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Darien

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Darien Flights as Low as $83

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

Spirit Airlines
Sat, Aug 23 - Wed, Aug 27
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 2 days ago
$83
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Aug 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 27, priced at $83 found 2 days ago
Frontier Airlines
Thu, Sep 4 - Mon, Sep 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Sep 15, priced at $90 found 1 day ago
American Airlines
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$93 Roundtrip, found 6 hours ago
$93
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $93 found 6 hours ago
Frontier Airlines
Sun, Sep 28 - Wed, Oct 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Oct 1, priced at $100 found 1 day ago
Frontier Airlines
Mon, Sep 29 - Mon, Oct 6
DEN
Denver Intl.
ORD
O'Hare Intl.
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Denver Intl. to O'Hare Intl., returning Mon, Oct 6, priced at $111 found 2 days ago
United
Sat, Aug 30 - Mon, Sep 1
SAN
San Diego Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 30 from San Diego Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $112 found 1 day ago
Frontier Airlines
Mon, Nov 3 - Thu, Nov 6
DEN
Denver Intl.
MDW
Midway Intl.
$114 Roundtrip, found 13 hours ago
$114
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Denver Intl. to Midway Intl., returning Thu, Nov 6, priced at $114 found 13 hours ago
United
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$115 Roundtrip, found 6 hours ago
$115
Roundtrip
found 6 hours ago
Select United flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $115 found 6 hours ago
Delta
Sun, Sep 28 - Tue, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 2 hours ago
$117
Roundtrip
found 2 hours ago
Select Delta flight, departing Sun, Sep 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 30, priced at $117 found 2 hours ago
Frontier Airlines
Mon, Oct 27 - Thu, Oct 30
LAS
Harry Reid Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Oct 27 from Harry Reid Intl. to O'Hare Intl., returning Thu, Oct 30, priced at $120 found 1 day ago
Hawaiian Airlines
Tue, Oct 7 - Sat, Oct 11
SAN
San Diego Intl.
ORD
O'Hare Intl.
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Tue, Oct 7 from San Diego Intl. to O'Hare Intl., returning Sat, Oct 11, priced at $139 found 2 days ago
American Airlines
Thu, Sep 11 - Sun, Sep 14
SAT
San Antonio Intl.
ORD
O'Hare Intl.
$194 Roundtrip, found 1 day ago
$194
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 11 from San Antonio Intl. to O'Hare Intl., returning Sun, Sep 14, priced at $194 found 1 day ago
Delta
Sat, Sep 13 - Sat, Sep 13
SAT
San Antonio Intl.
MDW
Midway Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 13 from San Antonio Intl. to Midway Intl., returning Sat, Sep 13, priced at $217 found 1 day ago
Delta
Sat, Aug 30 - Tue, Sep 2
LAS
Harry Reid Intl.
MDW
Midway Intl.
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 30 from Harry Reid Intl. to Midway Intl., returning Tue, Sep 2, priced at $240 found 2 days ago
American Airlines
Fri, Sep 5 - Mon, Sep 8
CLD
McClellan-Palomar
ORD
O'Hare Intl.
$257 Roundtrip, found 17 hours ago
$257
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Fri, Sep 5 from McClellan-Palomar to O'Hare Intl., returning Mon, Sep 8, priced at $257 found 17 hours ago
Frontier Airlines
Fri, Aug 29 - Sun, Aug 31
SAN
San Diego Intl.
MDW
Midway Intl.
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 29 from San Diego Intl. to Midway Intl., returning Sun, Aug 31, priced at $268 found 1 day 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 $83, 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 $83 right now, why wait?

Darien Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$83

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! (8,984 reviews)
"I love it"

Reviewed on Aug 5, 2025

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Congress Plaza Hotel
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 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! (1,832 reviews)
"Central location to everything"

Reviewed on Aug 6, 2025

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Palmer House a Hilton 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! (1,350 reviews)
"Wonderful property but at this price i expect parking or at least a discount option"

Reviewed on Aug 5, 2025

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Crowne Plaza Chicago West Loop by IHG
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. ...
8.4/10 Very Good! (3,627 reviews)
"It was conveniently located downtown and within walking distance of the river, shopping, Millennium Park, and dining. Close to Subway to Wrigley Field and O’Hare."

Reviewed on Aug 6, 2025

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Hilton Garden Inn Chicago Downtown/Magnificent Mile
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! (4,618 reviews)
Amazing hotel stay!
"The hotel was beautiful & spacious. All of the staff were courteous & friendly. They offer 2 free complimentary drinks a day during happy hour & the complimentary breakfast has plenty of options; pancakes, eggs, sausage, hash browns, toast/bagel/muffin station, oatmeal station, cereal bar & a build ..."

Reviewed on Aug 4, 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! (3,522 reviews)
"stayed here for the lollapalooza weekend and it was convenient to walk to the festival! the lobby floor was nice as there are lots of seating and a terrance lounge as well! lots of food places around the hotel!"

Reviewed on Aug 5, 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! (1,989 reviews)
Recommended
"Staff was very friendly and helpful. Rooms are quite small, but well kept. Few parking options nearby. Great location. Overall, a solid place to stay at a good price point."

Reviewed on Aug 5, 2025

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Hotel Felix River North/Magnificent Mile
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
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! (1,925 reviews)
"We chose this hotel for its proximity to Grant Park for Lollapoloza, it was great, clean and quiet! We enjoyed our stay."

Reviewed on Aug 5, 2025

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The Allegro Royal Sonesta Hotel Chicago Loop
See all 3,758 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.