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Cheap flight tickets from Key West International to Chicago

Compare Key West International to Chicago flight deals

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Flight deals from Key West International Airport 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 RM718. Find the lowest prices on one-way and return tickets right here.
Chicago.RM717 per passenger.Departing Fri, 20 Feb, returning Mon, 2 Mar.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Fri, 20 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 2 Mar, arriving in Key West International.Price includes taxes and charges.From RM717, select.
Chicago.RM718 per passenger.Departing Fri, 20 Feb, returning Sun, 22 Feb.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Fri, 20 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sun, 22 Feb, arriving in Key West International.Price includes taxes and charges.From RM718, select.
Chicago.RM720 per passenger.Departing Thu, 5 Mar, returning Sun, 8 Mar.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Thu, 5 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sun, 8 Mar, arriving in Key West International.Price includes taxes and charges.From RM720, select.
Chicago.RM822 per passenger.Departing Tue, 24 Mar, returning Wed, 8 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Tue, 24 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 8 Apr, arriving in Key West International.Price includes taxes and charges.From RM822, select.
Chicago.RM856 per passenger.Departing Wed, 8 Apr, returning Fri, 10 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Wed, 8 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Fri, 10 Apr, arriving in Key West International.Price includes taxes and charges.From RM856, select.
Chicago.RM1,172 per passenger.Departing Fri, 24 Apr, returning Thu, 14 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Fri, 24 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Thu, 14 May, arriving in Key West International.Price includes taxes and charges.From RM1,172, select.
Chicago.RM1,274 per passenger.Departing Wed, 18 Mar, returning Wed, 25 Mar.Return flight with United.Outbound direct flight with United departs from Key West International on Wed, 18 Mar, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 25 Mar, arriving in Key West International.Price includes taxes and charges.From RM1,274, select.
Chicago.RM1,394 per passenger.Departing Fri, 8 May, returning Thu, 14 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Fri, 8 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Thu, 14 May, arriving in Key West International.Price includes taxes and charges.From RM1,394, select.
Chicago.RM1,507 per passenger.Departing Thu, 13 Aug, returning Mon, 24 Aug.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Thu, 13 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 24 Aug, arriving in Key West International.Price includes taxes and charges.From RM1,507, select.
Chicago.RM1,643 per passenger.Departing Thu, 5 Feb, returning Sun, 8 Feb.Return flight with United.Outbound direct flight with United departs from Key West International on Thu, 5 Feb, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 8 Feb, arriving in Key West International.Price includes taxes and charges.From RM1,643, select.
Chicago.RM1,941 per passenger.Departing Thu, 16 Jul, returning Thu, 23 Jul.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Thu, 16 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Thu, 23 Jul, arriving in Key West International.Price includes taxes and charges.From RM1,941, select.
Chicago.RM1,978 per passenger.Departing Sun, 31 May, returning Mon, 15 Jun.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Key West International on Sun, 31 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 15 Jun, arriving in Key West International.Price includes taxes and charges.From RM1,978, select.

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 February.
Jan
Find prices
Feb
from RM718
Mar
from RM720
Apr
from RM856
May
from RM1,394
Jun
from RM2,056
Jul
from RM1,941
Aug
from RM1,507
Sep
Find prices
Oct
Find prices
Nov
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Dec
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Direct flights from Key West International to Chicago

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.

Chicago Midway

14km from central Chicago
Closest
from RM1,053
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from RM717
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

Key West to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRM717
Cheapest month to flyFebruary
Average flight time3 hrs, 42 mins
Most popular airlineEnvoy Air
Average flights per week84

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Key West International to Chicago is RM717. 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 42 minutes is the average flight time from Key West International to Chicago.
Envoy Air, American Airlines and United fly direct from Key West International to Chicago.
As of January 2026, there are 84 flights per week flying from Key West International to Chicago.
The cheapest month to fly from Key West International to Chicago is usually February.
If you're flying from Key West International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from RM717.
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, 20 February 2026.
Yes – the average flight time is 3 hours and 42 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 January, the average temperature is usually around -4°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, Spirit Airlines and United offer 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 15 minutes. That's the average time for a direct flight from Key West International Airport to Chicago.

  • Chicago is one hour behind Key West, where Key West International Airport is located. Chicago observes the UTC-5 timezone.

