Cheap Flights from Key West International to Chicago

Return selected
Return selected
origin
Enter the city you're flying from, or choose from the options below
Include nearby airports
    selected
    destination
    . Enter your destination, or choose from the options below
    Include nearby airports
      selected
      Travellers and cabin class, 1 Adult, Economy
      American Airlines
      United
      Air New Zealand

      Compare Key West International to Chicago flight deals

      Find the cheapest month or even day of the year to fly to Chicago

      Book the best Chicago fare with no extra fees

      Flight deals from Key West International to Chicago

      Looking for a cheap last-minute deal or the best return flight from Key West International Airport to Chicago? If you want to travel next month, return fares start from $553. Find the lowest prices on one-way and return tickets right here.

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

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Key West International to Chicago flights are currently cheapest in January.

      Direct flights from Key West International to Chicago

      Air New Zealand
      American Airlines
      United

      Alternative Key West International to Chicago routes

      Looking for the cheapest, fastest or easiest route from Key West International to Chicago? You could fly into the following airports instead.

      Key West to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found$538
      Cheapest month to flyJanuary
      Average flight time3 hrs, 45 mins
      Most popular airlineAmerican Airlines
      Average flights per week33

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

      There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
      The best price we found for a return flight from Key West International to Chicago is $538. 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.
      3 hours and 45 minutes is the average flight time from Key West International to Chicago.
      American Airlines, United and Air New Zealand fly direct from Key West International to Chicago.
      As of August 2026, there are 33 flights per week flying from Key West International to Chicago.
      The cheapest month to fly from Key West International to Chicago is usually January.
      If you're flying from Key West International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from $538.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Key West International Airport to Chicago on Friday, 8 January 2027.
      Yes – the average flight time is 3 hours and 45 minutes.
      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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      In August, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
      Currently, United offers the cheapest flight tickets to Chicago.

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

      • Expect to be in the air for 3 hours 20 minutes. On average, that's the duration of a direct flight from Key West International Airport to Chicago.

      • The timezone in Chicago is UTC-6. The city is one hour behind Key West, where Key West International Airport is located.

      • The most popular route is from Key West International Airport (EYW) to Chicago O'Hare International Airport (ORD). You can choose from 18 weekly services between these two airports. If you want to get going as soon as possible, the earliest flight from EYW to ORD is the 07:00 United Airlines option. If you prefer to leave later in the day, the final departure is at 16:05 with United Airlines.

      • Give yourself plenty of time to get on your EYW to Chicago flight. A good rule of thumb is to arrive two hours before international departures and an hour ahead for domestic flights.

      • During popular months such as March, it's wise to get to the airport earlier than usual. Arrive two hours before domestic departures and four hours ahead for an international flight when you fly during a peak period in general.

      • Direct Key West International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) will be where your journey ends.

      • Book your ticket with United Airlines. This popular carrier offers direct flights from Key West International Airport to Chicago.

      • Travelling from central Key West to EYW takes around 20 minutes by public transport. If you drive, ride-share or take a taxi, you'll cover the 3 kilometres in 10 minutes or so, depending on traffic.

      • Want a relaxed start to your trip? Stay near EYW. Whether you're boarding an early flight from Key West International Airport to Chicago or want to avoid feeling rushed, these hotels are a convenient choice:

      • When it comes to the on-time performance of Key West International Airport, data shows 75% of flights arrive within the expected time frame.

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

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

      • The best price we've found for a one-way Key West International Airport to Chicago flight is $254. The cheapest price for a return flight is $538. Keep in mind fares can change due to availability at the time of booking.

      • Booking in advance is often the key to securing a cheap flight from EYW to Chicago. Airlines adjust prices based on demand, so the closer your departure date, the more expensive your ticket may be.

      • Finding cheap tickets from Key West International Airport to Chicago is easier if you're flexible with your dates. Use the 'Whole month' search function to get the lowest prices across each month and score an awesome deal.

      • There's no need to check in daily to find out if fares have dropped when you create a Price Alert. We'll let you know as soon as there's an extra saving on cheap flights from EYW to Chicago.

      • Snag an affordable flight from Key West International Airport to Chicago with the help of our filters. Choose your preferred departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

      Airports in Chicago

      Chicago O'Hare International Airport (ORD)

      • The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It takes about 30 minutes to reach the centre driving.

      • If you're travelling on public transport, expect a journey time of around 45 minutes.

      • The last thing you need is a lengthy journey to your hotel if you're getting in late on a flight from Key West International Airport to Chicago. Reserve one of these accommodation options near ORD instead:

      • To lock in the lowest price, book your ride from Chicago O'Hare International Airport about four weeks in advance of your flight from EYW to Chicago.

      • The street address for ORD is 10000 West O'Hare.

      Chicago Midway International Airport (MDW)

      • Central Chicago is about 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Key West International Airport to Chicago has touched down and you've navigated your way to arrivals, the drive should take about 25 minutes.

      • Travelling by public transport will take around 30 minutes.

      • There are some great places to call home for the night near MDW. Kick back and get cosy after your EYW to Chicago flight at one of these well-located options:

      • Get what you want, not just what's left over. Reserving your ride from MDW four weeks in advance often means lower prices and a bigger choice of vehicles.

      • Chicago Midway International Airport can be found at 5700 South Cicero.

      Chicago Rockford International Airport (RFD)

      • Step off your flight from Key West International Airport to Chicago and go straight to your hotel or jump right into exploring. The centre of Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 40 minutes to drive there.

      • If you go by public transport, the journey will take you around 2 hours.

      • Stay at a hotel close to RFD and get from baggage claim to bedtime in a flash. Whether you're arriving on a late EYW to Chicago flight or just want a stress-free arrival, these stays will have you settling in quickly:

      • Rental agencies sometimes offer promotions for early bookings, so secure your vehicle from RFD ahead of your flight from Key West International Airport to Chicago. A little planning can save you money.

      • Chicago Rockford International Airport's address is 2 Airport Cir.

      Best time to go to Chicago

      • It's time to plan your trip dates for your flight from Key West International Airport to Chicago. July is the busiest month for a trip to Chicago. If you want a more low-key vibe, go in January.

      • Lock in a Key West International Airport to Chicago plane ticket with a departure in July to experience the city during its warmest month. Expect temperatures to range from 16ºC to 28ºC.

      • Look for cheap tickets from EYW to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

      More about Chicago

      Explore more of the United States

      • Columbus is just one of the many places in the United States waiting to be explored once you've seen Chicago. Around 451 kilometres away to the southeast, check out popular attractions including Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Indianapolis is another well-known destination in the United States and is around 257 kilometres southeast of Chicago. No journey is complete without visiting Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

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