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Darien

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Darien Flights as Low as $56

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

Frontier Airlines
Tue, May 12 - Wed, May 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$56 Roundtrip, found 14 hours ago
$56
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Wed, May 13, priced at $56 found 14 hours ago
Frontier Airlines
Sat, Apr 25 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$68 Roundtrip, found 2 hours ago
$68
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Apr 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, May 2, priced at $68 found 2 hours ago
Spirit Airlines
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 1 hour ago
$73
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $73 found 1 hour ago
Frontier Airlines
Wed, Apr 22 - Thu, Apr 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 5 days ago
$80
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Apr 30, priced at $80 found 5 days ago
Spirit Airlines
Sat, Apr 25 - Tue, Apr 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Apr 25 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 28, priced at $93 found 1 day ago
Frontier Airlines
Tue, May 5 - Sat, May 16
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$104 Roundtrip, found 4 days ago
$104
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, May 16, priced at $104 found 4 days ago
Frontier Airlines
Thu, Apr 30 - Tue, May 5
IAH
George Bush Intercontinental
MDW
Midway Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 30 from George Bush Intercontinental to Midway Intl., returning Tue, May 5, priced at $142 found 1 day ago
United
Tue, May 12 - Tue, May 19
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$172 Roundtrip, just found
$172
Roundtrip
just found
Select United flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 19, priced at $172 just found
American Airlines
Tue, May 12 - Tue, May 19
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$172 Roundtrip, just found
$172
Roundtrip
just found
Select American Airlines flight, departing Tue, May 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, May 19, priced at $172 just found
Contour Airlines
Mon, May 18 - Thu, May 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 17 hours ago
$193
Roundtrip
found 17 hours ago
Select Contour Airlines flight, departing Mon, May 18 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, May 21, priced at $193 found 17 hours ago
Delta
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 3 hours ago
$195
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $195 found 3 hours ago
Frontier Airlines
Fri, Apr 24 - Sat, May 2
LAX
Los Angeles Intl.
MDW
Midway Intl.
$209 Roundtrip, found 8 hours ago
$209
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Apr 24 from Los Angeles Intl. to Midway Intl., returning Sat, May 2, priced at $209 found 8 hours ago
Delta
Sat, May 9 - Tue, May 12
DAL
Love Field
MDW
Midway Intl.
$222 Roundtrip, found 22 hours ago
$222
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, May 9 from Love Field to Midway Intl., returning Tue, May 12, priced at $222 found 22 hours ago
Delta
Tue, May 12 - Sat, May 16
DAL
Love Field
ORD
O'Hare Intl.
$241 Roundtrip, just found
$241
Roundtrip
just found
Select Delta flight, departing Tue, May 12 from Love Field to O'Hare Intl., returning Sat, May 16, priced at $241 just found
Alaska Airlines
Wed, May 6 - Thu, May 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$345 Roundtrip, found 13 hours ago
$345
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Wed, May 6 from Los Angeles Intl. to O'Hare Intl., returning Thu, May 7, priced at $345 found 13 hours ago
JetBlue Airways
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$375 Roundtrip, found 19 hours ago
$375
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $375 found 19 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 May, 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 16 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 $56, 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 $56 right now, why wait?

Darien Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$56

Last Minute Hotel Deals in Darien

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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,080 reviews)
Parking was terrible and extremely expensive

Reviewed on Apr 10, 2026

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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
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,833 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on Apr 9, 2026

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Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,263 reviews)
I keep coming back to this hotel because of the location, but honestly it is a disappointment every time. The rooms are dated, the carpets are old and worn, and the elevators are slow. The door to my room was broken, so every time I wanted to leave for food or go to gym, I had to go downstairs, alert ...

Reviewed on Apr 9, 2026

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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
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,615 reviews)
Everything was just right. Clean room, quite hallways so I was able to sleep well and the location was conveniently located. I did not try the room service or other amenities that were available on site, but will definitely do so and add an updated review after my next trip.

Reviewed on Apr 11, 2026

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Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,074 reviews)
Good location, friendly staff

Reviewed on Apr 10, 2026

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River Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,725 reviews)
Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by.

Reviewed on Apr 11, 2026

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Hilton Chicago
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (2,859 reviews)
I asked to fix my outlet on my room to fix it to give me extension cord but seems they don't have time to do it .

Reviewed on Apr 9, 2026

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Freehand Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8.6/10 Excellent! (4,431 reviews)
Room was clean

Reviewed on Apr 10, 2026

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Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 3,972 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.