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$44+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This Frontier deal was found by Cheapflights users on 11/19. 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.
Mon 12/301:30 pmBNA - ORD
Nonstop1h 53mFrontier
Wed 1/12:45 pmORD - BNA
Nonstop1h 37mFrontier
Deal found 11/19$69
This United Airlines deal was found by Cheapflights users on 11/21. 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 12/136:00 amBNA - ORD
Nonstop1h 53mUnited Airlines
Tue 1/78:05 pmORD - BNA
Nonstop1h 45mUnited Airlines
Deal found 11/21$97
This Southwest deal was found by Cheapflights users on 11/20. 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.
Fri 12/137:35 pmBNA - MDW
Nonstop1h 35mSouthwest
Sat 12/146:00 amMDW - BNA
Nonstop1h 30mSouthwest
Deal found 11/20$98
This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/67:13 pmBNA - MDW
1 stop5h 07mFrontier
Sun 12/87:15 amMDW - BNA
1 stop6h 39mFrontier
Deal found 11/20$125
This Priceline deal was found by Cheapflights users on 11/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/183:57 pmBNA - ORD
1 stop5h 56mMultiple Airlines
Wed 12/252:45 pmORD - BNA
Nonstop1h 37mMultiple Airlines
Deal found 11/20$131
This American Airlines deal was found by Cheapflights users on 11/21. 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.
Sat 12/145:29 amBNA - ORD
Nonstop2h 02mAmerican Airlines
Mon 12/168:45 pmORD - BNA
Nonstop1h 40mAmerican Airlines
Deal found 11/21$132
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Fri 12/137:00 amSDF - ORD
Nonstop1h 41mUnited Airlines
Mon 12/167:50 pmORD - SDF
Nonstop1h 36mUnited Airlines
Deal found 11/20$147
This FlightHub deal was found by Cheapflights users on 11/19. 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.
Fri 12/612:54 pmBNA - ORD
1 stop5h 56mSpirit Airlines
Tue 12/106:37 pmORD - BNA
1 stop24h 23mSpirit Airlines
Deal found 11/19$165
This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/251:50 pmTYS - MDW
Nonstop1h 34mAllegiant Air
Wed 11/276:16 pmMDW - TYS
Nonstop1h 27mAllegiant Air
Deal found 11/21$166
This Frontier deal was found by Cheapflights users on 11/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/66:00 pmCVG - ORD
1 stop7h 45mFrontier
Sun 12/86:10 amORD - CVG
1 stop9h 17mFrontier
Deal found 11/21$168
This United Airlines deal was found by Cheapflights users on 11/21. 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.
Wed 12/187:10 amLEX - ORD
Nonstop1h 42mUnited Airlines
Wed 12/1810:45 amORD - LEX
Nonstop1h 28mUnited Airlines
Deal found 11/21$172
This KAYAK deal was found by Cheapflights users on 11/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1110:50 amSDF - ORD
1 stop6h 40mDelta
Thu 12/127:05 amORD - SDF
1 stop5h 44mDelta
Deal found 11/20$174

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 1/10

2:43 pm-4:36 pm

Nonstop1h 53m

Chicago O'Hare Intl

Sun 1/12

3:09 pm-4:46 pm

Nonstop1h 37m

$58

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 1/11

10:10 am-11:45 am

Nonstop1h 35m

Chicago Midway

Sat 1/11

2:05 pm-3:35 pm

Nonstop1h 30m

$93

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 12/13

6:00 am-7:53 am

Nonstop1h 53m

Chicago O'Hare Intl

Tue 1/7

8:05 pm-9:50 pm

Nonstop1h 45m

$97

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 2/21

11:10 am-1:00 pm

Nonstop1h 50m

Chicago O'Hare Intl

Sun 2/23

7:00 am-8:30 am

Nonstop1h 30m

$98

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 12/6

7:13 pm-12:20 am

1 stop5h 07m

Chicago Midway

Sun 12/8

7:15 am-1:54 pm

1 stop6h 39m

$125

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Sat 12/14

5:29 am-7:31 am

Nonstop2h 02m

Chicago O'Hare Intl

Mon 12/16

8:45 pm-10:25 pm

Nonstop1h 40m

$132

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 12/18

3:57 pm-9:53 pm

1 stop5h 56m

Chicago O'Hare Intl

Wed 12/25

2:45 pm-4:22 pm

Nonstop1h 37m

$135

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 1/9

7:00 am-7:45 am

Nonstop1h 45m

Chicago O'Hare Intl

Mon 1/13

7:59 pm-10:30 pm

Nonstop1h 31m

$147

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 1/18

6:35 am-7:14 am

Nonstop1h 39m

Chicago O'Hare Intl

Mon 1/20

2:55 pm-5:19 pm

Nonstop1h 24m

$157

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Fri 12/6

6:00 pm-12:45 am

1 stop7h 45m

Chicago O'Hare Intl

Sun 12/8

6:10 am-4:27 pm

1 stop9h 17m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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, September is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $232). Flying from Kentucky to Chicago in June is currently the most expensive (average of $308). 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 November 21, 2024.

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 November 21, 2024.

The most flights from USKY to CHI are scheduled on a Wednesday (42 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (27 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 November 21, 2024.
Peruse reviews from past customers who have flown with Frontier, American Airlines and Spirit 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
5,005 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Allegiant Air
7.4
Good
850 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,005 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $44. Southwest flights start at $49 while deals on United Airlines 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 Nashville Intl - Chicago O'Hare Intl, Knoxville McGhee Tyson - Chicago O'Hare Intl and Cincinnati Cinci./N. Kentucky - 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 (95%), Qatar Airways (89%), ANA( 89%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $954 for a flight from Kentucky to Chicago. The cheapest flight overall is $111 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $60.

  • 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, September is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $232). Flying from Kentucky to Chicago in June is currently the most expensive (average of $308). 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

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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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$109Average$260FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$111Average$251FlexibilityNo cancel feeOn-time71%
ContourCheapest$117Average$143FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$135Average$277FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$282FlexibilityNo cancel feeOn-time63%
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