Darien Vacations from $522
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Talbott, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $522 per person
$522
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (128 reviews)
A hidden gem in the heart of the Gold Coast! Wonderful staff! Shout out to Steve! He made us feel right at home! Coffee machines in the room were amazing, the coffee was delicious! Thank you to all the staff for all that they do! Til next time!
Reviewed on Jul 5, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,524, price is now $1,602 per person
$1,602
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!
Reviewed on Jul 6, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $822, price is now $552 per person
$552
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Excellent spot, in the perfect location. Parking at the property is pretty expensive, but there are cheaper parking garages close by.
Reviewed on Jul 6, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,641, price is now $1,104 per person
$1,104
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location.
The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.
Reviewed on Jul 6, 2026
Stay near popular Darien attractions
What to do in Darien
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Darien Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Jul 8 to Jul 9
$215 total
Jul 8 - Jul 9
Total with taxes and fees
8/10 Very Good! (10,194 reviews)
"Bartender, Chris was very nice!"
Reviewed on Jul 6, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$169 nightly
The price is $193 total per night from Jul 8 to Jul 9
$193 total
Jul 8 - Jul 9
Total with taxes and fees
8.8/10 Excellent! (2,791 reviews)
"Everything"
Reviewed on Jul 6, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $269 total per night from Aug 7 to Aug 8
$269 total
Aug 7 - Aug 8
Total with taxes and fees
8.4/10 Very Good! (2,328 reviews)
"Very convenient to get up & walk to your flight. Good soundproofing."
Reviewed on Jul 7, 2026
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 |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Robert W Roloson Houses
- Rookery
- Humboldt Park
- Fourth Presbyterian Church
- Promenade Bolingbrook
- 900 North Michigan Shops
- Richard J. Daley Center
- Chicago Museum Campus Vacations
- Downers Grove Vacations
- Palisades Vacations
- Auditorium Building and Theatre
- Magnificent Mile Vacations
- Burr Ridge Vacations
- Rocket Ice Arena
- Canalport Riverwalk Park
- Willowbrook Vacations
- Film Row Cinema
- Chicago City Hall
- Chicago Vacations
- Willis Tower
- Chicago Place Mall
- Wheaton College
- Lincoln Park Zoo
- Michigan Avenue
- Jane Addams' Hull-House Museum
- Fisher Building
- Raging Waves Waterpark
- Anna and Frederick Douglass Park
- Marina City
- Unity Temple
- Tribune Tower
- Veterans Memorial Park
- Chase Tower
- Wicker Park Vacations
- Graue Mill and Museum
- Merchandise Mart
- Skydeck Ledge
- Willowbrook Community Park
- Chinatown Vacations
- West Loop Vacations
- American Police Center & Museum
- Monique Meloche Gallery
- Westmont Vacations
- St. Basil Greek Orthodox Church
- Ty Warner Park
- Grace Abbott Homes Vacations
- 333 West Wacker Drive
- Roosevelt University
- Wrigley Building
- Monadnock Building
- Marshall Field Building
- Our Lady of Sorrows Basilica
- Depaul University-Loop Campus
- Gen. John Logan Memorial
- Maxwell Street Market
- Civic Opera House
- Centennial Beach
- Shops at North Bridge
- St. John Cantius Church
- Illinois Centennial Memorial Column
- South Loop Vacations
- Cadillac Palace Theatre
- Bridgeport Art Center
- Ping Tom Memorial Park
- Flat Iron Building
- Holy Name Cathedral
- Mary Bartelme Park
- Sr Crown Hall
- Gorilla Tango Theatre
- South Commons Vacations
- The East Bank Club
- 311 S Wacker Dr
- Goodman Theater
- Morton Arboretum
- Robie House
- Zhou B Art Center
- Mayslake Peabody Mansion
- Chicago Children's Museum
- Picasso Statue
- Ida B Wells House
- Montrose Beach
- Wrigley Field
- Seatgeek Stadium
- Navy Pier
- Burnham Park
- Carbide and Carbon Building
- Cantigny Park
- Cibc Theatre
- Art Institute of Chicago
- The Salt Shed
- Packer Schopf Gallery
- Legoland® Discovery Center
- University of Illinois Chicago
- Creekside Park
- St Nicholas Ukrainian Catholic Cathedral
- Cooking & Hospitality Institute of Chicago
- Garfield Park
- Mccormick Tribune Center
- Driehaus Museum
- Holy Trinity Russian Orthodox Cathedral
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
