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$40 Find Cheap Flights from Kentucky to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 1/17. 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

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In the last 7 days travelers have searched 46,479,581 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

October

Cheapest flight

$40
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Nashville to Chicago O'Hare Airport

FAQs for booking flights from Kentucky to Chicago

  • How does KAYAK find such low prices on flights from Kentucky to Chicago?

    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 Kentucky to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Kentucky 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 Kentucky to Chicago?

    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 Chicago with an airline and back to Kentucky with another airline.

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

    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 Chicago from Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Kentucky to Chicago?

Find which airlines fly direct from Kentucky to Chicago, which days they fly and book direct flights.

Nonstop departures

Kentucky to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Kentucky

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Book cheap flights from Kentucky to Chicago

Recent round-trip flight deals

11/15Fri
nonstopFrontier
1h 51mBNA-ORD
11/17Sun
nonstopFrontier
1h 36mORD-BNA
$60
11/9Sat
nonstopFrontier
1h 51mBNA-ORD
11/25Mon
nonstopFrontier
1h 36mORD-BNA
$63
11/22Fri
nonstopAllegiant Air
1h 34mTYS-MDW
11/25Mon
nonstopAllegiant Air
1h 27mMDW-TYS
$94
11/15Fri
nonstopAllegiant Air
1h 34mTYS-MDW
11/18Mon
nonstopAllegiant Air
1h 27mMDW-TYS
$95
12/3Tue
nonstopAmerican Airlines
1h 54mBNA-ORD
12/10Tue
nonstopAmerican Airlines
1h 40mORD-BNA
$99
12/3Tue
nonstopAmerican Airlines
1h 54mBNA-ORD
12/11Wed
nonstopAmerican Airlines
1h 40mORD-BNA
$100
12/13Fri
nonstopSouthwest
1h 35mBNA-MDW
12/16Mon
nonstopSouthwest
1h 30mMDW-BNA
$100
11/5Tue
1 stop
13h 55mBNA-ORD
11/17Sun
nonstop
1h 36mORD-BNA
$113
11/15Fri
nonstop
1h 34mTYS-MDW
11/18Mon
1 stop
14h 30mMDW-TYS
$115
12/13Fri
1 stopSouthwest
4h 40mBNA-MDW
12/15Sun
nonstopSouthwest
1h 35mMDW-BNA
$138

Search by stops

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Recent one-way flight deals

1/17Fri
nonstopFrontier
1h 47mBNA-ORD
$40
1/1Wed
nonstopFrontier
1h 53mBNA-ORD
$41
12/3Tue
1 stopSpirit Airlines
13h 08mBNA-ORD
$49
12/8Sun
nonstopSouthwest
1h 35mBNA-MDW
$50
12/16Mon
nonstopUnited Airlines
1h 53mBNA-ORD
$50
11/8Fri
nonstopAllegiant Air
1h 33mTYS-MDW
$51
1/7Tue
nonstopSouthwest
1h 35mBNA-MDW
$59
1/8Wed
nonstopUnited Airlines
2h 05mBNA-ORD
$59
11/15Fri
nonstopAllegiant Air
1h 34mTYS-MDW
$60
11/13Wed
2 stopsSpirit Airlines
15h 00mBNA-ORD
$75

Search by stops

Search by airline

Search by price

Last minute flights from Kentucky to Chicago

Last minute flight, train and bus deals

11/5Tue
multi-stop
13h 55mBNA-ORD
11/17Sun
nonstop
1h 36mORD-BNA
$113
11/2Sat
nonstopFrontier
1h 46mBNA-ORD
11/9Sat
nonstopFrontier
1h 41mORD-BNA
$145
11/4Mon
multi-stopSpirit Airlines
11h 43mBNA-ORD
11/5Tue
multi-stopSpirit Airlines
15h 51mORD-BNA
$252
11/5Tue
multi-stopSpirit Airlines
26h 00mBNA-ORD
11/17Sun
multi-stopSpirit Airlines
15h 53mORD-BNA
$257
11/2Sat
nonstopUnited Airlines
1h 36mCVG-ORD
11/2Sat
multi-stopUnited Airlines
16h 29mORD-CVG
$318
11/2Sat
multi-stopUnited Airlines
19h 27mSDF-ORD
11/3Sun
nonstopUnited Airlines
1h 33mORD-SDF
$348
11/1Fri
nonstopAmerican Airlines
1h 56mTYS-ORD
11/4Mon
nonstopAmerican Airlines
1h 45mORD-TYS
$349
11/1Fri
multi-stopAmerican Airlines
5h 41mTYS-ORD
11/2Sat
nonstopAmerican Airlines
1h 39mORD-TYS
$359
11/1Fri
multi-stopDelta
6h 59mTYS-ORD
11/2Sat
multi-stopDelta
4h 14mORD-TYS
$368
11/1Fri
multi-stopDelta
6h 22mSDF-ORD
12/4Wed
multi-stopDelta
4h 51mORD-SDF
$444

Search by stops

Search by airline

Search by price

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Kentucky

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.