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Darien

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Darien Flights as Low as $111

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

Frontier Airlines
Tue, Aug 11 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 11 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $111 found 1 day ago
Frontier Airlines
Wed, Jul 22 - Wed, Jul 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$131 Roundtrip, found 10 hours ago
$131
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Wed, Jul 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jul 22, priced at $131 found 10 hours ago
Frontier Airlines
Sat, Jul 4 - Tue, Jul 7
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$140 Roundtrip, found 15 hours ago
$140
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jul 7, priced at $140 found 15 hours ago
Frontier Airlines
Wed, Sep 2 - Wed, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 14 hours ago
$148
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $148 found 14 hours ago
Frontier Airlines
Tue, Aug 4 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$166 Roundtrip, found 17 hours ago
$166
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Aug 15, priced at $166 found 17 hours ago
American Airlines
Wed, Sep 23 - Wed, Sep 30
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$171 Roundtrip, found 2 days ago
$171
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Sep 23 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Sep 30, priced at $171 found 2 days ago
United
Wed, Sep 23 - Wed, Sep 30
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$171 Roundtrip, found 2 days ago
$171
Roundtrip
found 2 days ago
Select United flight, departing Wed, Sep 23 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Sep 30, priced at $171 found 2 days ago
Delta
Tue, Aug 11 - Sat, Aug 15
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$191 Roundtrip, found 12 hours ago
$191
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Aug 11 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Aug 15, priced at $191 found 12 hours ago
Frontier Airlines
Wed, Aug 5 - Tue, Aug 18
IAH
George Bush Intercontinental
MDW
Midway Intl.
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 5 from George Bush Intercontinental to Midway Intl., returning Tue, Aug 18, priced at $215 found 1 day ago
Delta
Thu, Nov 5 - Mon, Nov 9
HOU
William P. Hobby
ORD
O'Hare Intl.
$245 Roundtrip, found 2 days ago
$245
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 5 from William P. Hobby to O'Hare Intl., returning Mon, Nov 9, priced at $245 found 2 days ago
Delta
Sat, Jul 4 - Wed, Jul 8
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$282 Roundtrip, found 22 hours ago
$282
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Jul 4 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, Jul 8, priced at $282 found 22 hours ago
Delta
Sat, Aug 8 - Tue, Aug 11
DAL
Love Field
MDW
Midway Intl.
$285 Roundtrip, found 3 days ago
$285
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Aug 8 from Love Field to Midway Intl., returning Tue, Aug 11, priced at $285 found 3 days ago
Contour Airlines
Tue, Sep 1 - Wed, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$289 Roundtrip, found 15 hours ago
$289
Roundtrip
found 15 hours ago
Select Contour Airlines flight, departing Tue, Sep 1 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $289 found 15 hours ago
Delta
Sat, Sep 26 - Tue, Sep 29
DAL
Love Field
ORD
O'Hare Intl.
$291 Roundtrip, found 3 hours ago
$291
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Sep 26 from Love Field to O'Hare Intl., returning Tue, Sep 29, priced at $291 found 3 hours ago
JetBlue Airways
Wed, Aug 12 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Aug 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $347 found 1 day ago
Delta
Fri, Jul 24 - Mon, Jul 27
HOU
William P. Hobby
MDW
Midway Intl.
$639 Roundtrip, found 15 hours ago
$639
Roundtrip
found 15 hours ago
Select Delta flight, departing Fri, Jul 24 from William P. Hobby to Midway Intl., returning Mon, Jul 27, priced at $639 found 15 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 August, 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 $111, 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 $111 right now, why wait?

Darien Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$110

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! (10,139 reviews)
"Very cool old hotel in a great location. Well-restored and comfortable. Bell captains were very helpful with suggestions for local attractions and cabs."

Reviewed on Jul 2, 2026

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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
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! (2,337 reviews)
"I have severe mobility issues, but was taken by wheelchair directly from United gate to Hilton reception desk. Restaurants were close to reception and elevators, so accessible with stroller."

Reviewed on Jul 2, 2026

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Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,759 reviews)
"old fashion"

Reviewed on Jul 3, 2026

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Hyatt Regency O'Hare Chicago
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! (5,269 reviews)
"This is a beautiful hotel that is certainly photo worthy and should be on the city tour. The staff was super friendly and helpful. What I liked mostly about this hotel is how it was located to most of my tours and was right across the street from the riverwalk and provided a great view. There was ..."

Reviewed on Jul 3, 2026

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River Hotel
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 ...
7.6/10 Good! (2,643 reviews)
"Room had trash under the beds. The property has no filtered water except in a vending machine. Very good ac unit, free wifi, great views. Blue line train to and from airport and red line to and from wrigley field was awesome and cheap and right next to the hotel."

Reviewed on Jul 2, 2026

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Travelodge by Wyndham Downtown Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,509 reviews)
"The lobby looks great and impressive."

Reviewed on Jun 30, 2026

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Palmer House a Hilton Hotel
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. ...
7.8/10 Good! (3,150 reviews)
"Great location. Rooms were clean. Offsite parking for 49$. Rooms are really quite small. Very very slow and busy elevators. Phone didn’t work to call front desk. We kept being told someone would bring up a mini fridge to our room for our medications however it never got brought up and eventually ..."

Reviewed on Jul 2, 2026

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Freehand Chicago
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
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The Royal Sonesta Chicago Downtown
See all 3,807 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.