What is the cheapest airline that flies from Chicago to Lexington Blue Grass?

Allegiant Air, United Airlines, and Delta are the most popular carriers operating from Chicago to Lexington Blue Grass

How many flights depart from Chicago to Lexington on average per week?

186 flights are operational weekly from Chicago to Lexington as of May 2026. The most popular departure day for this route is Wed, with 16% of flights per week taking off on this day.

What airlines fly to Lexington?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Lexington from Chicago according to our data. United Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Lexington. Keep in mind that there are 4 different airlines that fly to Lexington on a routine basis, so you have a few additional options to choose from.

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

As of May 2026, there are 26 flights per day flying from Chicago to Lexington. The most common time of day flights depart is 9:00PM, with 42% of flights taking off in the evening.

When did momondo last update prices for flights from Chicago to Lexington Blue Grass Airport?

Prices for flights from Chicago to Lexington Blue Grass Airport refresh daily.

How many operators does momondo search for flights from Chicago to Lexington Blue Grass Airport?

The number of operators available for flights from Chicago to Lexington Blue Grass Airport is 2 as of May 2026.

How old do you have to be to fly from Chicago to Lexington Blue Grass Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Lexington Blue Grass Airport.

What documentation or ID do you need to fly to Lexington Blue Grass Airport?

The travel and health documents you'll need for your trip to Lexington Blue Grass Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Lexington Blue Grass Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$107 Cheap Flights from Chicago to Lexington in 2026

Q: What is the typical price of a round-trip flight between Chicago and Lexington?

Prices are currently low for flights on this route. Typical prices usually range from $399 to $249. The lowest price recently found on this route was $249.

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Find the cheapest flights from Chicago to Lexington

