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202 € Cheap Flights from Chicago to Key West International

Compare Chicago 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 to Key West International

Looking for a cheap last-minute deal or the best return flight from Chicago to Key West International Airport? If you want to travel next month, return fares start from 202 €. Find the lowest prices on one-way and return tickets right here.
Key West.202 € per passenger.Departing Mon, 24 Aug, returning Mon, 31 Aug.Return flight with Allegiant Air and Breeze Airways.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Mon, 24 Aug, arriving in Key West International.Inbound indirect flight with Breeze Airways, departs from Key West International on Mon, 31 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 202 €, select.
Key West.215 € per passenger.Departing Sat, 24 Oct, returning Thu, 29 Oct.Return flight with Frontier Airlines and Allegiant Air.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Key West International.Inbound indirect flight with Allegiant Air, departs from Key West International on Thu, 29 Oct, arriving in Chicago Rockford.Price includes taxes and charges.From 215 €, select.
Key West.226 € per passenger.Departing Thu, 27 Aug, returning Thu, 3 Sep.Return flight with Frontier Airlines and Allegiant Air.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 27 Aug, arriving in Key West International.Inbound indirect flight with Allegiant Air, departs from Key West International on Thu, 3 Sep, arriving in Chicago Rockford.Price includes taxes and charges.From 226 €, select.
Key West.227 € per passenger.Departing Tue, 1 Sep, returning Thu, 3 Sep.Return flight with Frontier Airlines and Allegiant Air.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 1 Sep, arriving in Key West International.Inbound indirect flight with Allegiant Air, departs from Key West International on Thu, 3 Sep, arriving in Chicago Rockford.Price includes taxes and charges.From 227 €, select.
Key West.252 € per passenger.Departing Sat, 26 Sep, returning Sat, 3 Oct.Return flight with Frontier Airlines and Breeze Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 26 Sep, arriving in Key West International.Inbound indirect flight with Breeze Airways, departs from Key West International on Sat, 3 Oct, arriving in Chicago Rockford.Price includes taxes and charges.From 252 €, select.
Key West.259 € per passenger.Departing Wed, 28 Oct, returning Sun, 1 Nov.Return flight with Allegiant Air and Breeze Airways.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Wed, 28 Oct, arriving in Key West International.Inbound indirect flight with Breeze Airways, departs from Key West International on Sun, 1 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 259 €, select.
Key West.270 € per passenger.Departing Sat, 24 Oct, returning Wed, 28 Oct.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Key West International.Inbound direct flight with United departs from Key West International on Wed, 28 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 270 €, select.
Key West.270 € per passenger.Departing Mon, 11 Jan, returning Fri, 22 Jan.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 11 Jan, arriving in Key West International.Inbound direct flight with United departs from Key West International on Fri, 22 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 270 €, select.
Key West.270 € per passenger.Departing Sun, 30 May, returning Sat, 5 Jun.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 30 May, arriving in Key West International.Inbound direct flight with United departs from Key West International on Sat, 5 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From 270 €, select.
Key West.271 € per passenger.Departing Tue, 8 Dec, returning Tue, 15 Dec.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 8 Dec, arriving in Key West International.Inbound direct flight with United departs from Key West International on Tue, 15 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 271 €, select.
Key West.277 € per passenger.Departing Fri, 31 Jul, returning Thu, 6 Aug.Return flight with Allegiant Air and Breeze Airways.Outbound indirect flight with Allegiant Air, departs from Chicago Midway on Fri, 31 Jul, arriving in Key West International.Inbound indirect flight with Breeze Airways, departs from Key West International on Thu, 6 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 277 €, select.
Key West.287 € per passenger.Departing Wed, 10 Feb, returning Wed, 17 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 10 Feb, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Wed, 17 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From 287 €, select.
Key West.288 € per passenger.Departing Mon, 2 Nov, returning Sat, 7 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 2 Nov, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Sat, 7 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 288 €, select.
Key West.296 € per passenger.Departing Sun, 2 Aug, returning Sat, 8 Aug.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 2 Aug, arriving in Key West International.Inbound direct flight with United departs from Key West International on Sat, 8 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 296 €, select.
Key West.318 € per passenger.Departing Sat, 26 Sep, returning Sat, 3 Oct.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 26 Sep, arriving in Key West International.Inbound direct flight with United departs from Key West International on Sat, 3 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 318 €, select.
Key West.335 € per passenger.Departing Sat, 28 Nov, returning Sat, 5 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 28 Nov, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Sat, 5 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 335 €, select.

Find the cheapest month to fly from Chicago 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 to Key West International flights are currently cheapest in August.
Jul
from 338 €
Aug
from 202 €
Sep
from 227 €
Oct
from 215 €
Nov
from 288 €
Dec
from 271 €
Jan
from 270 €
Feb
from 287 €
Mar
from 504 €
Apr
from 438 €
May
from 497 €
Jun
Find prices

Direct flights from Chicago to Key West International

Chicago to Key West International: Alternative routes

Compare routes from Chicago 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 202 €
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Chicago to Key West: Flight information

The things to know before you go.
Cheapest flight found202 €
Cheapest month to flyAugust
Average flight time3 hrs, 22 mins
Most popular airlineEnvoy Air
Average flights per week50

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

The best price we found for a return flight from Chicago to Key West International is 202 €. 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 22 minutes is the average flight time from Chicago to Key West International.
Envoy Air, American Airlines and United fly direct from Chicago to Key West International.
As of July 2026, there are 50 flights per week flying from Chicago to Key West International.
The cheapest month to fly from Chicago to Key West International is usually August.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Key West International Airport on Monday, 24 August 2026.
Yes – the average flight time is 3 hours and 22 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 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.

