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Cheap flights from Lexington to Chicago from $129

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Lexington to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:29 am - 6:08 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 39mnonstop
American Airlines Logo
8:06 am - 10:44 amORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 38mnonstop
$278American Airlines
Thu, Oct 15 - Thu, Oct 22
United Airlines Logo
5:50 pm - 6:43 pmLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 53mnonstop
United Airlines Logo
1:59 pm - 4:38 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 39mnonstop
$279United Airlines
Sat, Dec 26 - Wed, Dec 30
American Airlines Logo
11:13 am - 11:59 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 46mnonstop
American Airlines Logo
9:15 pm - 11:46 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 31mnonstop
$279American Airlines
Fri, Oct 2 - Sun, Oct 4
American Airlines Logo
5:29 am - 6:08 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 39mnonstop
American Airlines Logo
8:21 am - 10:56 amORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 35mnonstop
$279American Airlines
Sat, Oct 31 - Sun, Nov 1
United Airlines Logo
6:00 am - 6:45 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 45mnonstop
United Airlines Logo
5:50 pm - 8:28 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 38mnonstop
$279United Airlines
Sat, Oct 3 - Sat, Oct 10
United Airlines Logo
9:00 am - 9:40 amLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 40mnonstop
United Airlines Logo
5:55 pm - 8:35 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 40mnonstop
$279United Airlines
Wed, Nov 18 - Sat, Nov 21
American Airlines Logo
6:01 pm - 6:59 pmLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
1h 58mnonstop
American Airlines Logo
9:35 pm - 12:09 amORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
1h 34mnonstop
$279American Airlines
Fri, Oct 2 - Tue, Oct 6
Delta Logo
3:34 pm - 8:49 pmLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
6h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:59 pm - 12:05 amORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
7h 06m1 stop Atlanta Hartsfield-Jackson
$299Delta
Wed, Dec 2 - Tue, Dec 8
Delta Logo
10:40 am - 1:59 pmLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
4h 19m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:15 pm - 12:05 amORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
4h 50m1 stop Atlanta Hartsfield-Jackson
$299Delta
Wed, Dec 2 - Sun, Dec 6
Delta Logo
12:45 pm - 7:05 pmLEX  Lexington Blue Grass-ORD Chicago O'Hare Intl
7h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:39 am - 5:19 pmORD  Chicago O'Hare Intl-LEX Lexington Blue Grass
4h 40m1 stop Detroit Metropolitan Wayne County
$299Delta
Wed, Dec 2 - Mon, Dec 7

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American Airlines flights from Lexington to Chicago O'Hare Intl Airport

Our best American Airlines deals on Lexington to Chicago O'Hare Intl Airport flight tickets
American Airlines
Oct 15
LEX5:29 amLexington Blue Grass
1h 39m
ORD6:08 amChicago O'Hare Intl
Oct 22
ORD8:06 amChicago O'Hare Intl
1h 38m
LEX10:44 amLexington Blue Grass
$278
American Airlines
Sep 24
LEX5:23 amLexington Blue Grass
1h 47m
ORD6:10 amChicago O'Hare Intl
Sep 27
ORD8:10 amChicago O'Hare Intl
1h 32m
LEX10:42 amLexington Blue Grass
$280
American Airlines
Sep 24
LEX5:23 amLexington Blue Grass
1h 47m
ORD6:10 amChicago O'Hare Intl
Sep 27
ORD9:15 pmChicago O'Hare Intl
1h 31m
LEX11:46 pmLexington Blue Grass
$281

United Airlines flights from Lexington to Chicago O'Hare Intl Airport

Our best United Airlines deals on Lexington to Chicago O'Hare Intl Airport flight tickets
United Airlines
Oct 2
LEX10:11 amLexington Blue Grass
1h 48m
ORD10:59 amChicago O'Hare Intl
Oct 9
ORD9:20 pmChicago O'Hare Intl
1h 35m
LEX11:55 pmLexington Blue Grass
$279
United Airlines
Sep 19
LEX7:00 amLexington Blue Grass
1h 45m
ORD7:45 amChicago O'Hare Intl
Sep 25
ORD9:20 pmChicago O'Hare Intl
1h 35m
LEX11:55 pmLexington Blue Grass
$294
United Airlines
Sep 18
LEX10:10 amLexington Blue Grass
1h 48m
ORD10:58 amChicago O'Hare Intl
Sep 21
ORD9:30 pmChicago O'Hare Intl
1h 35m
LEX12:05 amLexington Blue Grass
$309

momondo Fare Finder

 
Use the filters below to find and compare flights from Lexington to Chicago O'Hare Intl Airport that are best for you.

