--- title: "Chicago to Destin cheap flights (CHI to DSI) - Expedia" description: "Cheap Flights from Chicago (CHI) to Destin (DSI) start at for one-way and for round trip. Earn your airline miles on top of our rewards!" canonical: "https://www.expedia.com/lp/flights/chi/dsi/chicago-to-destin" language: en-US market: US currency: USD prices_as_of: 2026-11-14T01:59:02Z --- # Cheap Flights from Chicago (CHI) to Destin (DSI) ![A pier extending into the ocean at sunset.](https://images.trvl-media.com/place/130507/30fe1657-1799-467b-9142-0128c6925054.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Popular airlines from Chicago to Destin, FL (DSI-Destin-Fort Walton Beach) [American Airlines](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:DSI,departure:11/28/2026TANYT&leg2=from:DSI,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) [United](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:DSI,departure:11/28/2026TANYT&leg2=from:DSI,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) [Southwest Airlines](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:DSI,departure:11/28/2026TANYT&leg2=from:DSI,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) [Delta](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:DSI,departure:11/28/2026TANYT&leg2=from:DSI,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) [Frontier Airlines](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:DSI,departure:11/28/2026TANYT&leg2=from:DSI,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) [JetBlue Airways](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:DSI,departure:11/28/2026TANYT&leg2=from:DSI,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) [Alaska Airlines](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:DSI,departure:11/28/2026TANYT&leg2=from:DSI,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) ## Alternative airports near Destin Prices were available within the past 7 days. Prices and availability are subject to change. [Select flight to Northwest Florida Regional VPS. Cheapest option available. Average driving time to city center is 29 minutes. Flights from $235](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:VPS,departure:11/28/2026TANYT&leg2=from:VPS,to:MDW,departure:11/30/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 29 min ## Book with confidence ### Chicago to Destin Flights #### The cheapest times to fly from Chicago to Destin On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Destin are during the month of . You can find some of the cheapest flights from Chicago to Destin with Expedia's search tool and vast selection of airlines. #### The best time to book a flight from Chicago to Destin Sunday is one of the best days to book for cheap flights from Chicago to Destin: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance. #### How to find cheap round-trip tickets from Chicago to Destin Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Destin in 2026\. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members. Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Destin flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps. You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Chicago to Destin airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures. *\*Terms apply.* *Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages.* ## Travel information | Origin airport | Chicago, IL | | ------------------- | -------------------------------- | | Destination airport | Destin-Fort Walton Beach Airport | | Distance | 813 miles away | ## Explore a world of travel with Expedia - [Flights](?equalTargetTab=tab-0) - [Flights from Lafayette (LFT) to Destin (DSI)](https://www.expedia.com/lp/flights/lft/dsi/lafayette-to-destin) - [Flights from Las Vegas (LAS) to Destin (DSI)](https://www.expedia.com/lp/flights/las/dsi/las-vegas-to-destin) - [Flights from Knoxville (TYS) to Destin (DSI)](https://www.expedia.com/lp/flights/tys/dsi/knoxville-to-destin) - [Flights