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Cheap flights from Chicago to Lexington from $125

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 5/29. 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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0 bags

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Find the cheapest flights from Chicago to Lexington

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Lexington.
10:50 am - 1:24 pmORD-LEX
1h 34mnonstop
6:10 pm - 6:55 pmLEX-ORD
1h 45mnonstop
$215United Airlines
Find Deal
mar., abr. 29 - sáb., may. 3
9:15 pm - 11:44 pmORD-LEX
1h 29mnonstop
5:30 pm - 6:14 pmLEX-ORD
1h 44mnonstop
$230United Airlines
Find Deal
vie., abr. 25 - mar., abr. 29
9:15 pm - 11:44 pmORD-LEX
1h 29mnonstop
5:30 pm - 6:14 pmLEX-ORD
1h 44mnonstop
$232United Airlines
Find Deal
mié., abr. 23 - mié., abr. 30
3:02 pm - 9:34 pmMDW-LEX
5h 32m1 stop
6:00 am - 9:07 amLEX-MDW
4h 07m1 stop
$235Delta
Find Deal
mar., abr. 29 - sáb., may. 3
9:55 am - 2:57 pmORD-LEX
4h 02m1 stop
6:00 am - 12:20 pmLEX-ORD
7h 20m1 stop
$235Delta
Find Deal
mar., abr. 29 - sáb., may. 3
3:16 pm - 5:36 pmORD-LEX
1h 20mnonstop
8:06 pm - 12:11 amLEX-ORD
5h 05m1 stop
$239American Airlines
Find Deal
sáb., may. 10 - lun., may. 12
2:01 pm - 4:26 pmORD-LEX
1h 25mnonstop
6:10 pm - 11:49 pmLEX-ORD
6h 39m1 stop
$240American Airlines
Find Deal
mar., abr. 29 - sáb., may. 3
11:51 am - 5:35 pmORD-LEX
4h 44m1 stop
5:05 pm - 5:40 pmLEX-ORD
1h 35mnonstop
$242American Airlines
Find Deal
mié., abr. 23 - mié., abr. 30
3:32 pm - 1:24 pmORD-LEX
20h 52m2 stops
5:07 pm - 12:58 amLEX-ORD
8h 51m1 stop
mié., abr. 23 - jue., abr. 24
5:05 am - 4:17 pmORD-LEX
10h 12m1 stop
4:47 pm - 4:25 pmLEX-ORD
24h 38m2 stops
dom., may. 11 - dom., may. 18

United Airlines flights from Chicago to Lexington

Our best United Airlines deals on Chicago to Lexington flight tickets
United Airlines
Apr 29
ORD10:50 amChicago O'Hare Intl
1h 34m
LEX1:24 pmLexington Blue Grass
May 3
LEX6:10 pmLexington Blue Grass
1h 45m
ORD6:55 pmChicago O'Hare Intl
United Airlines
Apr 25
ORD9:15 pmChicago O'Hare Intl
1h 29m
LEX11:44 pmLexington Blue Grass
Apr 29
LEX5:30 pmLexington Blue Grass
1h 44m
ORD6:14 pmChicago O'Hare Intl
United Airlines
Apr 23
ORD9:15 pmChicago O'Hare Intl
1h 29m
LEX11:44 pmLexington Blue Grass
Apr 30
LEX5:30 pmLexington Blue Grass
1h 44m
ORD6:14 pmChicago O'Hare Intl

Delta flights from Chicago to Lexington

Our best Delta deals on Chicago to Lexington flight tickets
Delta
Apr 29
MDW3:02 pmChicago Midway
5h 32m
1 stop
LEX9:34 pmLexington Blue Grass
May 3
LEX6:00 amLexington Blue Grass
4h 07m
1 stop
MDW9:07 amChicago Midway
Delta
May 10
ORD5:57 pmChicago O'Hare Intl
4h 54m
1 stop
LEX11:51 pmLexington Blue Grass
May 12
LEX7:59 pmLexington Blue Grass
4h 59m
1 stop
ORD11:58 pmChicago O'Hare Intl
Delta
Apr 23
MDW12:48 pmChicago Midway
5h 28m
1 stop
LEX7:16 pmLexington Blue Grass
Apr 30
LEX1:05 pmLexington Blue Grass
4h 07m
1 stop
MDW4:12 pmChicago Midway

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, 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 $218. If you are unable to visit Lexington during the month of January, then departing from Chicago during the month December is also very affordable. Most momondo users find prices during this month for around $237.

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 $253. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday 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 $310.

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 $264. Try not to purchase tickets in the afternoon because they tend to be around $352. 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

How far in advance should I book a flight to Lexington?

You are more likely to see cheaper flights to Lexington from Chicago when booking 11 weeks ahead of your departure date. In general, you can expect to find flights to Lexington for around $274 when searching 11 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Lexington from Chicago for as low as $197 on momondo.

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.

How have Chicago to Lexington flight prices changed over time?

As of March 2025, prices for Chicago to Lexington flights are approximately 24% cheaper 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

$125

Fastest flight time

1h 20m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Lexington

1 airport
The best one-way flight to Lexington from Chicago in the past 72 hours is $125. The best round-trip flight deal from Chicago to Lexington found on momondo in the last 72 hours is $215.
The fastest flight from Chicago to Lexington takes 1h 20m
Direct flights go from Chicago to Lexington on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There is 1 airport near Lexington: Lexington Blue Grass (LEX)

  • 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 20m.

  • 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
United AirlinesPriceFrom $156Free CancellationRating
7.4
8,603 reviews
Search United Airlines flights
American AirlinesPriceFrom $156Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
  • United Airlines Flights From Chicago to Lexington

    United Airlines operates around 15 flights from Chicago to Lexington every week. The average price of these flights found in the last 72 hours has been $307, but momondo users have found United Airlines deals from Chicago to Lexington from as low as $156 round-trip. United Airlines has been scored 7.4/10 in 8,603 reviews.

  • American Airlines Flights From Chicago to Lexington

    American Airlines (7.2/10 from 10,000 reviews) operates around 4 flights from Chicago to Lexington in any given week. The average American Airlines airfare for this route is around $261, with deals from around $156 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
Berea
Winchester
Versailles
Midway
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.


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