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

  • Your next big escape starts at Chicago's main airport, Chicago O'Hare International Airport (ORD). Explore your options for catching a flight from Chicago to Key West International Airport (EYW) departing from this base.

  • Take off on a direct Chicago to Key West International Airport flight and you'll be travelling for around 3 hours 20 minutes.

  • Key West is one hour ahead of Chicago. Key West International Airport is located in Key West, which follows the UTC-5 timezone.

  • With 18 direct weekly flights between the two airports, Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW) is the most popular route. United Airlines operates the earliest flight at 7:10am. If you're eager to make the most of your day before flying, the last flight from ORD to EYW is with United Airlines at 6pm.

  • Arrive at the airport on time so you don't miss your flight from Chicago to EYW. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.

  • With more travellers during busy months like July, get to the terminal earlier than usual. Two hours for domestic flights and up to four for international journeys will help you stay ahead of the crowds. Remember things also get busy during major holidays like Christmas and local events or festivals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) makes it easy to travel directly to your destination. Nonstop flights from Chicago to Key West International Airport (EYW) depart from this terminal.

  • You can travel on a direct flight from Chicago to Key West International Airport with United Airlines. This well-known airline offers services from ORD.

  • The majority of passengers choose to fly with United between ORD and EYW.

  • The most reliable carrier for punctuality on this route is American Airlines. Its services land without delay 75.65% of the time.

  • Located around 27 kilometres from the centre of Chicago, ORD can be reached in about 30 minutes by car, depending on traffic. The journey on public transport is roughly 45 minutes.

  • Want a hassle-free start to your trip? Stay near Chicago O'Hare International Airport. Whether you're boarding an early flight from Chicago to Key West International Airport or prefer not to rush, these hotels are just the thing:

  • When it comes to Chicago O'Hare International Airport's on-time performance, data shows 70% of flights arrive within the scheduled time frame.

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

Chicago Midway International Airport (MDW)

  • You can reach MDW from central Chicago in about 25 minutes by car, depending on traffic conditions. The ride by public transport takes roughly 30 minutes to travel the 16 kilometres or so.

  • Want to enjoy an extra night away before your Chicago to EYW flight? Kick back in a hotel near Chicago Midway International Airport before your trip officially starts. These stays are calling your name:

  • Chicago Midway International Airport has an on-time performance rate of 76%. This figure provides insight into how often flights that leave from this airport make it to their destination on schedule.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From central Chicago, RFD is around 145 kilometres away. It'll take you roughly 1 hour 40 minutes to reach the airport by car and 2 hours or so if you take public transport.

  • Make catching an early Chicago to Key West International Airport flight the easiest part of your journey. Book a room at one of these accommodation options near Chicago Rockford International Airport and get to your departure gate with plenty of time to spare:

  • The on-time performance record of RFD is 71%. In other words, that's how often flights departing this airport arrive within the expected time frame.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Key West International Airport (EYW)

  • If you're coming in on a late flight from Chicago to Key West International Airport, nothing tops the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and resting soon after at one of these hotels near EYW:

  • Booking your vehicle around two weeks in advance of your Chicago to Key West International Airport flight can help you secure the lowest rate.

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

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

  • From Key West International Airport, central Key West is around 5 kilometres away. It takes about 10 minutes to reach the city centre by car.

  • Travelling on public transport takes around 20 minutes.

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

  • At the moment, 104 € is the best price we've found for a one-way ticket from Chicago to Key West International Airport. The cheapest price for a return flight is 202 €. Keep in mind fares may change due to demand at the time of booking.

  • To snap up cheap flights from Chicago to EYW, book your plane ticket two months before your departure date.

  • July is when you're most likely to land a good deal on a Chicago to Key West International Airport ticket. If you want to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for every month.

  • You don't need to check every day to find out if fares have dropped when you create a Price Alert. We'll notify you as soon as there's a better deal on plane tickets from Chicago to EYW.

  • Lock in a cheap flight from Chicago to Key West International Airport by using filters. Choose your ideal times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Chicago to Key West International Airport (EYW)

  • It's time to work out when to book your flight from Chicago to Key West International Airport (EYW). March is when most people visit Key West. If you prefer a quieter vibe, head there in September.

  • The warmest month in Key West is August, with temperatures ranging between 26ºC (79ºF) and 30ºC (86ºF). Book your Chicago to EYW plane ticket then if that's your idea of comfortable weather.

  • January has temperatures of between 18ºC (64ºF) and 23ºC (73ºF). Search for cheap tickets from Chicago to Key West International Airport around that time if you want to travel when it's cooler.

More about Key West

  • Once you've booked your flight from Chicago to Key West International Airport, find a hotel that offers the right mix of comfort and location. Make one of these options your base for exploring Key West:

  • There are plenty of things to do in Key West when you're ready to sightsee. Kick things off at South Beach followed by Mallory Square and Dry Tortugas.

Explore more of the United States

  • Key West has its own special appeal, but there are so many other corners of the United States waiting to be explored. Around 209 kilometres northeast of Key West, a trip to Miami will keep you busy. Start with leading sights like Beach, Ocean Drive and Port of Miami.

  • Hialeah is another essential stop in the United States and is around 209 kilometres northeast of Key West. No journey is complete without visiting Amelia Earhart Park, Hialeah Park and Assault Brigde 2506 Museum.

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