from Fort Wayne (FWA) to Destin (DSI)](https://www.expedia.com/lp/flights/fwa/dsi/fort-wayne-to-destin) - [Flights from Fort Myers (RSW) to Destin (DSI)](https://www.expedia.com/lp/flights/rsw/dsi/fort-myers-to-destin) - [Flights from Des Moines (DSM) to Destin (DSI)](https://www.expedia.com/lp/flights/dsm/dsi/des-moines-to-destin) - [Flights from Dallas (DFW) to Fort Walton Beach (VPS)](https://www.expedia.com/lp/flights/dfw/vps/dallas-to-fort-walton-beach) - [Flights from Indianapolis (IND) to Destin (DSI)](https://www.expedia.com/lp/flights/ind/dsi/indianapolis-to-destin) - [Flights from Houston (HOU) to Destin (DSI)](https://www.expedia.com/lp/flights/hou/dsi/houston-to-destin) - [Flights from White Plains (HPN) to Destin (DSI)](https://www.expedia.com/lp/flights/hpn/dsi/white-plains-to-destin) - [Flights from Miami (MIA) to Destin (DSI)](https://www.expedia.com/lp/flights/mia/dsi/miami-to-destin) - [Flights from St. Petersburg (PIE) to Destin (DSI)](https://www.expedia.com/lp/flights/pie/dsi/st-petersburg-to-destin) - [Flights from Minneapolis (MSP) to Fort Walton Beach (VPS)](https://www.expedia.com/lp/flights/msp/vps/minneapolis-to-fort-walton-beach) - [Flights from Tulsa (TUL) to Destin (DSI)](https://www.expedia.com/lp/flights/tul/dsi/tulsa-to-destin) - [Flights from Cedar Rapids (CID) to Destin (DSI)](https://www.expedia.com/lp/flights/cid/dsi/cedar-rapids-to-destin) - [Flights from Grand Rapids (GRR) to Destin (DSI)](https://www.expedia.com/lp/flights/grr/dsi/grand-rapids-to-destin) - [Flights from Montgomery (MGM) to Destin (DSI)](https://www.expedia.com/lp/flights/mgm/dsi/montgomery-to-destin) - [Flights from Minneapolis (MSP) to Destin (DSI)](https://www.expedia.com/lp/flights/msp/dsi/minneapolis-to-destin) - [Flights from Houston (IAH) to Destin (DSI)](https://www.expedia.com/lp/flights/iah/dsi/houston-to-destin) - [Flights from St. Louis (STL) to Destin (DSI)](https://www.expedia.com/lp/flights/stl/dsi/st-louis-to-destin) - [Flights from Columbia (CAE) to Destin (DSI)](https://www.expedia.com/lp/flights/cae/dsi/columbia-to-destin) - [Flights from Cincinnati (CVG) to Destin (DSI)](https://www.expedia.com/lp/flights/cvg/dsi/cincinnati-to-destin) - [Flights from Newark Liberty Intl. Airport (EWR) to Destin (DSI)](https://www.expedia.com/lp/flights/ewr/dsi/newark-liberty-intl-airport-to-destin) - [Flights from Myrtle Beach (MYR) to Destin (DSI)](https://www.expedia.com/lp/flights/myr/dsi/myrtle-beach-to-destin) - [Flights from Boston (BOS) to Destin (DSI)](https://www.expedia.com/lp/flights/bos/dsi/boston-to-destin) - [Flights from Tampa (TPA) to Destin (DSI)](https://www.expedia.com/lp/flights/tpa/dsi/tampa-to-destin) - [Flights from Wichita (ICT) to Destin (DSI)](https://www.expedia.com/lp/flights/ict/dsi/wichita-to-destin) - [Flights from Orlando (MCO) to Destin (DSI)](https://www.expedia.com/lp/flights/mco/dsi/orlando-to-destin) - [Flights from Pittsburgh (PIT) to Destin (DSI)](https://www.expedia.com/lp/flights/pit/dsi/pittsburgh-to-destin) - [Flights from Rochester (ROC) to Destin (DSI)](https://www.expedia.com/lp/flights/roc/dsi/rochester-to-destin) - [Flights from Chicago (ORD) to Destin (DSI)](https://www.expedia.com/lp/flights/ord/dsi/chicago-to-destin) - [Flights from Peoria (PIA) to Destin (DSI)](https://www.expedia.com/lp/flights/pia/dsi/peoria-to-destin) - [Flights from Charleston (CHS) to Destin (DSI)](https://www.expedia.com/lp/flights/chs/dsi/charleston-to-destin) - [Flights from Charlotte (CLT) to Destin (DSI)](https://www.expedia.com/lp/flights/clt/dsi/charlotte-to-destin) - [Flights from New Orleans (MSY) to Destin (DSI)](https://www.expedia.com/lp/flights/msy/dsi/new-orleans-to-destin) - [Flights from Belleville (BLV) to Destin (DSI)](https://www.expedia.com/lp/flights/blv/dsi/belleville-to-destin) - [Flights from Springfield (SGF) to Destin (DSI)](https://www.expedia.com/lp/flights/sgf/dsi/springfield-to-destin) - [Flights from