  • With eight flights a week between the two airports, Key West International Airport (EYW) to O'Hare International Airport (ORD) is the busiest route. Catch United Airlines's 07:00 flight to get your trip from EYW to ORD underway.

  • For stress-free travel, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to board your EYW to Chicago flight.

  • Delays at check-in and security are likely if you're flying during high season, so give yourself some extra breathing room. A good rule of thumb for peak times? Get there up to four hours early for international flights and two hours for domestic departures.

  • You can book a direct Key West International Airport to Chicago ticket. Begin your journey at EYW and touch down at O'Hare International Airport (ORD).

  • Look out for offers from American Airlines. This carrier has direct flights from Key West International Airport to Chicago.

  • EYW is about 3 kilometres from central Key West. If you're catching a cab, ride-sharing or driving from the centre, it'll take 5 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the journey time to be around 40 minutes.

  • Have an early flight from Key West International Airport to Chicago? Avoid rushing to the terminal (and get some extra shut-eye) by choosing one of these hotels close to EYW:

  • When it comes to Key West International Airport's on-time performance, 71.92% of flights complete their journey on time.

  • EYW is located at 3491 South Roosevelt Boulevard.

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

  • The lowest price we've found for a one-way Key West International Airport to Chicago flight is RM358. The cheapest price for a return flight is RM717. Bear in mind fares can change due to availability at the time of booking.

  • To secure cheap flights from EYW to Chicago, reserve your trip one month before your departure.

  • May is the best month for picking up an awesome deal on Key West International Airport to Chicago tickets. If you need to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for each month.

  • There's no need to check back in every day to see if fares have dropped when you create a Price Alert. We'll let you know the moment there's an even better deal on cheap flights from EYW to Chicago.

  • Select your ideal departure and arrival times, airlines and number of stops with our filters. Then, sort the results for your flight from Key West International Airport to Chicago by 'Best,' 'Fastest' or 'Cheapest.'

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago takes around 35 minutes by car. The centre is roughly 40 kilometres away.

  • It typically takes 55 minutes if you're travelling by public transport.

  • Book a hotel close to ORD if you have a late flight from Key West International Airport to Chicago. Pick one of these options and make your first night all about rest:

  • Say yes to new adventures by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's usual tourist stops.

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

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is about 19 kilometres from central Chicago. After your flight from Key West International Airport to Chicago, it'll take you around 20 minutes to reach the heart of the city in a ride-share or cab.

  • If you choose to travel on public transport, you'll get to the city centre in 45 minutes or so.

  • Following your EYW to Chicago flight, unwind at a hotel close to MDW. These are some great accommodation options that'll help you sink into relaxation mode:

  • Forget about inconvenient public transport timetables or waiting forever for a cab. Grab a Chicago Midway International Airport rental car and blaze your own trail. Check out the availability and rates from Dollar, Hertz and Budget.

  • Avoid last-minute price surges. Securing your ride four weeks before your arrival at MDW can get you a lower rate.

  • 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 start exploring right away. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to reach driving.

  • The journey will take you around 4 hours 15 minutes using public transport.

  • Enjoy a more leisurely start to your trip by checking in to a hotel near RFD after your EYW to Chicago flight. Unwind after a day of travel or simply give yourself time to get your bearings in a new destination at:

  • Begin your journey without stressing over how to reach your destination with a Chicago Rockford International Airport rental car. You can book a set of wheels from trusted suppliers here like Budget, Alamo and National.

  • Rental providers sometimes offer deals on early bookings, so reserve your ride from RFD a few weeks in advance of your flight from Key West International Airport to Chicago. Plan ahead and your wallet will thank you.

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

Best time to go to Chicago

  • Before securing your flights from Key West International Airport to Chicago, consider which time of year is best for you. Peak season in Chicago offers a bustling atmosphere and plenty to do, while the low season means you'll get cheaper hotel deals and fewer crowds.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your Key West International Airport to Chicago flight ticket then if that's your definition of good weather.

  • Search for cheap tickets from EYW to Chicago in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

  • Once you've booked your flight from Key West International Airport to Chicago, find a hotel that keeps you close to what you want to see. Make one of these accommodation options your base for exploring Chicago:

  • There are so many things to do and see in this city it can be tricky to work out where to begin. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are popular attractions which should be on any well-planned Chicago itinerary.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered once you've seen Chicago. Around 451 kilometres away to the south-east, its best attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another well-known destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Key West to Chicago

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