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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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Kentucky to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Kentucky (USKY) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$58
(Frontier)

One-way from

$49
(Frontier)

Good round-trip deal

$123 or less

Good one-way deal

$144 or less
From Kentucky to Chicago (CHI)
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One-way flight from Kentucky to Chicago (CHI)
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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 January 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/212:23 pmBNA - ORD
Nonstop1h 58mFrontier
Mon 2/243:22 pmORD - BNA
Nonstop1h 39mFrontier
Deal found 1/21$57
This Priceline deal was found by Cheapflights users on 1/21. 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.
Tue 3/119:15 pmBNA - ORD
1 stop10h 29mMultiple Airlines
Wed 3/123:22 pmORD - BNA
Nonstop1h 39mMultiple Airlines
Deal found 1/21$98
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/197:20 amBNA - MDW
Nonstop1h 35mSouthwest
Wed 2/268:40 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 1/20$117
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/112:38 pmBNA - ORD
Nonstop1h 54mUnited Airlines
Tue 3/47:43 pmORD - BNA
Nonstop1h 39mUnited Airlines
Deal found 1/20$128
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Wed 2/126:35 amSDF - ORD
Nonstop1h 39mAmerican Airlines
Mon 2/176:30 pmORD - SDF
Nonstop1h 37mAmerican Airlines
Deal found 1/21$137
This Southwest deal was found by Cheapflights users on 1/21. 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 2/138:30 pmBNA - ORD
Nonstop1h 50mSouthwest
Mon 2/177:00 amORD - BNA
Nonstop1h 30mSouthwest
Deal found 1/21$137
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:01 pmBNA - MDW
1 stop6h 16mFrontier
Mon 3/36:40 amMDW - BNA
1 stop6h 43mFrontier
Deal found 1/20$140
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/137:10 amBNA - ORD
Nonstop1h 47mAmerican Airlines
Sat 2/156:40 pmORD - BNA
Nonstop1h 43mAmerican Airlines
Deal found 1/21$148
This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/111:33 pmBNA - ORD
1 stop21h 32mSpirit Airlines
Tue 2/182:29 pmORD - BNA
1 stop7h 26mSpirit Airlines
Deal found 1/20$158
This Southwest deal was found by Cheapflights users on 1/21. 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.
Tue 4/112:55 pmSDF - MDW
Nonstop1h 15mSouthwest
Thu 4/39:50 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 1/21$167
This Booking.com deal was found by Cheapflights users on 1/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/66:00 amCVG - MDW
1 stop19h 17mFrontier
Sun 2/98:45 amMDW - CVG
1 stop12h 34mFrontier
Deal found 1/21$170
This Booking.com deal was found by Cheapflights users on 1/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/66:00 amCVG - ORD
1 stop9h 02mFrontier
Sun 2/97:00 amORD - CVG
1 stop14h 19mFrontier
Deal found 1/21$170

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 2/21

2:23 pm-4:21 pm

Nonstop1h 58m

Chicago O'Hare Intl

Mon 2/24

3:22 pm-5:01 pm

Nonstop1h 39m

$58

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 2/19

6:29 pm-8:27 pm

Nonstop1h 58m

Chicago O'Hare Intl

Tue 2/25

2:29 pm-9:55 pm

1 stop7h 26m

$106

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 2/19

7:20 am-8:55 am

Nonstop1h 35m

Chicago Midway

Wed 2/26

8:40 pm-10:10 pm

Nonstop1h 30m

$117

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Sat 3/1

12:38 pm-2:32 pm

Nonstop1h 54m

Chicago O'Hare Intl

Tue 3/4

7:43 pm-9:22 pm

Nonstop1h 39m

$128

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 2/12

6:35 am-7:14 am

Nonstop1h 39m

Chicago O'Hare Intl

Mon 2/17

6:30 pm-9:07 pm

Nonstop1h 37m

$137

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Thu 2/13

8:30 pm-10:20 pm

Nonstop1h 50m

Chicago O'Hare Intl

Mon 2/17

7:00 am-8:30 am

Nonstop1h 30m

$137

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 2/28

6:01 pm-12:17 am

1 stop6h 16m

Chicago Midway

Mon 3/3

6:40 am-1:23 pm

1 stop6h 43m

$140

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 2/19

5:30 am-7:15 am

Nonstop1h 45m

Chicago O'Hare Intl

Wed 2/26

10:01 am-11:36 am

Nonstop1h 35m

$157

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 2/11

1:33 pm-11:05 am

1 stop21h 32m

Chicago O'Hare Intl

Tue 2/18

2:29 pm-9:55 pm

1 stop7h 26m

$158

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 4/1

12:55 pm-1:10 pm

Nonstop1h 15m

Chicago Midway

Thu 4/3

9:50 pm-12:05 am

Nonstop1h 15m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 $320). 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 January 21, 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 January 21, 2025.

The most flights from USKY to CHI are scheduled on a Monday (34 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (24 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 January 21, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines and American 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
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, which is currently one of the cheapest options available, starting at $49. Southwest flights start at $59 while deals on United Airlines start at $59 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: Envoy Air (97%), Qatar Airways (93%), American Airlines( 83%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $1,171 for a flight from Kentucky to Chicago. The cheapest flight overall is $167 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $93.

  • 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 $320). 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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Sky Harbor Intl to O'Hare Intl flights
San Francisco to Midway flights
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Minneapolis to Midway flights
Miami to O'Hare Intl flights
Reagan-National to Midway flights
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Denver to Midway flights
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Newark to St. Louis flights
Dulles Intl to Midway flights
Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
Nashville to O'Hare Intl flights
Boston to Midway flights
Detroit to O'Hare Intl flights
Portland to O'Hare Intl 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$114Average$253FlexibilityNo cancel feeOn-time71%
ContourCheapest$116Average$143FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$116Average$265FlexibilityNo cancel feeOn-time69%
DeltaCheapest$135Average$326FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$282FlexibilityNo cancel feeOn-time63%
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