Washington (DCA) to Destin (DSI)](https://www.expedia.com/lp/flights/dca/dsi/washington-to-destin) - [Flights from Omaha (OMA) to Destin (DSI)](https://www.expedia.com/lp/flights/oma/dsi/omaha-to-destin) - [Flights from Panama City (PTY) to Destin (DSI)](https://www.expedia.com/lp/flights/pty/dsi/panama-city-to-destin) - [Flights from Albany (ALB) to Destin (DSI)](https://www.expedia.com/lp/flights/alb/dsi/albany-to-destin) - [Flights from Panama City (ECP) to Destin (DSI)](https://www.expedia.com/lp/flights/ecp/dsi/panama-city-to-destin) - [Flights from Mobile (BFM) to Destin (DSI)](https://www.expedia.com/lp/flights/bfm/dsi/mobile-to-destin) - [Flights from Savannah (SAV) to Destin (DSI)](https://www.expedia.com/lp/flights/sav/dsi/savannah-to-destin) - [Flights from Boston (BOS) to Fort Walton Beach (VPS)](https://www.expedia.com/lp/flights/bos/vps/boston-to-fort-walton-beach) - [Flights from Los Angeles (LAX) to Destin (DSI)](https://www.expedia.com/lp/flights/lax/dsi/los-angeles-to-destin) - [Flights from Toledo (TOL) to Destin (DSI)](https://www.expedia.com/lp/flights/tol/dsi/toledo-to-destin) - [Flights from Detroit (DTW) to Destin (DSI)](https://www.expedia.com/lp/flights/dtw/dsi/detroit-to-destin) - [Flights from Syracuse (SYR) to Destin (DSI)](https://www.expedia.com/lp/flights/syr/dsi/syracuse-to-destin) - [Flights from Hartford (BDL) to Destin (DSI)](https://www.expedia.com/lp/flights/bdl/dsi/hartford-to-destin) - [Flights from Bloomington (BMI) to Destin (DSI)](https://www.expedia.com/lp/flights/bmi/dsi/bloomington-to-destin) - [Flights from West Palm Beach (PBI) to Destin (DSI)](https://www.expedia.com/lp/flights/pbi/dsi/west-palm-beach-to-destin) - [Flights from Louisville (SDF) to Fort Walton Beach (VPS)](https://www.expedia.com/lp/flights/sdf/vps/louisville-to-fort-walton-beach) - [Flights from Louisville (SDF) to Destin (DSI)](https://www.expedia.com/lp/flights/sdf/dsi/louisville-to-destin) - [Flights from Raleigh (RDU) to Destin (DSI)](https://www.expedia.com/lp/flights/rdu/dsi/raleigh-to-destin) - [Flights from Sarasota (SRQ) to Destin (DSI)](https://www.expedia.com/lp/flights/srq/dsi/sarasota-to-destin) - [Flights from Little Rock (LIT) to Destin (DSI)](https://www.expedia.com/lp/flights/lit/dsi/little-rock-to-destin) - [Flights from Salt Lake City (SLC) to Destin (DSI)](https://www.expedia.com/lp/flights/slc/dsi/salt-lake-city-to-destin) - [Flights from Phoenix (PHX) to Destin (DSI)](https://www.expedia.com/lp/flights/phx/dsi/phoenix-to-destin) - [Flights from Tallahassee (TLH) to Destin (DSI)](https://www.expedia.com/lp/flights/tlh/dsi/tallahassee-to-destin) - [Flights from Greenville (GSP) to Destin (DSI)](https://www.expedia.com/lp/flights/gsp/dsi/greenville-to-destin) - [Flights from Cleveland (CLE) to Destin (DSI)](https://www.expedia.com/lp/flights/cle/dsi/cleveland-to-destin) - [Flights from Kansas City (MCI) to Destin (DSI)](https://www.expedia.com/lp/flights/mci/dsi/kansas-city-to-destin) - [Flights from Greensboro (GSO) to Destin (DSI)](https://www.expedia.com/lp/flights/gso/dsi/greensboro-to-destin) - [Flights from Richmond (RIC) to Destin (DSI)](https://www.expedia.com/lp/flights/ric/dsi/richmond-to-destin) - [Flights from Seattle (SEA) to Destin (DSI)](https://www.expedia.com/lp/flights/sea/dsi/seattle-to-destin) - [Flights from Milwaukee (MKE) to Destin (DSI)](https://www.expedia.com/lp/flights/mke/dsi/milwaukee-to-destin) - [Flights from Columbus (CMH) to Destin (DSI)](https://www.expedia.com/lp/flights/cmh/dsi/columbus-to-destin) - [Flights from Lexington (LEX) to Destin (DSI)](https://www.expedia.com/lp/flights/lex/dsi/lexington-to-destin) - [Flights from Philadelphia (PHL) to Destin (DSI)](https://www.expedia.com/lp/flights/phl/dsi/philadelphia-to-destin) - [Flights from Huntsville (HSV) to Destin (DSI)](https://www.expedia.com/lp/flights/hsv/dsi/huntsville-to-destin) - [Flights from Nashville (BNA) to Destin (DSI)](https://www.expedia.com/lp/flights/bna/dsi/nashville-to-destin) - [Flights