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Destin

Cheap flights from O'Hare Intl (ORD) to Destin (DSI)

ORD — DSI
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Destin

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Destin (DSI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Popular in

January

Cheapest in

August

Average price

$339
Provider with most accurate pricing for Chicago O'Hare Intl-Destin flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Destin flights.
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Highest demand for flights based on searches. 23% potential increase in price ($113 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Compare providers for flights from O'Hare Intl to Destin

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Destin in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Destin flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Destin flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Destin flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Destin flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Destin flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Destin

Have a flexible travel schedule? Discover the best time to fly to Destin from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Destin

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Destin?

Currently, April is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Destin (average of $137). Flying from Chicago O'Hare Intl Airport to Destin in December is currently the most expensive (average of $228). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to DSI?

Find hourly flight availability from O'Hare Intl to Destin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 27, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Destin is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 69% on airfare.

Reviews of airlines servicing Destin

Get insights into the airlines that provide service to Destin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Destin. Reviews last updated October 27, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Destin, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,997 reviews

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Destin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Destin from Chicago O'Hare Intl?

    Destin (DSI) is the airport you will fly into if you book a flight from Chicago O'Hare Intl to Destin. You should not have trouble finding flights to Destin from Chicago O'Hare Intl; the airport handles an average of 0 inbound flights from Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 1 airline has flights to the Destin airport from Chicago O'Hare Intl. It is only a 1.5 mi journey from Destin (DSI) to Destin’s city center.

  • What is the cheapest airline to fly from Chicago O'Hare Intl Airport to Destin round-trip?

    Flying on United Airlines is currently your cheapest option to Destin, with prices starting at $288. Users have found that United Airlines is 20% cheaper than the other options available to this destination.

  • Can I find deals for flights from O'Hare Intl to Destin that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Destin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Destin?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Destin.

  • Can I find deals for business class flights from O'Hare Intl to Destin?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Destin by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Destin?

    Currently, April is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Destin (average of $137). Flying from Chicago O'Hare Intl Airport to Destin in December is currently the most expensive (average of $228). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Destin?

Book flights to Destin if you plan to visit one of these locations
Miramar Beach
Santa Rosa Beach

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Alternative routes for O'Hare Intl to Destin

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Top airline flying from O'Hare Intl to Destin

Discover the top airline that operate flights from O'Hare Intl to Destin. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$288Average$442FlexibilityNo cancel feeOn-time69%

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