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$43+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Nov 9 — Nov 161
1 adult
Sat 11/9
Sat 11/16
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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 November 4, 2024.

This Gotogate deal was found by Cheapflights users on 11/3. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/166:27 pmBNA - ORD
Nonstop1h 51mFrontier
Mon 11/1812:57 pmORD - BNA
Nonstop1h 36mFrontier
Deal found 11/3$65
This FareScan deal was found by Cheapflights users on 11/3. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/39:09 pmBNA - ORD
1 stop27h 25mSpirit Airlines
Tue 12/106:37 pmORD - BNA
1 stop24h 23mSpirit Airlines
Deal found 11/3$117
This Frontier deal was found by Cheapflights users on 11/3. 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 12/67:13 pmBNA - MDW
1 stop5h 07mFrontier
Mon 12/97:15 amMDW - BNA
1 stop10h 08mFrontier
Deal found 11/3$118
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Wed 12/181:30 pmBNA - ORD
Nonstop1h 53mMultiple Airlines
Wed 12/251:24 pmORD - BNA
1 stop11h 10mMultiple Airlines
Deal found 11/4$120
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/115:30 amBNA - ORD
Nonstop1h 54mAmerican Airlines
Sun 12/158:23 amORD - BNA
Nonstop1h 44mAmerican Airlines
Deal found 11/3$137
This Southwest deal was found by Cheapflights users on 11/4. 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 12/145:45 amBNA - MDW
Nonstop1h 35mSouthwest
Sun 12/1510:25 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 11/4$138
This United Airlines deal was found by Cheapflights users on 11/4. 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 12/77:00 amTYS - ORD
Nonstop2h 01mUnited Airlines
Mon 12/95:50 pmORD - TYS
Nonstop1h 45mUnited Airlines
Deal found 11/4$159
This Southwest deal was found by Cheapflights users on 11/3. 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 12/411:15 amBNA - ORD
Nonstop1h 45mSouthwest
Thu 12/51:45 pmORD - BNA
1 stop6h 20mSouthwest
Deal found 11/3$167
This Frontier deal was found by Cheapflights users on 11/3. 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 11/226:00 amCVG - MDW
1 stop6h 10mFrontier
Sun 11/2412:39 pmMDW - CVG
1 stop10h 41mFrontier
Deal found 11/3$168
This Frontier deal was found by Cheapflights users on 11/3. 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 11/226:20 amCVG - ORD
1 stop6h 55mFrontier
Sun 11/245:15 amORD - CVG
1 stop10h 23mFrontier
Deal found 11/3$168
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/46:30 amBNA - MDW
1 stop6h 19mDelta
Mon 12/99:30 amMDW - BNA
1 stop3h 52mDelta
Deal found 11/3$176
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/137:19 pmBNA - ORD
1 stop4h 39mDelta
Sun 12/155:40 amORD - BNA
1 stop6h 04mDelta
Deal found 11/4$176

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 2,455,398 searches. Data last updated November 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 11/22

1:50 pm-2:24 pm

Nonstop1h 34m

$48

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 12/25

1:30 pm-3:23 pm

Nonstop1h 53m

$49

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 12/3

9:09 pm-12:34 am

1 stop27h 25m

$52

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 12/3

10:35 am-12:15 pm

Nonstop1h 40m

$59

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Sat 2/1

6:00 am-8:05 am

Nonstop2h 05m

$70

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 12/3

6:30 am-12:49 pm

1 stop6h 19m

$88

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Tue 12/24

6:00 am-4:06 pm

1 stop11h 06m

$102

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 11/19

11:16 am-1:04 pm

Nonstop1h 48m

$105

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 1/30

6:40 am-2:45 pm

1 stop9h 05m

$53

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 12/5

7:00 am-3:12 pm

1 stop9h 12m

$54

Flights are sorted by cheapest first

Deals found on 11/3

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 4, 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 4, 2024.

The most flights from USKY to CHI are scheduled on a Monday (41 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 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 4, 2024.
Peruse reviews from past customers who have flown with American Airlines, United Airlines and Delta 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
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

United Airlines
7.4
Good
9,226 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

WestJet
7.3
Good
2,803 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

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.

  • Can I find flights from Kentucky to Chicago for under $100 on Cheapflights?

    Yes, there are multiple flights from Kentucky to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $57, but on average you can expect to pay $155.

  • Are there nonstop flights from Kentucky to Chicago for under $100 on Cheapflights?

    Cheapflights has at least 16 direct flights from Kentucky to Chicago under $100. A good price for a nonstop flight from Kentucky to Chicago is less than $215.

  • Are there last-minute flights available from Kentucky to Chicago for under $100?

    There are currently 20+ open flights from Kentucky to Chicago within the next 7 days for less than $100.

  • What days are nonstop flights available from Kentucky to Chicago?

    You can find nonstop flights on the following days: Monday, Tuesday.

  • How many flights depart from Kentucky to Chicago on average per day?

    23 flight departures from Kentucky to Chicago per day on average.
    Morning (6am - Noon) - 22% of flight departures
    Afternoon (Noon - 6pm) - 78% of flight departures

  • How long is the flight from Kentucky to Chicago?

    There are many flights that can get you from Kentucky to Chicago in 1h 47m. Fly via Frontier, Spirit Airlines, or American Airlines to get the fastest option. The distance from Kentucky to Chicago is about 288 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $43. Allegiant Air flights start at $48 while deals on Spirit Airlines start at $52 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: SkyWest Airlines (94%), Copa Airlines (92%), ANA( 90%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $920 for a flight from Kentucky to Chicago. The cheapest flight overall is $88 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $71.

  • What does SDF to ORD mean?

    Louisville Intl Airport is SDF and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Kentucky to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Kentucky to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Kentucky to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Kentucky to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Kentucky to Chicago that allow pets onboard?

    Many airlines flying from Kentucky to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Kentucky to Chicago?

    Yes, you can often find last-minute deals on Kentucky to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Kentucky to Chicago flight deals updated?

    The Kentucky to Chicago flight deals you see on this page were last updated on 11/4.

  • 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 2,455,398 searches. Data last updated November 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$108Average$245FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$117Average$253FlexibilityNo cancel feeOn-time71%
ContourCheapest$117Average$142FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$135Average$286FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$268FlexibilityNo cancel feeOn-time63%
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