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Darien

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Darien Flights as Low as $88

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

Frontier Airlines
Sat, Jul 12 - Tue, Jul 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $88 found 3 days ago
Frontier Airlines
Tue, Jun 24 - Wed, Jun 25
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$108 Roundtrip, found 4 days ago
$108
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jun 24 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Jun 25, priced at $108 found 4 days ago
Spirit Airlines
Mon, Sep 22 - Fri, Sep 26
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 4 days ago
$128
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Mon, Sep 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Fri, Sep 26, priced at $128 found 4 days ago
Bargain Flight
Sat, May 17 - Mon, May 19
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, May 17 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Mon, May 19, priced at $163 found 2 days ago
Frontier Airlines
Fri, Jun 6 - Mon, Jun 9
MCI
Kansas City Intl.
ORD
O'Hare Intl.
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jun 6 from Kansas City Intl. to O'Hare Intl., returning Mon, Jun 9, priced at $173 found 1 day ago
American Airlines
Wed, Jul 2 - Sat, Jul 12
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 22 hours ago
$177
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Wed, Jul 2 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jul 12, priced at $177 found 22 hours ago
Delta
Tue, Jul 8 - Tue, Jul 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 8, priced at $191 found 1 day ago
Bargain Flight
Wed, Aug 27 - Fri, Aug 29
RIC
Richmond Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 6 days ago
$192
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Wed, Aug 27 from Richmond Intl. to O'Hare Intl., returning Fri, Aug 29, priced at $192 found 6 days ago
Delta
Wed, Jul 2 - Sat, Jul 12
DAL
Love Field
ORD
O'Hare Intl.
$197 Roundtrip, found 22 hours ago
$197
Roundtrip
found 22 hours ago
Select Delta flight, departing Wed, Jul 2 from Love Field to O'Hare Intl., returning Sat, Jul 12, priced at $197 found 22 hours ago
Delta
Sat, Jul 19 - Tue, Jul 22
RIC
Richmond Intl.
MDW
Midway Intl.
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jul 19 from Richmond Intl. to Midway Intl., returning Tue, Jul 22, priced at $201 found 5 days ago
Frontier Airlines
Fri, May 23 - Wed, May 28
MCI
Kansas City Intl.
MDW
Midway Intl.
$204 Roundtrip, found 20 hours ago
$204
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Fri, May 23 from Kansas City Intl. to Midway Intl., returning Wed, May 28, priced at $204 found 20 hours ago
Contour Airlines
Thu, Jul 10 - Sun, Jul 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Thu, Jul 10 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $209 found 3 days ago
Frontier Airlines
Mon, May 12 - Thu, May 15
CVG
Cincinnati - Northern Kentucky Intl.
MDW
Midway Intl.
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 12 from Cincinnati - Northern Kentucky Intl. to Midway Intl., returning Thu, May 15, priced at $213 found 1 day ago
Delta
Tue, Jun 24 - Wed, Jun 25
DAL
Love Field
MDW
Midway Intl.
$220 Roundtrip, found 4 days ago
$220
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jun 24 from Love Field to Midway Intl., returning Wed, Jun 25, priced at $220 found 4 days ago
United
Thu, May 8 - Wed, Jun 11
MLM
General Francisco Mujica Intl.
ORD
O'Hare Intl.
$338 Roundtrip, found 6 days ago
$338
Roundtrip
found 6 days ago
Select United flight, departing Thu, May 8 from General Francisco Mujica Intl. to O'Hare Intl., returning Wed, Jun 11, priced at $338 found 6 days ago
Frontier Airlines
Sat, Jul 12 - Tue, Aug 12
MLM
General Francisco Mujica Intl.
MDW
Midway Intl.
$367 Roundtrip, found 18 hours ago
$367
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sat, Jul 12 from General Francisco Mujica Intl. to Midway Intl., returning Tue, Aug 12, priced at $367 found 18 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 14 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 $88, 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 $88 right now, why wait?

Darien Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$79

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 $157 per night from May 27 to May 28
$157
includes taxes & fees
May 27 - May 28
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! (8,749 reviews)
"Great!"

Reviewed on May 4, 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 $189 per night from May 12 to May 13
$189
includes taxes & fees
May 12 - May 13
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! (3,982 reviews)
"Excellent hotel"

Reviewed on May 2, 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 $164 per night from May 26 to May 27
$164
includes taxes & fees
May 26 - May 27
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! (4,115 reviews)
"Perfect location to enjoy the Chicago river walk at any time of the day. Walkable to all famous places and to great restaurants. Chose the option to include breakfast which was excellent. Chose the valet parking which provided us the freedom to visit Chicago outskirts during the stay. Will stay here ..."

Reviewed on May 5, 2025

River Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG
Holiday Inn Chicago Dwtn - The Mart by IHG
3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is $215 per night from May 27 to May 28
$215
includes taxes & fees
May 27 - May 28
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,556 reviews)
"Great"

Reviewed on May 2, 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $131 per night from May 26 to May 27
$131
includes taxes & fees
May 26 - May 27
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! (3,003 reviews)
"It’s a beautiful property with excellent staff."

Reviewed on May 3, 2025

citizenM Chicago Downtown
The Allegro Royal Sonesta Hotel Chicago Loop
The Allegro Royal Sonesta Hotel Chicago Loop
4 out of 5
171 W Randolph St, Chicago, IL
The price is $232 per night from May 26 to May 27
$232
includes taxes & fees
May 26 - May 27
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
8.8/10 Excellent! (1,686 reviews)
"Overall this property is lovely. The public areas are plentiful and feel luxuriously hip and comfortable. Though compact, the gym was great, lots of equipment in a very shareable space. Everything was clean and comfortable in the room. My room was at the end of the building above the metro track, ..."

Reviewed on May 3, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
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 $166 per night from May 6 to May 7
$166
includes taxes & fees
May 6 - May 7
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! (1,634 reviews)
"Staff was helpful. Great location with plenty of dining options in the area"

Reviewed on May 3, 2025

Hotel Felix River North/Magnificent Mile
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
The price is $133 per night from May 27 to May 28
$133
includes taxes & fees
May 27 - May 28
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! (1,021 reviews)
"Satisfied with the overall stay."

Reviewed on May 4, 2025

Crowne Plaza Chicago West Loop by IHG
See all 3,466 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.