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,114, price is now $739 per person
$739
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
Staff was so helpful

Reviewed on May 29, 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
Save 100% on your flight
Price was $1,161, price is now $778 per person
$778
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.

Reviewed on May 28, 2026

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Discover the most popular places to visit in Darien

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
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

4.5/5(336 reviews)

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

What to do in Darien

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
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
96% 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
$140 nightly
The price is $166 total per night from Jun 29 to Jun 30
$166 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,135 reviews)
"The room was small and was missing modern convinces-microwave-better seating space. The staff were friendly and the restaurant was great! I only wished we had gotten a better room! Special shout out to Steve P. the doorman for his service and friendly demeanor!!"

Reviewed on May 30, 2026

Congress Plaza Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $207 total per night from Jun 29 to Jun 30
$207 total
Jun 29 - Jun 30
Total with taxes and fees
Hotel Felix River North/Magnificent Mile
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $190 total per night from Jun 29 to Jun 30
$190 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (3,040 reviews)
"Overall, we had a good stay at the Freehand Chicago. The location was convenient, and despite being in a busy area, we slept peacefully throughout the night. The hotel was also accommodating in holding our luggage after checkout since we had a later flight, which we appreciated. That said, there ..."

Reviewed on May 30, 2026

Freehand Chicago
See all 3,945 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 $630 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.