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 58% 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.

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?

99 flights are operational weekly from Chicago to Lexington as of August 2026. The most popular departure day for this route is Mon, with 26% of flights per week taking off on this day.

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

As of August 2026, there are 14 flights per day flying from Chicago to Lexington. The most common time of day flights depart is 5:00PM, with 51% of flights taking off in the afternoon.

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 August 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.

$122 Cheap Flights from Chicago to Lexington in 2026

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Find the cheapest flights from Chicago to Lexington

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Cheap round-trip flights

Enter your travel dates to find the best prices.

10:36 am - 1:16 pm-

1h 40mnonstop

1:51 pm - 2:35 pm-

1h 44mnonstop

$259United Airlines

Thu, Aug 27 - Thu, Sep 3

2:59 pm - 5:35 pm-

1h 36mnonstop

1:58 pm - 2:42 pm-

1h 44mnonstop

$259United Airlines

Sat, Aug 29 - Tue, Sep 1

2:57 pm - 5:31 pm-

1h 34mnonstop

5:23 am - 6:10 am-

1h 47mnonstop

$259American Airlines

Fri, Sep 25 - Mon, Sep 28

3:54 pm - 6:25 pm-

1h 31mnonstop

6:59 pm - 7:59 pm-

2h 00mnonstop

$259American Airlines

Fri, Aug 28 - Fri, Sep 4

3:00 pm - 5:36 pm-

1h 36mnonstop

7:00 am - 7:45 am-

1h 45mnonstop

$259United Airlines

Wed, Aug 26 - Sun, Aug 30

8:15 am - 10:56 am-

1h 41mnonstop

11:26 am - 12:14 pm-

1h 48mnonstop

$259American Airlines

Fri, Nov 6 - Sun, Nov 8

5:50 pm - 8:28 pm-

1h 38mnonstop

9:52 am - 10:40 am-

1h 48mnonstop

$259United Airlines

Wed, Aug 26 - Sat, Aug 29

7:11 am - 5:50 pm-

9h 39m

6:40 pm - 2:45 pm-

21h 05m

$278Multiple Airlines

Thu, Sep 17 - Thu, Sep 24

11:22 am - 5:21 pm-

4h 59m

7:35 am - 10:42 am-

4h 07m

$279Delta

Sat, Aug 22 - Sun, Aug 23

6:40 am - 12:11 pm-

4h 31m

10:52 am - 4:17 pm-

6h 25m

$279Delta

Fri, Aug 28 - Fri, Sep 4

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Delta flights from Chicago to Lexington

