Darien Holidays

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    Save up to NZ$616 when you book a flight and hotel together*
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Darien Holiday

Our pick of the best 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 NZ$495 per night from 7 Sept to 8 Sept
NZ$495
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,921 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"

Reviewed on 8 Aug. 2025

Congress Plaza Hotel
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
The price is NZ$384 per night from 21 Aug to 22 Aug
NZ$384
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (1,835 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."

Reviewed on 8 Aug. 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$302 per night from 24 Aug to 25 Aug
NZ$302
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (3,635 reviews)
"I liked the security and safeness. I did not like that there was no valet/door person to help with bags, when spending thousands of dollars I would expect a door person to be there to assist with bags out of car and up to room and would also appreciate complimentary water each day not 2 bottles in ..."

Reviewed on 8 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 3,770 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.

Discover the most popular places to visit in Darien

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Darien

River tour boat in Chicago

Architecture River Tour

NZ$69
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$75
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$67
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Darien

Frequently asked questions

How much does a Darien holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday 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 holiday package, consider travelling in April, July and November. You'll typically find lower prices on hotels and airfares during these months — ideal for budget-conscious travellers.
How many days is enough for Darien?
The ideal length for your Darien holiday 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 holiday package as early as possible.
Is it cheaper to book a Darien holiday as a package?
Expedia holiday 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 personalised Darien holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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 holiday.
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 personalised Darien holiday package.

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