from Fayetteville (XNA) to Destin (DSI)](https://www.expedia.com/lp/flights/xna/dsi/fayetteville-to-destin) - [Flights from Gainesville (GNV) to Destin (DSI)](https://www.expedia.com/lp/flights/gnv/dsi/gainesville-to-destin) - [Flights from Madison (MSN) to Destin (DSI)](https://www.expedia.com/lp/flights/msn/dsi/madison-to-destin) - [Flights from San Antonio (SAT) to Destin (DSI)](https://www.expedia.com/lp/flights/sat/dsi/san-antonio-to-destin) - [Flights from Shreveport (SHV) to Destin (DSI)](https://www.expedia.com/lp/flights/shv/dsi/shreveport-to-destin) - [Flights from Pensacola (PNS) to Destin (DSI)](https://www.expedia.com/lp/flights/pns/dsi/pensacola-to-destin) - [Flights from San Francisco (SFO) to Destin (DSI)](https://www.expedia.com/lp/flights/sfo/dsi/san-francisco-to-destin) - [Flights from Oklahoma City (OKC) to Destin (DSI)](https://www.expedia.com/lp/flights/okc/dsi/oklahoma-city-to-destin) - [Flights from Tri-Cities (TRI) to Destin (DSI)](https://www.expedia.com/lp/flights/tri/dsi/tri-cities-to-destin) - [Flights from Asheville (AVL) to Destin (DSI)](https://www.expedia.com/lp/flights/avl/dsi/asheville-to-destin) - [Flights from Chicago (MDW) to Destin (DSI)](https://www.expedia.com/lp/flights/mdw/dsi/chicago-to-destin) - [Flights from Allentown (ABE) to Destin (DSI)](https://www.expedia.com/lp/flights/abe/dsi/allentown-to-destin) - [Flights from Atlanta (ATL) to Destin (DSI)](https://www.expedia.com/lp/flights/atl/dsi/atlanta-to-destin) - [Flights from New York (JFK) to Destin (DSI)](https://www.expedia.com/lp/flights/jfk/dsi/new-york-to-destin) - [Flights from Memphis (MEM) to Destin (DSI)](https://www.expedia.com/lp/flights/mem/dsi/memphis-to-destin) - [Flights from Chattanooga (CHA) to Destin (DSI)](https://www.expedia.com/lp/flights/cha/dsi/chattanooga-to-destin) - [Flights from Washington (IAD) to Destin (DSI)](https://www.expedia.com/lp/flights/iad/dsi/washington-to-destin) - [Flights from Baltimore (BWI) to Destin (DSI)](https://www.expedia.com/lp/flights/bwi/dsi/baltimore-to-destin) - [Flights from Dallas (DFW) to Destin (DSI)](https://www.expedia.com/lp/flights/dfw/dsi/dallas-to-destin) - [Flights from Baton Rouge (BTR) to Destin (DSI)](https://www.expedia.com/lp/flights/btr/dsi/baton-rouge-to-destin) - [Flights from Birmingham (BHM) to Destin (DSI)](https://www.expedia.com/lp/flights/bhm/dsi/birmingham-to-destin) - [Flights from Fort Lauderdale (FLL) to Destin (DSI)](https://www.expedia.com/lp/flights/fll/dsi/fort-lauderdale-to-destin) - [Flights from Dayton (DAY) to Destin (DSI)](https://www.expedia.com/lp/flights/day/dsi/dayton-to-destin) - [Flights from Jacksonville (OAJ) to Destin (DSI)](https://www.expedia.com/lp/flights/oaj/dsi/jacksonville-to-destin) - [Flights from Akron (CAK) to Destin (DSI)](https://www.expedia.com/lp/flights/cak/dsi/akron-to-destin) - [Flights from San Diego (SAN) to Destin (DSI)](https://www.expedia.com/lp/flights/san/dsi/san-diego-to-destin) - [Flights from Denver (DEN) to Destin (DSI)](https://www.expedia.com/lp/flights/den/dsi/denver-to-destin) - [Flights from Clearwater (CLW) to Destin (DSI)](https://www.expedia.com/lp/flights/clw/dsi/clearwater-to-destin) \*Available to One Key members. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/lp/flights/chi/dsi/chicago-to-destin en-IN: https://www.expedia.co.in/lp/flights/chi/dsi/chicago-to-destin en-US: https://www.expedia.com/lp/flights/chi/dsi/chicago-to-destin es: https://www.expedia.com/es/lp/vuelos/chi/dsi/todos-los-aeropuertos-de-chicago-a-destin es-ES: https://www.expedia.es/lp/vuelos/chi/dsi/chicago-a-destin zh-CN: https://www.expedia.com/cn/lp/flights/chi/dsi/chicago-to-destin nb-NO: https://www.expedia.no/lp/fly/chi/dsi/chicago-til-destin en-CA: https://www.expedia.ca/lp/flights/chi/dsi/chicago-to-destin ar: https://www.expedia.sa/lp/flights/chi/dsi/chicago-to-destin en-PH: https://www.expedia.com.ph/lp/flights/chi/dsi/chicago-to-destin ```