Darien Vacations

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Darien Vacation Packages

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 ₩161,507 per night from Jul 7 to Jul 8
₩161,507
₩189,593 total
Jul 7 - Jul 8
includes taxes & fees
7.8/10 Good! (8,952 reviews)
"The location is amazing. Every staff member i had an encounter with was very kind and courteous. The elevators are amazing for an older hotel. So fast and efficient. This was our second stay there. When we go back to Chicago I plan on staying here."

Reviewed on Jul 3, 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
The price is ₩249,010 per night from Jul 9 to Jul 10
₩249,010
₩292,313 total
Jul 9 - Jul 10
includes taxes & fees
8.4/10 Very Good! (4,326 reviews)
"Awesome"

Reviewed on Jul 3, 2025

Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩183,308 per night from Jul 7 to Jul 8
₩183,308
₩215,185 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (3,271 reviews)
"Perfect stay and great customer service"

Reviewed on Jul 3, 2025

citizenM Chicago Downtown
See all 3,622 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.

Frequently asked questions

How much does a Darien vacation package cost?
You can snap up a vacation package to this destination 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'd like to snag a cheap Darien vacation package, consider traveling in April, July and November. You'll typically find lower prices on hotels and airfares during these months --- ideal for budget-conscious travelers.
How many days is enough for Darien?
The ideal length for your Darien vacation depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to check out all the top attractions and discover some hidden treasures along the way.
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.
How to plan a trip to Darien?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Darien.
  2. Set your budget: Factor in expenses like food, flights and transportation when calculating how much to save for your trip to Darien. Then, choose a property that fits your budget, whether that's an affordable option or a more upscale getaway.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in Darien. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Darien vacation package.

Discover the most popular places to visit in Darien

Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.