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Darien Holidays from £804

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Your Darien Holiday

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 holiday 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, organising a tailored Darien holiday is easy with Expedia.

Top Darien flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 25 Dec - 30 Dec

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,581 reviews)
    "All good"
    Reviewed November 12, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,007
    £804
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • 25 Dec - 30 Dec

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,073 reviews)
    "i love it"
    Reviewed November 10, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,790
    £1,319
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 20 Jan - 26 Jan

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    6 nights
    4.5 star property
    9.4/10 - Exceptional (199 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • 1 stop
    £1,435
    £1,085
    per traveller
    found 3 hours ago
    The Talbott, Autograph Collection
  • 20 Jan - 26 Jan

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    6 nights
    4.5 star property
    9.4/10 - Exceptional (3,892 reviews)
    "Everything was perfect"
    Reviewed November 11, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • 1 stop
    £1,603
    £1,217
    per traveller
    found 3 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • 20 Jan - 26 Jan

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    8.4/10 - Very good (3,179 reviews)
    "Over charge for the room put deposit didn't received it back yet"
    Reviewed November 12, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • 1 stop
    £1,177
    £911
    per traveller
    found 3 hours ago
    Hotel Felix River North/Magnificent Mile

Where to stay in Darien

Find the best Darien areas for the activities you enjoy most. Learn more about Darien
Learn more about Darien

Lace

Lace is well liked for its restaurants and shopping. If you're hoping to see more of the larger area, Willowbrook Community Park and National Shrine of St. Therese are some interesting sights nearby to check out.

Discover the most popular places to visit in Darien

Darien Hotel Deals

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 travel package cost?

Customize your Darien package from an affordable £804. Choose from any combination of hotels, flights and rental cars to put together the escape you've been dreaming of. Be sure to add on one or two experiences!

If I'm not able to travel, can I cancel my Darien travel package?

We get that life sometimes gets in the way of your plans. If you've locked in a Darien travel package and need to change or cancel it, we can help. It's always worth looking up our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change your itinerary at no cost. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a fee.

How do I get a cheap travel package to Darien?

Simply by bundling. Hotels, rental cars and flights — combine whatever you need into a Darien travel package to save a ton of cash. Score even more deals when you include extras such as tours or experiences to your booking. But that's not the only impressive part. You have the flexibility to customize your trip your way. We offer more than 550 air carriers and 1,000,000 hotels around the world, so that everyone has an opportunity to travel and fulfil those holiday fantasies.

Does Expedia offer Book Now, Pay Later Darien holidays?

Your bank balance shouldn't prevent you from going on holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all types of budgets, so you can lock in that well-deserved holiday sooner.
  • Pay in instalments holidays: If you'd prefer to pay off your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you see an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Darien?

With interesting attractions like Twin Lakes Golf Course and Downers Grove Wine Shop in this area, look for a hotel located near them. Creekside Park is another sight that visitors flock to.

What are the top hotels in Darien?

Secure a room at Hyatt Regency Chicago. It's one of this area's most sought-after hotels. Another top option in Darien is The Godfrey Hotel Chicago.

How far in advance should I book my Darien holiday?

Be rewarded with the widest variety at the lowest prices by booking your holiday to Darien nice and early. Airlines generally sell flights around a year before departure, so start locking things in as soon as you can. Having said that, Expedia is committed to providing you with the best bargains around, so there's never a bad time to book your dream holiday!

What does an Expedia Darien travel package include?

Select from a combination of hotels, rental cars and flights. Once you've made your booking, you can add activities and experiences. Want to pick your airfare class? That's also possible. The choice is all yours when it comes to putting together your ideal Darien trip.

What should I know before booking a Darien travel package?

Bundling your bookings into a Darien travel package is the most convenient way to organise your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?

Can I choose my airline with a Darien Expedia travel package?

You can, and with over 550 airlines to pick from all over the world, it's all about choice. Have a look through the available options and see which airline best fits your budget and needs.

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