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Cheap Flights from Chicago Midway to Key West International

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      Travellers and cabin class, 1 Adult, Economy

      Compare Chicago Midway to Key West International flight deals

      Find the cheapest month or even day of the year to fly to Key West International

      Book the best Key West International fare with no extra fees

      Flight deals from Chicago Midway to Key West International

      Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Key West International Airport? If you want to travel next month, return fares start from $690. Find the lowest prices on one-way and return tickets right here.
      Key West.$610 per passenger.Departing Fri, 8 Jan, returning Thu, 14 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 8 Jan, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Thu, 14 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $610, select.
      Key West.$612 per passenger.Departing Sat, 14 Nov, returning Wed, 18 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 14 Nov, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Wed, 18 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $612, select.
      Key West.$645 per passenger.Departing Tue, 11 May, returning Tue, 18 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 11 May, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Tue, 18 May, arriving in Chicago Midway.Price includes taxes and charges.From $645, select.
      Key West.$666 per passenger.Departing Fri, 16 Apr, returning Tue, 20 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 16 Apr, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Tue, 20 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $666, select.
      Key West.$690 per passenger.Departing Mon, 19 Oct, returning Sat, 24 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 19 Oct, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Sat, 24 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $690, select.
      Key West.$741 per passenger.Departing Thu, 17 Dec, returning Fri, 25 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 17 Dec, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Fri, 25 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $741, select.
      Key West.$747 per passenger.Departing Fri, 27 Nov, returning Wed, 2 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 27 Nov, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Wed, 2 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $747, select.
      Key West.$850 per passenger.Departing Sat, 20 Feb, returning Fri, 26 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 20 Feb, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Fri, 26 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $850, select.
      Key West.$866 per passenger.Departing Fri, 18 Sep, returning Tue, 22 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 18 Sep, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Tue, 22 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $866, select.
      Key West.$1,019 per passenger.Departing Fri, 30 Oct, returning Tue, 3 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 30 Oct, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Tue, 3 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $1,019, select.
      Key West.$1,038 per passenger.Departing Sat, 13 Mar, returning Sat, 20 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 13 Mar, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Sat, 20 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $1,038, select.
      Key West.$1,211 per passenger.Departing Sun, 6 Jun, returning Fri, 11 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sun, 6 Jun, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Fri, 11 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $1,211, select.
      Key West.$1,295 per passenger.Departing Fri, 26 Mar, returning Fri, 2 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 26 Mar, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Fri, 2 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $1,295, select.
      Key West.$1,832 per passenger.Departing Thu, 31 Dec, returning Sun, 3 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 31 Dec, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Sun, 3 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $1,832, select.

      Find the cheapest month to fly from Chicago Midway to Key West International

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Key West International flights are currently cheapest in January.
      Sep
      from $866
      Oct
      from $690
      Nov
      from $612
      Dec
      from $741
      Jan
      from $610
      Feb
      from $850
      Mar
      from $1,038
      Apr
      from $666
      May
      from $645
      Jun
      from $1,211
      Jul
      Find prices
      Aug
      Find prices

      Chicago Midway to Key West International: Alternative routes

      Compare routes from Chicago Midway to Key West below. You may find an airport to fly into that's cheaper, faster, or easier than Key West International.

      Key West International

      5km from central Key West
      ClosestCheapest
      from $610
      Search flights

      Chicago to Key West: Flight information

      The things to know before you go.
      Cheapest flight found$610
      Cheapest month to flyJanuary

      Finding cheap flights from Chicago Midway to Key West International: Frequently asked questions

      The best price we found for a return flight from Chicago Midway to Key West International is $610. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      Currently, there are no airlines that fly direct from Chicago Midway to Key West International. But we found flights with one or more stops from $610.
      As of September 2026, there are no flights flying from Chicago Midway to Key West International.
      The cheapest month to fly from Chicago Midway to Key West International is usually January.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Key West International Airport on Friday, 8 January 2027.
      No airlines currently offer direct flights between Chicago Midway Airport and Key West International Airport. Most routes have one or more stops.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Key West International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Key West is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Delta offers the cheapest flight tickets to Key West International.

      Travelling from Chicago Midway Airport (MDW) to Key West International Airport (EYW): what you need to know

      • To ensure you catch your MDW to EYW flight, leave plenty of time to navigate the airport and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the general travel rule.

      • Flying during a peak month such as July? Public holidays and other high seasons can mean longer lines and delays at check-in and security. Be extra cautious and arrive up to four hours before an international flight and two hours before a domestic departure.

      • We make it a piece of cake to book a flight with a stopover. To see all your options for tickets from Chicago Midway Airport to Key West International Airport, deselect 'Direct flights only.' Then, pick a flight that has a stop long enough to visit your chosen city. Worthwhile stopovers between MDW and EYW include:

        • Atlanta Hartsfield-Jackson Airport

        • Miami International Airport

        • Tampa International Airport

      How to find the cheapest flights from Chicago Midway Airport (MDW) to Key West International Airport (EYW)

      • The lowest price we've found for a one-way Chicago Midway Airport to Key West International Airport flight is $525. A return plane ticket right now is $610. Depending on the availability when you book, these fares can change.

      • Don't leave things to the last minute. You're more likely to find cheap tickets from MDW to EYW if you book ahead. Airlines often have some excellent early bird deals.

      • The 'Whole month' tool shows you the cheapest flights from Chicago Midway Airport to Key West International Airport throughout the entire month. It's a good way to find a bargain if your travel plans aren't set in stone.

      • Never miss a deal on cheap flights from MDW to EYW by creating a Price Alert. We'll send you an email or notification through the app when fares go down.

      • Select your preferred departure and arrival times, number of stops and airlines with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Chicago Midway Airport to Key West International Airport.

      Handy information about Chicago Midway Airport (MDW)

      • MDW's address is 5700 South Cicero.

      • 76% of flights taking off from Chicago Midway Airport reach their destination on schedule.

      • Chicago Midway Airport is around 16 kilometres from central Chicago. If you're ride-sharing, catching a taxi or driving from the centre, it'll take 25 minutes or so to arrive, depending on the traffic.

      • The trip when using public transport takes roughly 30 minutes.

      • Catching an early flight from Chicago Midway Airport to Key West International Airport? Avoid rushing to the airport (and catch some extra z's) by picking one of these stays close to MDW:

      Arriving at Key West International Airport (EYW)

      Getting from Key West International Airport (EYW) to central Key West

      • You'll find EYW at 3491 South Roosevelt Boulevard.

      • Key West International Airport is roughly 5 kilometres from central Key West. The drive time takes around 10 minutes.

      • It typically takes 20 minutes if you're travelling by public transport.

      When to fly to Key West International Airport (EYW)

      • It's time to work out your trip dates for your flight from Chicago Midway Airport to Key West International Airport. April is the most popular month to visit Key West. If you'd like a more relaxed vibe, go in September.

      • The warmest month in Key West is August, with temperatures ranging between 26ºC and 30ºC. Book your flights from Chicago Midway Airport to Key West International Airport in this month if this is the type of weather you enjoy.

      • Look for cheap tickets from MDW to EYW in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between 18ºC and 23ºC on average.

      Explore more of the United States

      • You've visited Key West, now it's time to discover more of the United States. Travel around 209 kilometres north-east to Miami to tick off its leading sights. From Beach to Ocean Drive and Port of Miami, you'll have a packed itinerary ahead.

      • Tampa is another standout destination in the United States and is around 386 kilometres north of Key West. No trip is complete without dropping by Busch Gardens Tampa, The Florida Aquarium and ZooTampa at Lowry Park.

      More travel options

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.