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Darien

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Darien Flights as Low as $80

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Jul 8 - Tue, Jul 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $80 found 1 day ago
Spirit Airlines
Sat, Sep 6 - Tue, Sep 9
MCO
Orlando Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 9 hours ago
$100
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Sat, Sep 6 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $100 found 9 hours ago
Frontier Airlines
Tue, Aug 5 - Wed, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Aug 6, priced at $108 found 1 day ago
United
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select United flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $132 found 2 hours ago
Delta
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $132 found 2 hours ago
American Airlines
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $132 found 1 day ago
Frontier Airlines
Fri, Jul 18 - Sat, Jul 26
MCO
Orlando Intl.
MDW
Midway Intl.
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Jul 18 from Orlando Intl. to Midway Intl., returning Sat, Jul 26, priced at $152 found 5 days ago
United
Mon, Jun 30 - Wed, Jul 2
IAD
Washington Dulles Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 14 hours ago
$179
Roundtrip
found 14 hours ago
Select United flight, departing Mon, Jun 30 from Washington Dulles Intl. to O'Hare Intl., returning Wed, Jul 2, priced at $179 found 14 hours ago
Bargain Flight
Tue, Jul 22 - Wed, Jul 23
JAX
Jacksonville Intl.
ORD
O'Hare Intl.
$208 Roundtrip, found 6 hours ago
$208
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Tue, Jul 22 from Jacksonville Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $208 found 6 hours ago
Frontier Airlines
Wed, Jun 25 - Mon, Jun 30
ONT
Los Angeles - Ontario Intl.
MDW
Midway Intl.
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jun 25 from Los Angeles - Ontario Intl. to Midway Intl., returning Mon, Jun 30, priced at $214 found 2 days ago
Frontier Airlines
Tue, Jun 24 - Tue, Jul 1
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$246 Roundtrip, found 6 hours ago
$246
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Jun 24 from Washington Dulles Intl. to Midway Intl., returning Tue, Jul 1, priced at $246 found 6 hours ago
JetBlue Airways
Sat, Sep 6 - Tue, Sep 9
MCO
Orlando Intl.
ORD
O'Hare Intl.
$248 Roundtrip, found 9 hours ago
$248
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $248 found 9 hours ago
Frontier Airlines
Fri, Jun 27 - Fri, Jul 4
JAX
Jacksonville Intl.
MDW
Midway Intl.
$274 Roundtrip, found 6 hours ago
$274
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Jun 27 from Jacksonville Intl. to Midway Intl., returning Fri, Jul 4, priced at $274 found 6 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Dec 23 - Tue, Dec 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$296 Roundtrip, found 3 hours ago
$296
Roundtrip
found 3 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Dec 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 30, priced at $296 found 3 hours ago
Frontier Airlines
Mon, Aug 11 - Tue, Aug 19
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$317 Roundtrip, found 3 hours ago
$317
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Aug 11 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $317 found 3 hours ago
Alaska Airlines
Tue, Aug 12 - Wed, Aug 20
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$324 Roundtrip, found 3 hours ago
$324
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Tue, Aug 12 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $324 found 3 hours ago

Cheap Flights to Darien

Fall in love at first flight with your vacation to Darien by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Darien on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Darien, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Darien

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Darien with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Darien?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Darien are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Darien?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Darien.

What airport is best to fly into Darien?

When you’re planning your trip to Darien, convenience is the name of the game. Luckily, Darien Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Darien must-do list.

How much are flights to Darien?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Darien on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $80, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Darien?

The trick to saving a stack of cash on your flight to Darien? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $80 right now, why wait?

Darien Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$80

Last Minute Hotel Deals in Darien

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
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,244 reviews)
"Great stay, amazing late night staff assisted with late check in. Clean, comfortable rooms. Good hot breakfast. Broken TV in room they couldn’t fix was only downside."

Reviewed on Jun 20, 2025

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Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,200 reviews)
"The entire stay was an experience like no other that neither me nor my partner expected. The minimal personnel paired with the self service check in was eerie at first, seeming too good to be true, but after talking to the wonderful staff I came to understand the love put into this hotel and the ..."

Reviewed on Jun 20, 2025

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citizenM Chicago Downtown
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,846 reviews)
"Good"

Reviewed on Jun 19, 2025

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Congress Plaza Hotel
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8/10 Very Good! (2,056 reviews)
"Good choice!"

Reviewed on Jun 19, 2025

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Hilton Chicago O'Hare Airport
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,769 reviews)
"Compared to the stay I had at a different place right before this, this was great. It was quiet and straight forward. The staff was so nice and welcoming. I had everything I needed and it was great. Would definitely stay again!"

Reviewed on Jun 18, 2025

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Hotel Felix River North/Magnificent Mile
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7/10 Good! (2,203 reviews)
Nice and centrally located
"It's in a great part of the city. very close to transit lines and nearby restaurants. Hotel itself was "nice". It's a type of room that you can get a good night's rest before you go out and sightsee. Not much of a place where you'd want to just hangout. Desk staff not the most congenial, but my interactions ..."

Reviewed on Jun 18, 2025

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Travelodge by Wyndham Downtown Chicago
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,145 reviews)
"Incredibly friendly and helpful staff. Told me best local stores to buy food/drinks, as well as a bunch of great local restaurants. Even lent me a bottle opener when I needed one. Everyone was so nice and the hotel was clean and had everything I could want, right near the fun part of town."

Reviewed on Jun 18, 2025

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Crowne Plaza Chicago West Loop by IHG
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (4,258 reviews)
"Great location."

Reviewed on Jun 18, 2025

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River Hotel
See all 3,621 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.