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Destin

Cheap flights from Chicago (CHI) to Destin (DSI)

CHI — DSI
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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1. Tell us where you want to go

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Cheap flight deals from Chicago to Destin

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

October

Cheapest in

January

Average price

$690
Provider with most accurate pricing for Chicago (CHI)-Destin flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Destin flights.
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Compare providers for flights from Chicago 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 Chicago to Destin in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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-Destin flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Destin flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Destin flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Destin flights, Cheapflights users trust FlightHub the most. FlightHub 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-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 Chicago to Destin

Have a flexible travel schedule? Discover the best time to fly to Destin from Chicago 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 to Destin

What is the cheapest month to book a flight from Chicago to Destin?

Currently, July is the cheapest month in which you can book a flight from Chicago to Destin (average of $81). Flying from Chicago to Destin in August is currently the most expensive (average of $197). 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 CHI to DSI?

Find hourly flight availability from Chicago 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 20, 2025.

It’s typically best to fly out from Chicago to Destin in the evening. Doing so could potentially save you 57% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 20, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and Allegiant Air from Chicago to Destin by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,977 reviews

Boarding

8.2

Food

7.3

Overall

7.9

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
7,977 reviews
Delta
7.9
Good
7,977 reviews

Boarding

8.2

Food

7.3

Overall

7.9

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
8,988 reviews
Delta
7.9
Good
7,977 reviews

Boarding

8.2

Food

7.3

Overall

7.9

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Allegiant Air
7.2
Good
694 reviews
Delta
7.9
Good
7,977 reviews

Boarding

8.2

Food

7.3

Overall

7.9

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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?

    Located just 1.5 mi from the city center, Destin is the airport most travelers will use when flying to Destin from Chicago. Booking flights from Chicago to Destin (DSI) should be relatively easy as there are 0 daily inbound flights from Chicago from 1 airline.

  • What is the cheapest airline to fly from Chicago to Destin round-trip?

    According to our current data, United Airlines ($288), offers the cheapest pricing from Chicago to Destin. United Airlines is priced at 27% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Chicago to Destin that include hotel bookings?

    Yes. In addition to deals on Chicago to Destin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Destin?

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

  • Can I find deals for business class flights from Chicago to Destin?

    Yes. Cheapflights offers flight deals from Chicago 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 to Destin?

    Currently, July is the cheapest month in which you can book a flight from Chicago to Destin (average of $81). Flying from Chicago to Destin in August is currently the most expensive (average of $197). 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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Top airline flying from Chicago to Destin

Discover the top airline that operate flights from Chicago 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$288Average$442FlexibilityNo cancel feeOn-time69%

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