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One-way

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Cheap round-trip flights

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8:10 am - 10:44 am

ORD

LEX

1h 34mnonstop

6:47 pm - 7:46 pm

LEX

ORD

1h 59mnonstop

$249American Airlines

พฤ., มิ.ย. 4 - ส., มิ.ย. 6

8:06 am - 10:42 am

ORD

LEX

1h 36mnonstop

5:19 am - 5:55 am

LEX

ORD

1h 36mnonstop

$250American Airlines

พฤ., พ.ค. 28 - จ., มิ.ย. 1

8:10 am - 10:44 am

ORD

LEX

1h 34mnonstop

6:36 pm - 7:35 pm

LEX

ORD

1h 59mnonstop

$251American Airlines

พฤ., มิ.ย. 18 - พฤ., มิ.ย. 25

8:10 am - 10:44 am

ORD

LEX

1h 34mnonstop

5:00 am - 9:02 am

LEX

ORD

5h 02m

1 stop

$259American Airlines

พฤ., มิ.ย. 4 - อา., มิ.ย. 7

3:44 pm - 6:19 pm

ORD

LEX

1h 35mnonstop

1:08 pm - 4:43 pm

LEX

ORD

4h 35m

1 stop

$260American Airlines

พฤ., พ.ค. 28 - จ., มิ.ย. 1

3:44 pm - 6:19 pm

ORD

LEX

1h 35mnonstop

5:19 am - 5:55 am

LEX

ORD

1h 36mnonstop

$264American Airlines

พฤ., พ.ค. 21 - อา., พ.ค. 24

10:59 am - 5:13 pm

MDW

LEX

5h 14m

1 stop

8:04 am - 12:42 pm

LEX

MDW

5h 38m

1 stop

$269Delta

พ., พ.ค. 27 - จ., มิ.ย. 1

7:05 am - 12:19 pm

ORD

LEX

4h 14m

1 stop

7:59 pm - 11:59 pm

LEX

ORD

5h 00m

1 stop

$269Delta

ส., มิ.ย. 6 - อา., มิ.ย. 7

7:55 pm - 10:27 pm

ORD

LEX

1h 32mnonstop

5:15 am - 6:05 am

LEX

ORD

1h 50mnonstop

$279United Airlines

อ., พ.ค. 19 - ส., พ.ค. 23

9:14 am - 8:13 am

MDW

LEX

21h 59m

1 stop

11:41 am - 11:07 am

LEX

MDW

24h 26m

2 stops

$333Multiple Airlines

พฤ., ส.ค. 6 - จ., ส.ค. 10

Delta flights from Chicago to Lexington

Our best Delta deals on Chicago to Lexington flight tickets

Delta

May 27

MDW10:59 amChicago Midway

5h 14m

1 stop

LEX5:13 pmLexington Blue Grass

Jun 1

LEX8:04 amLexington Blue Grass

5h 38m

1 stop

MDW12:42 pmChicago Midway

$269

Delta

Sep 4

ORD1:15 pmChicago O'Hare Intl

7h 08m

1 stop

LEX9:23 pmLexington Blue Grass

Sep 6

LEX11:00 amLexington Blue Grass

6h 36m

1 stop

ORD4:36 pmChicago O'Hare Intl

$284

Delta

Jun 13

MDW4:25 pmChicago Midway

6h 39m

1 stop

LEX12:04 amLexington Blue Grass

Jun 14

LEX7:35 amLexington Blue Grass

6h 11m

1 stop

MDW12:46 pmChicago Midway

$289

American Airlines flights from Chicago to Lexington

Our best American Airlines deals on Chicago to Lexington flight tickets

American Airlines

Jun 4

ORD8:10 amChicago O'Hare Intl

1h 34m

LEX10:44 amLexington Blue Grass

Jun 6

LEX6:47 pmLexington Blue Grass

1h 59m

ORD7:46 pmChicago O'Hare Intl

$249

American Airlines

May 28

ORD8:06 amChicago O'Hare Intl

1h 36m

LEX10:42 amLexington Blue Grass

Jun 1

LEX5:19 amLexington Blue Grass

1h 36m

ORD5:55 amChicago O'Hare Intl

$250

American Airlines

Jun 18

ORD8:10 amChicago O'Hare Intl

1h 34m

LEX10:44 amLexington Blue Grass

Jun 25

LEX6:36 pmLexington Blue Grass

1h 59m

ORD7:35 pmChicago O'Hare Intl

$251

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

พฤ. 6/4

8:10 am-10:44 am

Nonstop1h 34m

Lexington Blue Grass

ส. 6/6

6:47 pm-7:46 pm

Nonstop1h 59m

$249

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

พฤ. 5/28

8:06 am-10:42 am

Nonstop1h 36m

Lexington Blue Grass

จ. 6/1

5:19 am-5:55 am

Nonstop1h 36m

$250

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

พฤ. 6/18

8:10 am-10:44 am

Nonstop1h 34m

Lexington Blue Grass

พฤ. 6/25

6:36 pm-7:35 pm

Nonstop1h 59m

$251

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

พฤ. 6/4

8:10 am-10:44 am

Nonstop1h 34m

Lexington Blue Grass

อา. 6/7

5:00 am-9:02 am

1 stop5h 02m

$259

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

พฤ. 5/28

3:44 pm-6:19 pm

Nonstop1h 35m

Lexington Blue Grass

จ. 6/1

1:08 pm-4:43 pm

1 stop4h 35m

$260

Quickest round-trip

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

พฤ. 5/21

3:44 pm-6:19 pm

Nonstop1h 35m

Lexington Blue Grass

อา. 5/24

5:19 am-5:55 am

Nonstop1h 36m

$264

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

พ. 5/27

10:59 am-5:13 pm

1 stop5h 14m

Lexington Blue Grass

จ. 6/1

8:04 am-12:42 pm

1 stop5h 38m

$269

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

ส. 6/6

7:05 am-12:19 pm

1 stop4h 14m

Lexington Blue Grass

อา. 6/7

7:59 pm-11:59 pm

1 stop5h 00m

$269

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

อ. 5/19

7:55 pm-10:27 pm

Nonstop1h 32m

Lexington Blue Grass

ส. 5/23

5:15 am-6:05 am

Nonstop1h 50m

$279

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

พฤ. 8/6

9:14 am-8:13 am

1 stop21h 59m

Lexington Blue Grass

จ. 8/10

11:41 am-11:07 am

2 stops24h 26m

$333

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Lexington

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Chicago and Lexington?

What is the cheapest month to fly to Lexington?

In general, January is the cheapest month to fly from Chicago to Lexington. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $162. If you are unable to visit Lexington during the month of January, then departing from Chicago during the month March is also very affordable. Most momondo users find prices during this month for around $171.

What is the cheapest day to depart on your flight to Lexington?

On average, the least expensive day to fly to Lexington from Chicago is on a Saturday. momondo users have found tickets for Saturday departures for as low as $252. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Monday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $461.

What is the cheapest time of day to depart on your flight to Lexington?

The cheapest time of day to fly to Lexington is in the morning when flights can be purchased for as low as $276. Try not to purchase tickets at noon because they tend to be around $400. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago to Lexington Blue Grass flight route?

Fly from Chicago O'Hare Intl to Lexington Blue Grass for the best Chicago - Lexington Blue Grass flight prices

Can stopping save me money on Chicago to Lexington flights?

No. A direct flight is the cheapest option for a flight between Chicago to Lexington.

How have Chicago to Lexington flight prices changed over time?

