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$49+ Cheap flights from Kentucky to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$77
(Cheapflightsfares)

One-way from

$49
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$475

Good round-trip deal

$132 or less

Good one-way deal

$162 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)
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One-way flight from Kentucky to Chicago (CHI)
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Highest demand for flights based on searches. 15% potential increase in price ($51 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Kentucky to Chicago (CHI).
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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 March 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/92:28 pmBNA - ORD
Nonstop1h 57mSpirit Airlines
Mon 5/125:20 pmORD - BNA
Nonstop1h 32mSpirit Airlines
Deal found 3/27$77
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Mon 4/284:48 pmBNA - ORD
Nonstop1h 53mMultiple Airlines
Wed 4/305:45 pmORD - BNA
1 stop5h 58mMultiple Airlines
Deal found 3/27$96
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/94:55 pmBNA - ORD
Nonstop2h 04mFrontier
Mon 5/122:36 pmORD - BNA
Nonstop1h 36mFrontier
Deal found 3/27$101
This Southwest deal was found by Cheapflights users on 3/27. 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 6/29:25 pmBNA - MDW
Nonstop1h 35mSouthwest
Wed 6/48:35 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 3/27$137
This Southwest deal was found by Cheapflights users on 3/27. 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 4/2410:50 amBNA - ORD
Nonstop1h 55mSouthwest
Mon 4/284:00 pmORD - BNA
Nonstop1h 40mSouthwest
Deal found 3/27$137
This United Airlines deal was found by Cheapflights users on 3/26. 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 5/28:00 amBNA - ORD
Nonstop1h 51mUnited Airlines
Tue 5/68:05 pmORD - BNA
Nonstop1h 44mUnited Airlines
Deal found 3/26$141
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Tue 4/224:58 pmBNA - ORD
Nonstop1h 57mAmerican Airlines
Sat 4/2610:02 amORD - BNA
Nonstop1h 34mAmerican Airlines
Deal found 3/27$148
This United Airlines deal was found by Cheapflights users on 3/25. 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.
Wed 4/237:29 amSDF - ORD
Nonstop1h 36mUnited Airlines
Wed 4/308:00 pmORD - SDF
Nonstop1h 30mUnited Airlines
Deal found 3/25$157
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/256:10 amCVG - ORD
1 stop13h 07mFrontier
Mon 4/286:30 amORD - CVG
1 stop9h 14mFrontier
Deal found 3/27$158
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1611:00 amCVG - MDW
1 stop11h 33mFrontier
Mon 4/211:10 pmMDW - CVG
1 stop10h 04mFrontier
Deal found 3/27$159
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1712:58 pmBNA - MDW
1 stop11h 23mFrontier
Sun 4/2012:46 pmMDW - BNA
1 stop21h 17mFrontier
Deal found 3/27$160
This Southwest deal was found by Cheapflights users on 3/27. 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 5/173:45 pmSDF - ORD
1 stop7h 15mSouthwest
Tue 5/207:30 amORD - SDF
1 stop7h 55mSouthwest
Deal found 3/27$162

Cheapflights Fare Finder

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 March 28, 2025.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Fly from

Kentucky

Fly to

Chicago

Route

Depart

Return

Price

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 5/9

2:28 pm-4:25 pm

Nonstop1h 57m

Chicago O'Hare Intl

Mon 5/12

5:20 pm-6:52 pm

Nonstop1h 32m

$77

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Mon 4/28

4:48 pm-6:41 pm

Nonstop1h 53m

Chicago O'Hare Intl

Wed 4/30

5:45 pm-11:43 pm

1 stop5h 58m

$96

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 5/9

4:55 pm-6:59 pm

Nonstop2h 04m

Chicago O'Hare Intl

Mon 5/12

2:36 pm-4:12 pm

Nonstop1h 36m

$101

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Mon 6/2

9:25 pm-11:00 pm

Nonstop1h 35m

Chicago Midway

Wed 6/4

8:35 pm-10:05 pm

Nonstop1h 30m

$137

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Thu 4/24

10:50 am-12:45 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 4/28

4:00 pm-5:40 pm

Nonstop1h 40m

$137

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 5/2

8:00 am-9:51 am

Nonstop1h 51m

Chicago O'Hare Intl

Tue 5/6

8:05 pm-9:49 pm

Nonstop1h 44m

$141

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 4/22

4:58 pm-6:55 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sat 4/26

10:02 am-11:36 am

Nonstop1h 34m

$148

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 4/23

7:29 am-8:05 am

Nonstop1h 36m

Chicago O'Hare Intl

Wed 4/30

8:00 pm-10:30 pm

Nonstop1h 30m

$157

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Fri 4/25

6:10 am-6:17 pm

1 stop13h 07m

Chicago O'Hare Intl

Mon 4/28

6:30 am-4:44 pm

1 stop9h 14m

$158

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 4/16

11:00 am-9:33 pm

1 stop11h 33m

Chicago Midway

Mon 4/21

1:10 pm-12:14 am

1 stop10h 04m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

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.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Chicago

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 $323). 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 March 28, 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 March 28, 2025.

The most flights from USKY to CHI are scheduled on a Friday (34 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 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 March 28, 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
4,274 reviews

Entertainment

7.6

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,274 reviews

Entertainment

7.6

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 United Airlines, which is currently one of the cheapest options available, starting at $49. Southwest flights start at $49 while deals on Allegiant Air start at $49 one-way.

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

    The most popular flight routes from Kentucky to Chicago are Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl, Nashville Intl - Chicago O'Hare Intl and Knoxville McGhee Tyson - 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: GoJet (100%), Royal Jordanian (93%), Copa Airlines( 93%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $1,588 for a flight from Kentucky to Chicago. The cheapest flight overall is $78 while the most popular route, (Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl) is currently priced at $202.

  • 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 $323). 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.
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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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$106Average$280FlexibilityNo cancel feeOn-time69%
ContourCheapest$116Average$142FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$117Average$262FlexibilityNo cancel feeOn-time71%
DeltaCheapest$135Average$357FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$278FlexibilityNo cancel feeOn-time63%
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