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Cheap flights from Chicago to Lexington from $86

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 4/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Lexington

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
8:46 pm - 2:57 pm
ORD
-
LEX
17h 11m
1 stop
American Airlines Logo
4:27 pm - 5:18 pm
LEX
-
ORD
1h 51mnonstop
$247American Airlines
Fri, Apr 24 - Sat, Apr 25
American Airlines Logo
8:06 am - 10:42 am
ORD
-
LEX
1h 36mnonstop
American Airlines Logo
6:53 pm - 7:46 pm
LEX
-
ORD
1h 53mnonstop
$249American Airlines
Wed, May 27 - Mon, Jun 1
Multiple Airlines Logo
1:27 pm - 8:41 am
ORD
-
LEX
18h 14m
1 stop
Multiple Airlines Logo
9:51 am - 10:59 pm
LEX
-
ORD
14h 08m
1 stop
$258Multiple Airlines
Sat, May 2 - Thu, May 7
American Airlines Logo
11:55 am - 7:45 pm
ORD
-
LEX
6h 50m
1 stop
American Airlines Logo
6:53 pm - 7:46 pm
LEX
-
ORD
1h 53mnonstop
$259American Airlines
Wed, May 27 - Mon, Jun 1
United Airlines Logo
2:33 pm - 5:10 pm
ORD
-
LEX
1h 37mnonstop
United Airlines Logo
6:01 pm - 6:50 pm
LEX
-
ORD
1h 49mnonstop
$264United Airlines
Wed, Apr 1 - Wed, Apr 8
Delta Logo
5:40 am - 1:38 pm
MDW
-
LEX
6h 58m
1 stop
Delta Logo
8:04 am - 12:42 pm
LEX
-
MDW
5h 38m
1 stop
$269Delta
Sat, May 2 - Thu, May 7
Delta Logo
9:49 am - 5:13 pm
ORD
-
LEX
6h 24m
1 stop
Delta Logo
8:20 pm - 11:59 pm
LEX
-
ORD
4h 39m
1 stop
$269Delta
Wed, May 27 - Mon, Jun 1
American Airlines Logo
8:00 am - 10:31 am
ORD
-
LEX
1h 31mnonstop
American Airlines Logo
6:00 am - 10:11 am
LEX
-
ORD
5h 11m
1 stop
$270American Airlines
Tue, May 5 - Tue, May 12
United Airlines Logo
4:32 pm - 7:09 pm
ORD
-
LEX
1h 37mnonstop
United Airlines Logo
7:44 pm - 8:35 pm
LEX
-
ORD
1h 51mnonstop
$277United Airlines
Fri, Jun 5 - Sun, Jun 7
Multiple Airlines Logo
5:50 am - 8:41 am
ORD
-
LEX
25h 51m
2 stops
Multiple Airlines Logo
9:51 am - 12:27 am
LEX
-
ORD
15h 36m
1 stop
$278Multiple Airlines
Sat, May 2 - Thu, May 7

Delta flights from Chicago to Lexington

Our best Delta deals on Chicago to Lexington flight tickets
Delta
May 2
MDW5:40 amChicago Midway
6h 58m
1 stop
LEX1:38 pmLexington Blue Grass
May 7
LEX8:04 amLexington Blue Grass
5h 38m
1 stop
MDW12:42 pmChicago Midway
$269
Delta
Apr 8
MDW6:00 amChicago Midway
6h 39m
1 stop
LEX1:39 pmLexington Blue Grass
Apr 15
LEX7:40 amLexington Blue Grass
6h 03m
1 stop
MDW12:43 pmChicago Midway
$284
Delta
Apr 3
MDW1:10 pmChicago Midway
2h 57m
1 stop
LEX5:07 pmLexington Blue Grass
Apr 7
LEX7:45 amLexington Blue Grass
5h 44m
1 stop
MDW12:29 pmChicago Midway
$299