As of May 2026, prices for Chicago to Lexington flights are approximately 65% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Lexington

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Lexington according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Lexington (CHI to LEX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Lexington

Best Price Found	$239
Fastest flight time	1h 23m
Direct flights	Every day
Airports in Lexington	1 airport

The best one-way flight to Lexington from Chicago in the past 72 hours is $239. The best round-trip flight deal from Chicago to Lexington found on momondo in the last 72 hours is $269.

The fastest flight from Chicago to Lexington takes 1h 23m

Direct flights go from Chicago to Lexington every day.

There is 1 airport in Lexington. From Chicago there are direct flights to Lexington Blue Grass (LEX).

Search flight deals

Frequently asked questions about flying from Chicago to Lexington

How far is Chicago to Lexington Blue Grass by plane?
Lexington Blue Grass is 312.4 mi away from Chicago. In terms of flight time, this usually takes a little over 1h 23m.
When did momondo last update prices for flights from Chicago to Lexington Blue Grass Airport?
Prices for flights from Chicago to Lexington Blue Grass Airport refresh daily.
How many operators does momondo search for flights from Chicago to Lexington Blue Grass Airport?
The number of operators available for flights from Chicago to Lexington Blue Grass Airport is 2 as of May 2026.
How old do you have to be to fly from Chicago to Lexington Blue Grass Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Lexington Blue Grass Airport.
What documentation or ID do you need to fly to Lexington Blue Grass Airport?
The travel and health documents you'll need for your trip to Lexington Blue Grass Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Lexington Blue Grass Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Lexington?
Based on momondo bookings for flights between Chicago and Lexington, the leading plane model is Canadair (Bombardier) Regional Jet CRJ-550, making up 23.76% of the total bookings. Other popular models include Embraer 170 with 20.87%, Embraer 175 (Enhanced Winglets) with 17.50%, and Embraer 175 with 13.48%.
What is the most popular airline from Chicago to Lexington?
Based on momondo bookings for flights between Chicago and Lexington, the leading airline is American Airlines, making up 51% of the total bookings. Other popular airlines include United Airlines with 49%.

Best airlines flying from Chicago to Lexington

Compare and see reviews for airlines that fly from Chicago to Lexington with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $189	Free Cancellation	Rating 7.1 11,669 reviews		Search American Airlines flights
United Airlines	PriceFrom $189	Free Cancellation	Rating 7.4 9,690 reviews		Search United Airlines flights

United Airlines Flights From Chicago to Lexington
United Airlines operates around 44 flights from Chicago to Lexington every week. The average price of these flights found in the last 72 hours has been $365, but momondo users have found United Airlines deals from Chicago to Lexington from as low as $189 round-trip. United Airlines has been scored 7.4/10 in 9,690 reviews.
American Airlines Flights From Chicago to Lexington
American Airlines (7.1/10 from 11,669 reviews) operates around 24 flights from Chicago to Lexington in any given week. The average American Airlines airfare for this route is around $266, with deals from around $189 rare but found on momondo. Referenced prices are for round-trip Chicago to Lexington flight searches in the last 72 hours.

Richmond

Georgetown

Somerset

Danville

Frankfort

Winchester

Berea

Versailles

Carlisle

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Lexington?

Finding the right flight to Lexington from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Lexington quick and easy, saving you time and money.

Can I find flights from Chicago to Lexington with flexible booking policies on momondo?

All flight searches from Chicago to Lexington on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Lexington?

Once all potential Chicago to Lexington flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Lexington right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Lexington now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Lexington and let you know when they change.

An easier way to manage your Lexington trip

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Cheap flights from Chicago to Lexington from $107

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Lexington departing on 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from Chicago to Lexington

What is the typical price of a round-trip flight between Chicago and Lexington?

What is the cheapest month to fly to Lexington?

What is the cheapest day to depart on your flight to Lexington?

What is the cheapest time of day to depart on your flight to Lexington?

What is the cheapest Chicago to Lexington Blue Grass flight route?

Can stopping save me money on Chicago to Lexington flights?

How have Chicago to Lexington flight prices changed over time?

What is the cheapest airline that flies from Chicago to Lexington Blue Grass?

What airlines fly to Lexington?

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

How many flights depart from Chicago to Lexington on average per week?

When to book flights from Chicago to Lexington

Cheap Chicago to Lexington (CHI to LEX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Lexington

Best Price Found

Fastest flight time

Direct flights

Airports in Lexington

Frequently asked questions about flying from Chicago to Lexington

Best airlines flying from Chicago to Lexington

Compare and see reviews for airlines that fly from Chicago to Lexington with momondo

United Airlines Flights From Chicago to Lexington

American Airlines Flights From Chicago to Lexington

Traveling to a place near Lexington?

Why use momondo?

An easier way to manage your Lexington trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

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List of cabin classes available on flights landing in Lexington. Availability may vary depending on flight origin and airline.

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