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Darien

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Darien Flights as Low as $63

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

Spirit Airlines
Tue, Aug 5 - Wed, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $63 found 1 day ago
Spirit Airlines
Sat, Aug 2 - Tue, Aug 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 3 hours ago
$72
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Aug 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 5, priced at $72 found 3 hours ago
Spirit Airlines
Tue, Aug 12 - Tue, Aug 19
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$80 Roundtrip, found 8 hours ago
$80
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Tue, Aug 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 19, priced at $80 found 8 hours ago
Spirit Airlines
Sat, Aug 16 - Wed, Aug 20
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$82 Roundtrip, found 2 days ago
$82
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $82 found 2 days ago
Spirit Airlines
Sat, Sep 27 - Tue, Sep 30
LGA
LaGuardia
ORD
O'Hare Intl.
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Sep 27 from LaGuardia to O'Hare Intl., returning Tue, Sep 30, priced at $90 just found
JetBlue Airways
Thu, Oct 23 - Tue, Oct 28
BOS
Logan Intl.
ORD
O'Hare Intl.
$91 Roundtrip, found 2 days ago
$91
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Oct 23 from Logan Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $91 found 2 days ago
United
Thu, Oct 23 - Tue, Oct 28
BOS
Logan Intl.
ORD
O'Hare Intl.
$91 Roundtrip, found 2 days ago
$91
Roundtrip
found 2 days ago
Select United flight, departing Thu, Oct 23 from Logan Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $91 found 2 days ago
American Airlines
Thu, Oct 23 - Tue, Oct 28
BOS
Logan Intl.
ORD
O'Hare Intl.
$91 Roundtrip, found 2 days ago
$91
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Oct 23 from Logan Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $91 found 2 days ago
Delta
Sun, Sep 28 - Tue, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Sep 30, priced at $98 found 2 days ago
Frontier Airlines
Sun, Jul 27 - Tue, Jul 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jul 27 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $100 found 1 day ago
Frontier Airlines
Sat, Aug 16 - Mon, Aug 18
DEN
Denver Intl.
ORD
O'Hare Intl.
$125 Roundtrip, found 6 days ago
$125
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Denver Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $125 found 6 days ago
Delta
Wed, Aug 13 - Mon, Aug 18
BOS
Logan Intl.
MDW
Midway Intl.
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Aug 13 from Logan Intl. to Midway Intl., returning Mon, Aug 18, priced at $139 found 4 days ago
Frontier Airlines
Fri, Aug 1 - Sat, Aug 2
DEN
Denver Intl.
MDW
Midway Intl.
$156 Roundtrip, found 12 hours ago
$156
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Aug 1 from Denver Intl. to Midway Intl., returning Sat, Aug 2, priced at $156 found 12 hours ago
Frontier Airlines
Mon, Aug 4 - Mon, Aug 11
IAH
George Bush Intercontinental
MDW
Midway Intl.
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Aug 4 from George Bush Intercontinental to Midway Intl., returning Mon, Aug 11, priced at $176 found 1 day ago
Delta
Tue, Nov 4 - Tue, Nov 11
LGA
LaGuardia
MDW
Midway Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 4 from LaGuardia to Midway Intl., returning Tue, Nov 11, priced at $217 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Dec 23 - Tue, Dec 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$325 Roundtrip, found 5 days ago
$325
Roundtrip
found 5 days 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 $325 found 5 days 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 $63, 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 $63 right now, why wait?

Darien Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,936 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Get rates
Congress Plaza Hotel
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! (1,250 reviews)
"Good place to stay"

Reviewed on Jul 13, 2025

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Crowne Plaza Chicago West Loop by IHG
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! (4,416 reviews)
"We had a wonderful stay in Chicago."

Reviewed on Jul 11, 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! (3,338 reviews)
"This hotel and room were gorgeous. There was an iPad lighting system that my daughter loved. The terrace space was gorgeous and comfortable."

Reviewed on Jul 11, 2025

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citizenM Chicago Downtown
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! (1,856 reviews)
"Very clean and comfortable room."

Reviewed on Jul 12, 2025

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Hotel Felix River North/Magnificent Mile
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 ...
9.2/10 Wonderful! (2,699 reviews)
Excellent experience
"excellent stay. stay is great. Reception Angie was above and beyond. Bellman Arturo was great , very helpful, above and beyond. Great culture all around"

Reviewed on Jul 11, 2025

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The Royal Sonesta Chicago Downtown
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 3-star 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. ...
8.2/10 Very Good! (3,517 reviews)
"Great help and facility"

Reviewed on Jul 10, 2025

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Hilton Garden Inn Chicago Downtown/Magnificent Mile
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
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 ...
8.8/10 Excellent! (1,700 reviews)
"."

Reviewed on Jul 11, 2025

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Holiday Inn Chicago Dwtn - The Mart by IHG
See all 3,660 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.