Cheap flights from Key West International to Chicago

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Compare Key West International to Chicago flight deals

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Flight deals from Key West International to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Key West International Airport to Chicago? If you want to travel next month, round-trip fares start from $257. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$254 per passenger.Departing Thu, Oct 29, returning Sun, Nov 1.Round-trip flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departing from Key West International on Thu, Oct 29, arriving in Chicago Rockford.Inbound indirect flight with Allegiant Air, departing from Chicago Rockford on Sun, Nov 1, arriving in Key West International.Price includes taxes and charges.From $254, select.

Chicago.$257 per passenger.Departing Sat, Oct 17, returning Sat, Oct 31.Round-trip flight with Allegiant Air and Frontier Airlines.Outbound indirect flight with Allegiant Air, departing from Key West International on Sat, Oct 17, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Sat, Oct 31, arriving in Key West International.Price includes taxes and charges.From $257, select.

Chicago.$276 per passenger.Departing Thu, Dec 3, returning Sun, Dec 6.Round-trip flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departing from Key West International on Thu, Dec 3, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Sun, Dec 6, arriving in Key West International.Price includes taxes and charges.From $276, select.

Chicago.$277 per passenger.Departing Wed, Sep 30, returning Sun, Oct 4.Round-trip flight with Breeze Airways and Allegiant Air.Outbound indirect flight with Breeze Airways, departing from Key West International on Wed, Sep 30, arriving in Chicago Rockford.Inbound indirect flight with Allegiant Air, departing from Chicago Rockford on Sun, Oct 4, arriving in Key West International.Price includes taxes and charges.From $277, select.

Chicago.$321 per passenger.Departing Thu, Nov 26, returning Mon, Nov 30.Round-trip flight with Allegiant Air and Frontier Airlines.Outbound indirect flight with Allegiant Air, departing from Key West International on Thu, Nov 26, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Mon, Nov 30, arriving in Key West International.Price includes taxes and charges.From $321, select.

Chicago.$334 per passenger.Departing Fri, Jun 11, returning Fri, Jun 25.Round-trip flight with United.Outbound direct flight with United departing from Key West International on Fri, Jun 11, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Jun 25, arriving in Key West International.Price includes taxes and charges.From $334, select.

Chicago.$335 per passenger.Departing Thu, Dec 3, returning Sun, Dec 6.Round-trip flight with United.Outbound direct flight with United departing from Key West International on Thu, Dec 3, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sun, Dec 6, arriving in Key West International.Price includes taxes and charges.From $335, select.

Chicago.$340 per passenger.Departing Fri, Jan 8, returning Fri, Jan 22.Round-trip flight with United.Outbound direct flight with United departing from Key West International on Fri, Jan 8, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Jan 22, arriving in Key West International.Price includes taxes and charges.From $340, select.

Chicago.$344 per passenger.Departing Fri, Apr 9, returning Fri, Apr 23.Round-trip flight with United.Outbound indirect flight with United, departing from Key West International on Fri, Apr 9, arriving in Chicago O'Hare International.Inbound indirect flight with United, departing from Chicago O'Hare International on Fri, Apr 23, arriving in Key West International.Price includes taxes and charges.From $344, select.

Chicago.$383 per passenger.Departing Fri, Feb 12, returning Fri, Feb 26.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Key West International on Fri, Feb 12, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Fri, Feb 26, arriving in Key West International.Price includes taxes and charges.From $383, select.

Chicago.$395 per passenger.Departing Fri, Feb 12, returning Fri, Feb 26.Round-trip flight with United.Outbound direct flight with United departing from Key West International on Fri, Feb 12, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Feb 26, arriving in Key West International.Price includes taxes and charges.From $395, select.

Chicago.$411 per passenger.Departing Fri, May 14, returning Fri, May 28.Round-trip flight with United.Outbound direct flight with United departing from Key West International on Fri, May 14, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, May 28, arriving in Key West International.Price includes taxes and charges.From $411, select.

Chicago.$438 per passenger.Departing Wed, Mar 17, returning Wed, Mar 24.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Key West International on Wed, Mar 17, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Wed, Mar 24, arriving in Key West International.Price includes taxes and charges.From $438, select.

Chicago.$465 per passenger.Departing Wed, Mar 17, returning Wed, Mar 24.Round-trip flight with United.Outbound direct flight with United departing from Key West International on Wed, Mar 17, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Wed, Mar 24, arriving in Key West International.Price includes taxes and charges.From $465, select.

Chicago.$682 per passenger.Departing Mon, Mar 29, returning Mon, Apr 12.Round-trip flight with United.Outbound direct flight with United departing from Key West International on Mon, Mar 29, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Mon, Apr 12, arriving in Key West International.Price includes taxes and charges.From $682, 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 October.

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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.

Key West to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$254
Cheapest month to fly	October
Average flight time	3 hrs, 49 mins
Most popular airline	Envoy Air
Average flights per week	54

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

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are round-trip flights from Key West International to Chicago?

The best price we found for a round-trip flight from Key West International to Chicago is $254. 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.

How long does it take to fly from Key West International to Chicago?

3 hours and 49 minutes is the average flight time from Key West International to Chicago.

Which airlines fly direct from Key West International to Chicago?

Envoy Air, American Airlines and United fly direct from Key West International to Chicago.

How many flights are there a week from Key West International to Chicago?

There are 54 flights per week flying from Key West International to Chicago, as of September 2026.

When is the cheapest time to fly from Key West International to Chicago?

The cheapest month to fly from Key West International to Chicago is usually October.

What's the cheapest airport to fly to in Chicago?

If you're flying from Key West International Airport, the cheapest airport near Chicago is Chicago Rockford – which is 126.5 km away from the center of Chicago. We've found flights to this airport from $254.

Which upcoming date is cheapest to fly from Key West International Airport to Chicago on?

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 Thursday, October 29, 2026.

Can I get a direct flight from Key West International Airport to Chicago?

Yes – the average flight time is 3 hours and 49 minutes.

How can I get the best flight deal from Key West International Airport to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In September, the average temperature is usually around 20°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.

Which is the cheapest airline to fly with from Key West International Airport to Chicago?

Currently, Allegiant Air and United offer the cheapest flight tickets to Chicago.

Traveling 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.
Traveling from central Key West to EYW takes around 20 minutes by public transport. If you drive, ride-share or take a cab, you'll cover the 3 kilometers 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 $100. The cheapest price for a return flight is $254. 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 kilometers. It takes about 30 minutes to reach the center driving.
If you're traveling 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 kilometers 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.
Traveling 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 cozy 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 center of Chicago is around 145 kilometers 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 (61ºF) to 28ºC (82ºF).
Look for cheap tickets from EYW to Chicago in January if you like traveling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

When it comes to looking for somewhere to rest your head, you'll find the best places to stay in Chicago right here. Browse these hotels once you've booked your flight from Key West International Airport to Chicago:
Every great adventure has to include a little sightseeing. Art Institute of Chicago, Millennium Park and Willis Tower are attractions you won't want to skip in 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 kilometers away to the southeast, check out popular attractions including Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theater.
Indianapolis is another well-known destination in the United States and is around 257 kilometers southeast of Chicago. No journey is complete without visiting Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.