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Destin

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

CHI — DSI
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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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 June 16, 2025.

Popular in

May

Cheapest in

January

Average price

$448
Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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, January is the cheapest month in which you can book a flight from Chicago to Destin (average of $240). Flying from Chicago to Destin in December is currently the most expensive (average of $424). 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 June 16, 2025.

It’s typically best to fly out from Chicago to Destin in the evening. Doing so could potentially save you 41% on the flight price compared to flying in the afternoon, which is usually more expensive.

Rainfall in Destin by month

Plan your trip to Destin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Destin ranges from 3.3 - 7.9 inches per month. July is typically the wettest month, when rainfall can reach 7.9 in. May is typically the driest time to visit Destin when rainfall is around 3.3 in.

Temperature in Destin by month

Plan your trip to Destin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Destin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 53.6 F).

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.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Destin (average of $240). Flying from Chicago to Destin in December is currently the most expensive (average of $424). 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 Chicago?

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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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$297Average$593FlexibilityNo cancel feeOn-time69%

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