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$38+ Cheap flights from Kentucky to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
1 adult, Economy
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Cheap flight deals from Kentucky to Chicago

Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$38
(Frontier)

Popular in

March

Cheapest in

August

Average price

$258

Good round-trip deal

$121 or less

Good one-way deal

$186 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
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From Kentucky to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Kentucky to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Kentucky to Chicago (CHI).
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Find flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/72:03 pmBNA - ORD
Nonstop1h 58mFrontier
Mon 3/103:22 pmORD - BNA
Nonstop1h 39mFrontier
Deal found 2/22$52
This Priceline deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/199:50 pmBNA - ORD
1 stop9h 44mMultiple Airlines
Wed 3/263:22 pmORD - BNA
Nonstop1h 39mMultiple Airlines
Deal found 2/21$57
This Mytrip deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/29:23 amBNA - MDW
1 stop24h 01mFrontier
Wed 4/96:45 amMDW - BNA
1 stop6h 27mFrontier
Deal found 2/21$110
This FlightHub deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/199:50 pmBNA - ORD
1 stop9h 44mSpirit Airlines
Wed 3/2610:40 amORD - BNA
1 stop9h 23mSpirit Airlines
Deal found 2/21$114
This American Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/248:56 amSDF - ORD
Nonstop1h 38mAmerican Airlines
Mon 4/288:25 pmORD - SDF
Nonstop1h 35mAmerican Airlines
Deal found 2/21$117
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/136:50 amSDF - MDW
Nonstop1h 15mSouthwest
Mon 3/179:50 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 2/21$117
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/245:10 amBNA - MDW
Nonstop1h 40mSouthwest
Mon 3/319:45 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 2/22$117
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2210:50 amBNA - ORD
Nonstop1h 55mSouthwest
Wed 4/234:00 pmORD - BNA
Nonstop1h 40mSouthwest
Deal found 2/22$117
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/47:05 amBNA - ORD
Nonstop1h 53mAmerican Airlines
Tue 4/88:20 pmORD - BNA
Nonstop1h 49mAmerican Airlines
Deal found 2/20$131
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/77:02 amSDF - ORD
Nonstop1h 48mUnited Airlines
Wed 4/96:01 pmORD - SDF
Nonstop1h 28mUnited Airlines
Deal found 2/21$133
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/136:05 amSDF - ORD
1 stop8h 00mSouthwest
Tue 3/187:30 amORD - SDF
1 stop6h 20mSouthwest
Deal found 2/21$142
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/81:05 pmCVG - MDW
Nonstop1h 10mSouthwest
Mon 3/104:45 pmMDW - CVG
1 stop6h 30mSouthwest
Deal found 2/21$142

Find flights from Kentucky to Chicago within your budget

Customize your flight search to find flights from Kentucky to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 22, 2025.

Fly from

Kentucky

Fly to

Chicago

Route

Depart

Return

Price

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 3/7

2:03 pm-4:01 pm

Nonstop1h 58m

Chicago O'Hare Intl

Mon 3/10

3:22 pm-5:01 pm

Nonstop1h 39m

$52

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 3/19

9:50 pm-7:34 am

1 stop9h 44m

Chicago O'Hare Intl

Wed 3/26

3:22 pm-5:01 pm

Nonstop1h 39m

$57

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 4/2

9:23 am-9:24 am

1 stop24h 01m

Chicago Midway

Wed 4/9

6:45 am-1:12 pm

1 stop6h 27m

$110

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 4/2

9:50 pm-7:34 am

1 stop9h 44m

Chicago O'Hare Intl

Wed 4/9

6:30 am-4:05 pm

1 stop9h 35m

$113

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 4/24

8:56 am-9:34 am

Nonstop1h 38m

Chicago O'Hare Intl

Mon 4/28

8:25 pm-11:00 pm

Nonstop1h 35m

$117

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 3/13

6:50 am-7:05 am

Nonstop1h 15m

Chicago Midway

Mon 3/17

9:50 pm-12:05 am

Nonstop1h 15m

$117

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Mon 3/24

5:10 am-6:50 am

Nonstop1h 40m

Chicago Midway

Mon 3/31

9:45 pm-11:15 pm

Nonstop1h 30m

$117

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 4/22

10:50 am-12:45 pm

Nonstop1h 55m

Chicago O'Hare Intl

Wed 4/23

4:00 pm-5:40 pm

Nonstop1h 40m

$117

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 4/4

7:05 am-8:58 am

Nonstop1h 53m

Chicago O'Hare Intl

Tue 4/8

8:20 pm-10:09 pm

Nonstop1h 49m

$131

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Fri 3/7

7:02 am-7:50 am

Nonstop1h 48m

Chicago O'Hare Intl

Wed 4/9

6:01 pm-8:29 pm

Nonstop1h 28m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Kentucky to Chicago

Get recent, data-driven insights about flights from Kentucky to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Kentucky to Chicago?

Currently, August is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $245). Flying from Kentucky to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from KY to CHI?

Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 22, 2025.

When flying from Kentucky to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Kentucky to Chicago

Explore weekly flight availability from Kentucky to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 22, 2025.

The most flights from USKY to CHI are scheduled on a Thursday (34 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (18 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 22, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Kentucky to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
764 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Kentucky to Chicago one-way?

    To fly one-way, consider booking your trip with Allegiant Air, which is currently one of the cheapest options available, starting at $54. Frontier flights start at $55 while deals on Spirit Airlines start at $58 one-way.

  • What are the most popular routes from Kentucky to Chicago?

    The most popular flight routes from Kentucky to Chicago are Nashville Intl - Chicago O'Hare Intl, Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl and Louisville Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Kentucky to Chicago?

    Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Royal Jordanian (85%), Copa Airlines (85%), Japan Airlines( 84%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $1,034 for a flight from Kentucky to Chicago. The cheapest flight overall is $113 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $75.

  • Can I find deals for flights from Kentucky to Chicago that include hotel bookings?

    Yes. In addition to deals on Kentucky to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kentucky to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Chicago.

  • Can I find deals for business class flights from Kentucky to Chicago?

    Yes. Cheapflights offers flight deals from Kentucky to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kentucky to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $245). Flying from Kentucky to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Kentucky?

Book flights to Kentucky if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Kentucky to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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Los Angeles to Midway flights
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LaGuardia to Midway flights
Austin to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Seattle to Midway flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Dallas/Fort Worth to Midway flights
Hobby to Midway flights
Tampa to O'Hare Intl flights
San Francisco to Midway flights
Newark to St. Louis flights
Miami to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Portland to O'Hare Intl flights
Minneapolis to Midway flights
LaGuardia to St. Louis flights
Baltimore to Midway flights
Boston to Midway flights
Cleveland to O'Hare Intl flights
Detroit to O'Hare Intl flights
Reagan-National to Midway flights

Top 5 airlines flying from Kentucky to Chicago

Discover the top 5 airlines that operate flights from Kentucky to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$113Average$274FlexibilityNo cancel feeOn-time69%
ContourCheapest$113Average$143FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$117Average$257FlexibilityNo cancel feeOn-time71%
DeltaCheapest$135Average$357FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$178Average$277FlexibilityNo cancel feeOn-time63%
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