American Airlines flights from Chicago to Lexington

Our best American Airlines deals on Chicago to Lexington flight tickets
American Airlines
Apr 24
ORD8:46 pmChicago O'Hare Intl
17h 11m
1 stop
LEX2:57 pmLexington Blue Grass
Apr 25
LEX4:27 pmLexington Blue Grass
1h 51m
ORD5:18 pmChicago O'Hare Intl
$247
American Airlines
May 27
ORD8:06 amChicago O'Hare Intl
1h 36m
LEX10:42 amLexington Blue Grass
Jun 1
LEX6:53 pmLexington Blue Grass
1h 53m
ORD7:46 pmChicago O'Hare Intl
$249
American Airlines
May 27
ORD11:55 amChicago O'Hare Intl
6h 50m
1 stop
LEX7:45 pmLexington Blue Grass
Jun 1
LEX6:53 pmLexington Blue Grass
1h 53m
ORD7:46 pmChicago O'Hare Intl
$259

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Lexington 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, momondo users made 832,500 searches. Data last updated March 22, 2026.
Use the filters below to find and compare flights from Chicago to Lexington that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 4/24

8:46 pm-2:57 pm

1 stop17h 11m

Lexington Blue Grass

Sat 4/25

4:27 pm-5:18 pm

Nonstop1h 51m

$247

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 5/27

8:06 am-10:42 am

Nonstop1h 36m

Lexington Blue Grass

Mon 6/1

6:53 pm-7:46 pm

Nonstop1h 53m

$249

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 5/2

1:27 pm-8:41 am

1 stop18h 14m

Lexington Blue Grass

Thu 5/7

9:51 am-10:59 pm

1 stop14h 08m

$258

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 5/27

11:55 am-7:45 pm

1 stop6h 50m

Lexington Blue Grass

Mon 6/1

6:53 pm-7:46 pm

Nonstop1h 53m

$259
Quickest round-trip

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 4/1

2:33 pm-5:10 pm

Nonstop1h 37m

Lexington Blue Grass

Wed 4/8

6:01 pm-6:50 pm

Nonstop1h 49m

$264

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Sat 5/2

5:40 am-1:38 pm

1 stop6h 58m

Lexington Blue Grass

Thu 5/7

8:04 am-12:42 pm

1 stop5h 38m

$269

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Wed 5/27

9:49 am-5:13 pm

1 stop6h 24m

Lexington Blue Grass

Mon 6/1

8:20 pm-11:59 pm

1 stop4h 39m

$269

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Tue 5/5

8:00 am-10:31 am

Nonstop1h 31m

Lexington Blue Grass

Tue 5/12

6:00 am-10:11 am

1 stop5h 11m

$270

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Fri 6/5

4:32 pm-7:09 pm

Nonstop1h 37m

Lexington Blue Grass

Sun 6/7

7:44 pm-8:35 pm

Nonstop1h 51m

$277

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Sat 5/2

5:50 am-8:41 am

2 stops25h 51m

Lexington Blue Grass

Thu 5/7

9:51 am-12:27 am

1 stop15h 36m

$278

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Lexington from

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

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, May 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 $238. If you are unable to visit Lexington during the month of May, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around $249.

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 $457.

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 $395. 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 Blue Grass flights?

There are 4 cabin classes available to choose from on Chicago to Lexington Blue Grass 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?

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 March 2026, prices for Chicago to Lexington flights are approximately 69% 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

$213

Fastest flight time

1h 24m

Direct flights

Every day

Airports in Lexington

1 airport
The best one-way flight to Lexington from Chicago in the past 72 hours is $213. The best round-trip flight deal from Chicago to Lexington found on momondo in the last 72 hours is $279.
The fastest flight from Chicago to Lexington takes 1h 24m
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

  • 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 24m.

  • 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?

  • 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?

  • What is the most popular airline 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
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $189Free CancellationRating
7.1
11,489 reviews
Search American Airlines flights
United AirlinesPriceFrom $189Free CancellationRating
7.4
9,455 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago to Lexington

    United Airlines operates around 28 flights from Chicago to Lexington every week. The average price of these flights found in the last 72 hours has been $349, 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 9,455 reviews.

  • American Airlines Flights From Chicago to Lexington

    American Airlines (7.1/10 from 11,489 reviews) operates around 17 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.

Traveling to a place near Lexington?

Book flights to Lexington if you plan to visit one of these locations
Richmond
Somerset
Georgetown
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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