Our best Delta deals on Chicago to Lexington flight tickets

Delta

Aug 27

MDW6:05 amChicago Midway

5h 06m

1 stop

LEX12:11 pmLexington Blue Grass

Aug 30

LEX7:35 amLexington Blue Grass

6h 04m

1 stop

MDW12:39 pmChicago Midway

$279

Delta

Aug 29

MDW6:11 amChicago Midway

5h 00m

1 stop

LEX12:11 pmLexington Blue Grass

Sep 1

LEX10:10 amLexington Blue Grass

6h 34m

1 stop

MDW3:44 pmChicago Midway

$294

Delta

Sep 8

MDW6:05 amChicago Midway

4h 39m

1 stop

LEX11:44 amLexington Blue Grass

Sep 15

LEX12:40 pmLexington Blue Grass

4h 35m

1 stop

MDW4:15 pmChicago Midway

$299

American Airlines flights from Chicago to Lexington

Our best American Airlines deals on Chicago to Lexington flight tickets

American Airlines

Nov 6

ORD8:15 amChicago O'Hare Intl

1h 41m

LEX10:56 amLexington Blue Grass

Nov 8

LEX11:26 amLexington Blue Grass

1h 48m

ORD12:14 pmChicago O'Hare Intl

$259

American Airlines

Sep 13

ORD9:15 pmChicago O'Hare Intl

1h 31m

LEX11:46 pmLexington Blue Grass

Sep 20

LEX6:01 pmLexington Blue Grass

1h 58m

ORD6:59 pmChicago O'Hare Intl

$260

American Airlines

Aug 27

ORD3:54 pmChicago O'Hare Intl

1h 31m

LEX6:25 pmLexington Blue Grass

Aug 30

LEX11:57 amLexington Blue Grass

1h 47m

ORD12:44 pmChicago O'Hare Intl

$261

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Thu 8/27

10:36 am-1:16 pm

Nonstop1h 40m

Lexington Blue Grass

Thu 9/3

1:51 pm-2:35 pm

Nonstop1h 44m

$259

Quickest round-trip

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 8/29

2:59 pm-5:35 pm

Nonstop1h 36m

Lexington Blue Grass

Tue 9/1

1:58 pm-2:42 pm

Nonstop1h 44m

$259

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 9/25

2:57 pm-5:31 pm

Nonstop1h 34m

Lexington Blue Grass

Mon 9/28

5:23 am-6:10 am

Nonstop1h 47m

$259

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 8/28

3:54 pm-6:25 pm

Nonstop1h 31m

Lexington Blue Grass

Fri 9/4

6:59 pm-7:59 pm

Nonstop2h 00m

$259

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 8/26

3:00 pm-5:36 pm

Nonstop1h 36m

Lexington Blue Grass

Sun 8/30

7:00 am-7:45 am

Nonstop1h 45m

$259

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 11/6

8:15 am-10:56 am

Nonstop1h 41m

Lexington Blue Grass

Sun 11/8

11:26 am-12:14 pm

Nonstop1h 48m

$259

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 8/26

5:50 pm-8:28 pm

Nonstop1h 38m

Lexington Blue Grass

Sat 8/29

9:52 am-10:40 am

Nonstop1h 48m

$259

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Thu 9/17

7:11 am-5:50 pm

1 stop9h 39m

Lexington Blue Grass

Thu 9/24

6:40 pm-2:45 pm

1 stop21h 05m

$278

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 8/22

11:22 am-5:21 pm

1 stop4h 59m

Lexington Blue Grass

Sun 8/23

7:35 am-10:42 am

1 stop4h 07m

$279

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 8/28

6:40 am-12:11 pm

1 stop4h 31m

Lexington Blue Grass

Fri 9/4

10:52 am-4:17 pm

1 stop6h 25m

$279

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?

Prices are currently typical for flights on this route.

Typical prices usually range from $249 to $269.
The lowest price recently found on this route was $259.

What is the cheapest month to fly to Lexington?

In general, December 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 $265. If you are unable to visit Lexington during the month of December, then departing from Chicago during the month November is also very affordable. Most momondo users find prices during this month for around $275.

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 $264. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday 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 $493.

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 $297. Try not to purchase tickets in the afternoon because they tend to be around $430. 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

What cabin class options are available on Chicago to Lexington flights?

There are 4 cabin classes available to choose from on Chicago to Lexington flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Lexington flights?

You could potentially save up to 10% on your flight if you consider stops on a Chicago to Lexington flight.

How have Chicago to Lexington flight prices changed over time?

As of August 2026, prices for Chicago to Lexington flights are approximately 101% 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	$295
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 $295. The best round-trip flight deal from Chicago to Lexington found on momondo in the last 72 hours is $309.

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 August 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 30.77% of the total bookings. Other popular models include Canadair (Bombardier) Regional Jet 700 with 30.46%, Embraer 175 (Enhanced Winglets) with 20.00%, and Canadair (Bombardier) Regional Jet with 5.54%.
What is the most popular airline from Chicago to Lexington?
Based on momondo bookings for flights between Chicago and Lexington, the leading airline is United Airlines, making up 57% of the total bookings. Other popular airlines include American Airlines with 43%.

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 11,845 reviews		Search American Airlines flights
United Airlines	PriceFrom $189	Free Cancellation	Rating 7.4 10,059 reviews		Search United Airlines flights

United Airlines Flights From Chicago to Lexington
United Airlines operates around 25 flights from Chicago to Lexington every week. The average price of these flights found in the last 72 hours has been $410, 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 10,059 reviews.
American Airlines Flights From Chicago to Lexington
American Airlines (7.1/10 from 11,845 reviews) operates around 5 flights from Chicago to Lexington in any given week. The average American Airlines airfare for this route is around $283, 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

Winchester

Frankfort

Danville

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 $122

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 9/17. 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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Delta flights from Chicago to Lexington

Our best Delta deals on Chicago to Lexington flight tickets

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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?

What cabin class options are available on Chicago to Lexington flights?

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

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

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

Airports servicing Kentucky

Fly your favorite airline to Lexington

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Lexington

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

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