Darien Vacations from $523

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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 $766, price is now $523 per person
$523
per person
Sep 3 - Sep 6
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Rooms were very old. There was blk mold or something in the shower. Window was broken too.

Reviewed on Jul 1, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $889, price is now $585 per person
$585
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
EXCELLENT , BREAKFAST AREA IS VERY GOOD AND THE JOURNEY IS AMAZING. ROOMS ARE COMPLETELY NEAT AND CONFORTABLE .HOTEL IS VERY WELL LOCATED .

Reviewed on Jun 30, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,376, price is now $926 per person
$926
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $801, price is now $542 per person
$542
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,105, price is now $754 per person
$754
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Muriel at the front desk made our 54th Anniversary memorable as she upgraded our room to a suite and sent a bottle of Prosecco and box of chocolates to our room plus a voucher for oysters at the restaurant. Kudos to her for being so kind and thoughtful. Thank you so much!!

Reviewed on Jun 30, 2026

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Stay near popular Darien attractions

National Shrine of St. Therese

7.4/10 (6 reviews)
This tranquil shrine houses the largest collection of St. Therese's personal effects outside France. Explore the museum's first-class relics and replica convent cell before reflecting in the serene garden sanctuary.
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What to do in Darien

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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
$149 nightly
The price is $177 total per night from Jul 2 to Jul 3
$177 total
Jul 2 - Jul 3
Total with taxes and fees
8/10 Very Good! (10,180 reviews)
"The rooms were clean and impressively spacious with beautiful views. I also thoroughly enjoyed dinner, which was both delicious and reasonably priced. The service throughout my stay was excellent."

Reviewed on Jul 1, 2026

Congress Plaza Hotel
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
$240 nightly
The price is $282 total per night from Jul 4 to Jul 5
$282 total
Jul 4 - Jul 5
Total with taxes and fees
8.4/10 Very Good! (2,332 reviews)
"Staff were really helpful and sweet during check in. During checkout I was told there are no shuttles to take me to my terminal in quite a short and ubrupt manner. But to be honest the price is ridiculous for the outdated hotel. Seems like they think they can charge Hilton prices for what looks like ..."

Reviewed on Jun 30, 2026

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Jul 20 to Jul 21
$154 total
Jul 20 - Jul 21
Total with taxes and fees
8.8/10 Excellent! (2,756 reviews)
"They over charge your card and then can’t tell what the charge is for or make something up. When we got there they gave us a dirty room and we had to call to get out room changed not a upgrade but whatever."

Reviewed on Jun 30, 2026

Hyatt Regency O'Hare Chicago
See all 3,807 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 $523 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.