Cheap Flights from Key West International to Chicago O'Hare International

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Find the cheapest month to fly from Key West International to Chicago O'Hare International

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 O'Hare International flights are currently cheapest in May.

Direct flights from Key West International to Chicago O'Hare International

Key West International to Chicago O'Hare International: Alternative routes

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

Key West to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 5,792
Cheapest month to flyMay
Average flight time3 hrs, 33 mins
Most popular airlineQatar Airways
Average flights per week22

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

The best price we found for a return flight from Key West International to Chicago O'Hare International is R 6,018. 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 33 minutes is the average flight time from Key West International to Chicago O'Hare International.
Qatar Airways, Envoy Air and American Airlines fly direct from Key West International to Chicago O'Hare International.
As of April 2025, there are 22 flights per week flying from Key West International to Chicago O'Hare International.
The cheapest month to fly from Key West International to Chicago O'Hare International is usually April 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Key West International Airport to Chicago O'Hare International Airport on Wednesday, 28 May 2025.
Yes – the average flight time is 3 hours and 33 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 O'Hare 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Delta and United offer the cheapest flight tickets to Chicago O'Hare International.

Flying from Key West International Airport (EYW) to O'Hare International Airport (ORD): what you need to know

  • Book a direct flight from Key West International Airport to O'Hare International Airport and you'll be travelling for an average of 3 hours 30 minutes.

  • Chicago is one hour behind Key West and is in the UTC-5 timezone.

  • Every week, there are seven Key West International Airport to O'Hare International Airport flights. To be on board as early as possible, go for the 12:15 United Airlines flight. If you'd rather make the most of your day before you fly, the latest flight is at 16:05 with United Airlines.

  • Your EYW to ORD flight won't wait if you're late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

  • You can expect bigger queues during popular months like January. Arriving up to four hours in advance for international flights and two hours for a domestic departure is a wise move.

  • Jetting into Chicago (and then exploring more of United States!) is easy with American Airlines. This popular airline has direct flights from Key West International Airport to O'Hare International Airport.

  • The majority of travellers choose to fly with American Airlines on this route.

  • American Airlines is the most punctual carrier operating EYW to ORD flights. A dependable 81.67% of its services on this route land on time.

  • We make it simple to book a flight with a stopover. To see your options for tickets from Key West International Airport to O'Hare International Airport, deselect 'Direct flights only.' Then, pick a flight offering a stop long enough to tour the city of your choice. Stopovers between EYW and ORD include:

    • Hartsfield-Jackson Atlanta International Airport

    • Asheville Regional Airport

    • Cincinnati/Northern Kentucky Airport

How to find the cheapest flights from Key West International Airport (EYW) to O'Hare International Airport (ORD)

  • Right now, R 5,792 is the cheapest price we've seen for a one-way Key West International Airport to O'Hare International Airport flight. The best price for a return plane ticket is R 6,018. Keep in mind that fares could change due to availability at the time of booking.

  • Score cheap tickets from EYW to ORD by booking one month ahead. Based on our research, that's the sweet spot for bagging a bargain.

  • The cheapest month for flights from Key West International Airport to O'Hare International Airport is December. Use the 'Whole month' tool to see the lowest airfares if you have flexible dates.

  • You won't have to check back in every day to see if fares have dropped when you set up a Price Alert. We'll let you know as soon as there's a change in price on cheap flights from EYW to ORD.

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

Handy information about Key West International Airport (EYW)

  • The address for EYW is 3491 South Roosevelt Boulevard.

  • When it comes to the on-time performance of Key West International Airport, 71.92% of flights meet their scheduled arrival time.

  • Central Key West to Key West International Airport is approximately 3 kilometres. Depending on traffic, it'll take about 5 minutes to get there if you're ride-sharing, catching a cab or driving.

  • The trip when using public transport will take about 40 minutes.

  • Get your travels off to a relaxed start by staying near EYW. Whether you're boarding an early flight from Key West International Airport to O'Hare International Airport or want to avoid feeling rushed, these hotels are the answer:

Arriving at O'Hare International Airport (ORD)

Getting from O'Hare International Airport (ORD) to central Chicago

  • ORD is located at 10000 West O'Hare.

  • O'Hare International Airport to central Chicago has a drive time of around 35 minutes. It's approximately 40 kilometres away.

  • Travelling to the centre on public transport typically takes 55 minutes.

When to fly to O'Hare International Airport (ORD)

  • It's time to work out your travel dates for your flight from Key West International Airport to O'Hare International Airport. August is the most popular month to head to Chicago. If you'd like a more low-key vibe, go in January.

  • When reserving your flight from Key West International Airport to O'Hare International Airport, consider the type of weather you like. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • If you want cooler conditions, search for a cheap ticket from EYW to ORD in January. Temperatures average between -12ºC (10ºF) and 3ºC (37ºF) then.

Explore more of United States

  • You've visited Chicago, now it's time to explore other corners of United States. Travel around 451 kilometres south-east to Columbus to check off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you busy.

  • If you're interested in discovering another major stop in United States, head for Indianapolis, about 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are key highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.