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Darien

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Darien Flights as Low as $58

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

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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 $58, 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 $58 right now, why wait?

Darien Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$58

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! (9,797 reviews)
Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...

Reviewed on Jan 20, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,553 reviews)
Did not have breakfast

Reviewed on Jan 19, 2026

Hilton 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 ...
9.2/10 Wonderful! (3,262 reviews)
Clean room, excellent staff

Reviewed on Jan 19, 2026

The Royal Sonesta Chicago Downtown
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 ...
8.6/10 Excellent! (4,933 reviews)
Love the coffee on 2nd floor- game changer! Clean, convenient, very affordable

Reviewed on Jan 20, 2026

River Hotel
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (3,570 reviews)
Beautiful hotel, I was disappointed by the lack of towel rack/hooks in the bathroom.

Reviewed on Jan 23, 2026

LondonHouse Chicago, Curio Collection by Hilton
Pendry Chicago

Pendry Chicago

4.5 out of 5
230 North Michigan Avenue Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,142 reviews)
N/A

Reviewed on Jan 12, 2026

Pendry Chicago
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 hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.4/10 Very Good! (5,587 reviews)
Great room. Great location. Everything was clean.

Reviewed on Jan 23, 2026

Embassy Suites by Hilton Chicago Downtown River North
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
Book a stay at this 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! (2,127 reviews)
Love this hotel 10/10

Reviewed on Jan 20, 2026

Holiday Inn Chicago Dwtn - The Mart by IHG
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.