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Find cheap flights from Key West to Illinois from $203

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Illinois departing on 7/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 6/5
Wed 6/12

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Best Illinois Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Chicago
Chicago1 stop$313
Peoria
Peoria2 stops$582
St. Louis
St. Louis1 stop$535

Good to know

Low season

January

High season

February

Cheapest flight

$203
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Key West to Chicago O'Hare Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Key West to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Illinois from Key West is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Key West to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Illinois with an airline and back to Key West with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Illinois from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Key West to the following destinations at these prices or less: Chicago $377 one-way - $476 round-trip
  • Morning departure is around 2% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top airline flying from Key West to Illinois

 
Need help choosing which airline to fly with from Key West to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
American AirlinesOverall score based on 14713 reviews
7.6Boarding
6.6Food
7.1Entertainment
7.2Comfort
8.0Crew
Airline reviews

The CX617 from HK to BKK was delayed more than 1.5 hours.

2.0 MediocreAnonymous, May 2024STL - ORD
Read more about American Airlines reviews

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Key West to Illinois

Recent round-trip flight deals

6/7Fri
1 stopDelta
6h 56mEYW-ORD
6/10Mon
1 stopDelta
6h 20mORD-EYW
$313
6/7Fri
1 stopDelta
4h 46mEYW-MDW
6/10Mon
1 stopDelta
6h 20mMDW-EYW
$333
6/7Fri
2 stopsAmerican Airlines
8h 12mEYW-ORD
6/10Mon
1 stopAmerican Airlines
5h 44mORD-EYW
$470
7/20Sat
1 stopUnited Airlines
6h 20mEYW-ORD
7/20Sat
2 stopsUnited Airlines
10h 07mORD-EYW
$517
9/14Sat
2 stopsUnited Airlines
20h 37mEYW-PIA
9/17Tue
2 stopsUnited Airlines
17h 11mPIA-EYW
$582
9/14Sat
1 stopAmerican Airlines
7h 15mEYW-PIA
9/17Tue
2 stopsAmerican Airlines
10h 30mPIA-EYW
$721
7/20Sat
1 stopAmerican Airlines
6h 05mEYW-ORD
7/20Sat
1 stopAmerican Airlines
14h 25mORD-EYW
$756
6/7Fri
1 stopDelta
4h 46mEYW-MDW
6/10Mon
2 stopsDelta
9h 06mMDW-EYW
$765
9/14Sat
1 stopAmerican Airlines
5h 05mEYW-PIA
9/17Tue
1 stopAmerican Airlines
4h 40mPIA-EYW
$775
6/12Wed
1 stopUnited Airlines
8h 55mEYW-ORD
6/19Wed
1 stopUnited Airlines
6h 35mORD-EYW
$1,021

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Recent one-way flight deals

7/29Mon
1 stopUnited Airlines
23h 01mEYW-ORD
$203
9/13Fri
1 stopUnited Airlines
28h 05mEYW-ORD
$225
7/29Mon
2 stops
23h 33mEYW-ORD
$238
9/13Fri
2 stopsUnited Airlines
18h 45mEYW-ORD
$242
7/28Sun
1 stopUnited Airlines
23h 01mEYW-ORD
$248
7/20Sat
1 stopDelta
6h 59mEYW-ORD
$254
7/29Mon
1 stopDelta
4h 41mEYW-MDW
$254
7/27Sat
1 stopAmerican Airlines
6h 21mEYW-ORD
$258
7/29Mon
3 stops
31h 34mEYW-ORD
$272
7/28Sun
2 stopsAllegiant Air
22h 35mEYW-RFD
$309

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Last minute flights from Key West to Illinois

Last minute flight, train and bus deals

5/11Sat
multi-stopDelta
4h 51mEYW-MDW
5/14Tue
multi-stopDelta
5h 58mMDW-EYW
$378
5/11Sat
multi-stopDelta
6h 48mEYW-ORD
5/14Tue
multi-stopDelta
6h 40mORD-EYW
$388
5/9Thu
multi-stopDelta
6h 45mEYW-ORD
5/12Sun
multi-stopDelta
6h 40mORD-EYW
$428
5/9Thu
multi-stopDelta
5h 47mEYW-MDW
5/12Sun
multi-stopDelta
7h 27mMDW-EYW
$428
5/11Sat
multi-stopUnited Airlines
13h 05mEYW-ORD
5/14Tue
multi-stopUnited Airlines
9h 24mORD-EYW
$493
5/11Sat
multi-stopUnited Airlines
13h 05mEYW-ORD
5/14Tue
multi-stopUnited Airlines
8h 25mORD-EYW
$548
5/9Thu
multi-stopUnited Airlines
12h 37mEYW-ORD
5/12Sun
multi-stopUnited Airlines
19h 15mORD-EYW
$612
5/11Sat
multi-stopUnited Airlines
8h 03mEYW-ORD
5/14Tue
multi-stopUnited Airlines
9h 47mORD-EYW
$613
5/9Thu
multi-stopUnited Airlines
11h 12mEYW-ORD
5/12Sun
multi-stopUnited Airlines
9h 25mORD-EYW
$668
5/11Sat
multi-stopDelta
25h 57mEYW-MDW
5/14Tue
multi-stopDelta
7h 27mMDW-EYW
$771

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Key West - Illinois Flights

Departure:

Key West (EYW)United States

Return flight deals:

Illinois - Key West

Cabin classes:

$1,105
$1,198
$714
$278