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Darien

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Darien Flights as Low as $48

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

Frontier Airlines
Tue, Feb 25 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$48 Roundtrip, found 1 day ago
$48
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 25 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Mar 4, priced at $48 found 1 day ago
Frontier Airlines
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $63 found 1 day ago
Frontier Airlines
Tue, Feb 25 - Tue, Mar 4
DEN
Denver Intl.
MDW
Midway Intl.
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Feb 25 from Denver Intl. to Midway Intl., returning Tue, Mar 4, priced at $68 found 3 days ago
Spirit Airlines
Tue, Mar 25 - Tue, Apr 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Mar 25 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Apr 1, priced at $73 found 1 day ago
Frontier Airlines
Tue, Apr 1 - Tue, Apr 8
DEN
Denver Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 4 days ago
$80
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Apr 1 from Denver Intl. to O'Hare Intl., returning Tue, Apr 8, priced at $80 found 4 days ago
Frontier Airlines
Wed, Mar 26 - Wed, Apr 2
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Mar 26 from Raleigh - Durham Intl. to Midway Intl., returning Wed, Apr 2, priced at $119 found 3 days ago
Frontier Airlines
Tue, Apr 15 - Thu, Apr 24
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 18 hours ago
$119
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, Apr 15 from Raleigh - Durham Intl. to O'Hare Intl., returning Thu, Apr 24, priced at $119 found 18 hours ago
Frontier Airlines
Tue, Feb 11 - Wed, Feb 12
SLC
Salt Lake City Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 15 hours ago
$119
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, Feb 11 from Salt Lake City Intl. to O'Hare Intl., returning Wed, Feb 12, priced at $119 found 15 hours ago
American Airlines
Tue, Mar 4 - Tue, Mar 4
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 Tue, Mar 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 4, priced at $132 found 1 day ago
Delta
Wed, Mar 12 - Wed, Mar 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Mar 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Mar 12, priced at $134 found 1 day ago
United
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select United flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $137 found 1 day ago
JetBlue Airways
Mon, Feb 10 - Wed, Feb 19
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 15 hours ago
$193
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Mon, Feb 10 from Raleigh - Durham Intl. to O'Hare Intl., returning Wed, Feb 19, priced at $193 found 15 hours ago
Alaska Airlines
Wed, Jan 29 - Tue, Feb 4
SLC
Salt Lake City Intl.
ORD
O'Hare Intl.
$304 Roundtrip, found 2 days ago
$304
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Jan 29 from Salt Lake City Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $304 found 2 days ago
Air Canada
Sun, Feb 2 - Sun, Feb 9
AKL
Auckland Intl.
ORD
O'Hare Intl.
$930 Roundtrip, found 17 hours ago
$930
Roundtrip
found 17 hours ago
Select Air Canada flight, departing Sun, Feb 2 from Auckland Intl. to O'Hare Intl., returning Sun, Feb 9, priced at $930 found 17 hours ago
Qantas Airways
Mon, Feb 3 - Tue, Feb 11
AKL
Auckland Intl.
ORD
O'Hare Intl.
$1,162 Roundtrip, found 17 hours ago
$1,162
Roundtrip
found 17 hours ago
Select Qantas Airways flight, departing Mon, Feb 3 from Auckland Intl. to O'Hare Intl., returning Tue, Feb 11, priced at $1,162 found 17 hours ago
Delta
Mon, Apr 14 - Tue, Apr 15
AKL
Auckland Intl.
MDW
Midway Intl.
$1,915 Roundtrip, found 17 hours ago
$1,915
Roundtrip
found 17 hours ago
Select Delta flight, departing Mon, Apr 14 from Auckland Intl. to Midway Intl., returning Tue, Apr 15, priced at $1,915 found 17 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 February, 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 $48, 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 $48 right now, why wait?

Darien Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$48

Last Minute Hotel Deals in Darien

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $126 per night from Jan 12 to Jan 13
$126
includes taxes & fees
Jan 12 - Jan 13
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! (8,365 reviews)
"Loved the history of the hotel. accessible to everything"

Reviewed on Jan 8, 2025

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
The price is $115 per night from Jan 26 to Jan 27
$115
includes taxes & fees
Jan 26 - Jan 27
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. ...
8.2/10 Very Good! (3,454 reviews)
"Perfect"

Reviewed on Jan 9, 2025

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $113 per night from Jan 19 to Jan 20
$113
includes taxes & fees
Jan 19 - Jan 20
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! (3,687 reviews)
"The hotel is nice and located in a beautiful setting.."

Reviewed on Jan 9, 2025

River Hotel
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
The price is $173 per night from Jan 17 to Jan 18
$173
includes taxes & fees
Jan 17 - Jan 18
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,603 reviews)
Local events may impact your stay.
"We were offered a discounted upgrade upon check in. It was my birthday and we were excited to accept. The riom was spacious with an amazing view. Breakfast was delicious. My only complaint wasn't really the hotels fault but a little communication would have been helpful. We traveled out to the suburbs ..."

Reviewed on Jan 7, 2025

Hilton Chicago
Pendry Chicago
Pendry Chicago
4.5 out of 5
230 North Michigan Avenue, Chicago, IL
The price is $229 per night from Jan 26 to Jan 27
$229
includes taxes & fees
Jan 26 - Jan 27
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
9.2/10 Wonderful! (989 reviews)
"Great property, we loved the location dinning options and the room itself. We felt right at home. The only thing I didn’t care and I thought was a little much was $69 a night to park/valet my car with them! I understand the convenience of it but when I can pay for 2 nights across the street for one ..."

Reviewed on Jan 7, 2025

Pendry Chicago
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is $187 per night from Jan 12 to Jan 13
$187
includes taxes & fees
Jan 12 - Jan 13
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,413 reviews)
"Best experience ever"

Reviewed on Jan 9, 2025

L7 Chicago by LOTTE
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
The price is $169 per night from Jan 17 to Jan 18
$169
includes taxes & fees
Jan 17 - Jan 18
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,570 reviews)
"Would stay again!"

Reviewed on Jan 10, 2025

Palmer House a Hilton Hotel
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $118 per night from Jan 13 to Jan 14
$118
includes taxes & fees
Jan 13 - Jan 14
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! (1,410 reviews)
"Hotel Felix welcomes dogs and pet friendly. The dog park is walkable with a certain distance"

Reviewed on Jan 8, 2025

Hotel Felix River North/Magnificent Mile
See all 3,421 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.