CHI - DSI

Find cheap flights from Chicago to Destin

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Destin

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Destin, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Destin, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Chicago to Destin (CHI-DSI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Destin that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Destin

Multiple Airlines Logo
CHI-DSI
795 mimulti-stop
Multiple Airlines Logo
DSI-CHI
795 mimulti-stop
Multiple Airlines
Find Deal

Everything you should know

When to travel
January
Cheapest • 35% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
Multiple Airlines
Tue 9/16
CHI - DSI • multi-stop
Cheapest one-way
Multiple Airlines
Tue 9/16
CHI - DSI • multi-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Destin!
Booking Insights

KAYAK's insights & trends for Chicago to Destin flights

Get data-powered insights and trends into flights from Chicago to Destin to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago to Destin?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Destin, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Destin is January, where tickets cost $256 (return) on average. On the other hand, the most expensive months are October and May, where the average cost of round-trip tickets is $510 and $493 respectively.

Good to know

Low seasonDecember
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 6% increase in price.

When to book flights from Chicago to Destin

Are your dates flexible? Find out the best times to travel from Chicago to Destin based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Destin

  • Do I need a passport to fly between Chicago and Destin?

    No

  • Which aircraft models fly most regularly from Chicago to Destin?

    We unfortunately don’t have that data for this specific route.

  • Which is the best airline for flights from Chicago to Destin, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Destin are Delta and United Airlines. With an average price for the route of $372 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $487 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Destin?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Destin.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Destin?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Destin from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Destin?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Destin with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Destin?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Destin from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Chicago to Destin

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Destin. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Destin? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 7954 reviews
7.9Entertainment
8.5Crew
8.2Boarding
7.3Food
7.9Comfort
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

The plane had originated in Las Vegas at 6:30 in the morning and flew to Moline where we boarded. The flight left around 12:30 PM and there were no boxed snacks available and many of the alcoholic beverages were unavailable. I would find it hard to believe that that many of the passengers coming from Las Vegas at 6:30 in the morning, drank and ate that much of the items. I can only come to the conclusion that someone failed to stock the plane for the round-trip. This is a huge revenue failure for the airline and disappointment for the passengers. The flight crew did not seem happy to be there and did not engage with passengers. Allegiant you can do better.

They did not let my husband on the plane with our service animal at the last minute. Do NOT fly this airline with a service animal!

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

Everything you need to know for your flight from Chicago to Destin

Information on your arrival and departure airports

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