Darien Vacations from $272

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
Save 100% on your flight
Price was $415, price is now $272 per person
$272
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (565 reviews)
Convenient and clean

Reviewed on Aug 22, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
Price was $600, price is now $336 per person
$336
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,288 reviews)
Chip painting in shower/tub

Reviewed on Aug 22, 2025

Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Save 100% on your flight
Price was $724, price is now $420 per person
$420
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,002 reviews)
⭐️⭐️⭐️⭐️⭐️ Hotel Review: Hyatt Regency Deerfield I stayed at the Hyatt Regency Deerfield from Friday to Sunday, and it was truly a wonderful experience! The rooms were cozy, spotless, and very comfortable, making it easy to relax after a busy weekend. The staff was exceptional—warm, welcoming, and attentive in every interaction. The dining facility was excellent, with both the food and service exceeding expectations. After attending the John Legend concert, returning to the hotel felt like coming to a home away from home. Kudos to the entire team at Hyatt Regency Deerfield for making the stay memorable. I’ll definitely return and highly recommend this hotel!

Reviewed on Aug 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,695, price is now $1,042 per person
$1,042
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
Had a great experience. Clean room, great rooftop bar, great breakfast!

Reviewed on Aug 25, 2025

Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Half Day
Save 100% on your flight
Price was $494, price is now $313 per person
$313
per person
Oct 31 - Nov 5
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
In a great neighborhood. Quiet, clean. Excellent room layout. Free laundry was very nice to have. Nice breakfast.

Reviewed on Aug 14, 2025

Don't see what you're looking for?
See all available trips from Columbus to Darien
View all trips

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
Magnificent Mile - River North showing night scenes, a city and signage

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

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
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 Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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
$153 nightly
The price is $180 total per night from Sep 1 to Sep 2
$180 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (9,016 reviews)
"I really enjoyed my stay here . The hotel is very historical and is known for hosting beautiful weddings, it’s huge , restaurants on property, and is very close to everything there is to see in downtown Chicago . Very close to the river walk , millennium park, coffee shops/breakfast, the loop , Taco ..."

Reviewed on Aug 25, 2025

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
$152 nightly
The price is $179 total per night from Sep 3 to Sep 4
$179 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,765 reviews)
"Everyone was very helpful and polite. The room was clean and spacious. My kids loved the breakfast and snacks at night."

Reviewed on Aug 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $229 total per night from Sep 2 to Sep 3
$229 total
Sep 2 - Sep 3
Total with taxes and fees
8.4/10 Very Good! (1,888 reviews)
"Customer service amazing"

Reviewed on Aug 24, 2025

Palmer House a Hilton Hotel
See all 3,815 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Darien vacation package cost?
You can snap up a vacation package to this destination from $272 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

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.