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Fly to

Route

Depart

Return

Price

Cheapest round-trip

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Thu 10/15

5:29 am-6:08 am

Nonstop1h 39m

Chicago O'Hare Intl

Thu 10/22

8:06 am-10:44 am

Nonstop1h 38m

$278

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Sat 12/26

5:50 pm-6:43 pm

Nonstop1h 53m

Chicago O'Hare Intl

Wed 12/30

1:59 pm-4:38 pm

Nonstop1h 39m

$279

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Fri 10/2

11:13 am-11:59 am

Nonstop1h 46m

Chicago O'Hare Intl

Sun 10/4

9:15 pm-11:46 pm

Nonstop1h 31m

$279
Quickest round-trip

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Sat 10/31

5:29 am-6:08 am

Nonstop1h 39m

Chicago O'Hare Intl

Sun 11/1

8:21 am-10:56 am

Nonstop1h 35m

$279

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Sat 10/3

6:00 am-6:45 am

Nonstop1h 45m

Chicago O'Hare Intl

Sat 10/10

5:50 pm-8:28 pm

Nonstop1h 38m

$279

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Wed 11/18

9:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Sat 11/21

5:55 pm-8:35 pm

Nonstop1h 40m

$279

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Fri 10/2

6:01 pm-6:59 pm

Nonstop1h 58m

Chicago O'Hare Intl

Tue 10/6

9:35 pm-12:09 am

Nonstop1h 34m

$279

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Wed 12/2

3:34 pm-8:49 pm

1 stop6h 15m

Chicago O'Hare Intl

Tue 12/8

3:59 pm-12:05 am

1 stop7h 06m

$299

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Wed 12/2

10:40 am-1:59 pm

1 stop4h 19m

Chicago O'Hare Intl

Sun 12/6

6:15 pm-12:05 am

1 stop4h 50m

$299

LexingtonChicago

LEX Lexington Blue Grass - ORD Chicago O'Hare Intl

LEXORD

Lexington Blue Grass

Wed 12/2

12:45 pm-7:05 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 12/7

11:39 am-5:19 pm

1 stop4h 40m

$299

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 Chicago from

How to get the cheapest flight ticket from Lexington to Chicago O'Hare Intl Airport

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 Lexington and Chicago O'Hare Intl Airport?

Prices are currently typical for flights on this route.

Typical prices usually range from $259 to $309.
The lowest price recently found on this route was $279.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Lexington averaging around $222.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $427. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Lexington because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $865.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Lexington in the morning is the least expensive time of day to depart. momondo users have found prices as low as $511 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $751. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Lexington Blue Grass to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Lexington to Chicago O'Hare Intl Airport flights?

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

How have Lexington to Chicago O'Hare Intl Airport flight prices changed over time?

As of September 2026, prices for Lexington to Chicago O'Hare Intl Airport flights are approximately 15% more expensive when compared to flights at the same time last year.

When to book flights from Lexington to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Lexington to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Lexington to Chicago O'Hare Intl Airport (LEX to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Lexington to Chicago O'Hare Intl Airport

Best Price Found

$129

Fastest flight time

1h 45m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Lexington in the past 72 hours is $129. The best round-trip flight deal from Lexington to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $278.
The fastest flight from Lexington to Chicago O'Hare Intl Airport takes 1h 45m
Direct flights go from Lexington to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Lexington to Chicago O'Hare Intl Airport

  • How far is Lexington Blue Grass to Chicago O'Hare Intl by plane?

    The distance between Lexington Blue Grass and Chicago O'Hare Intl is about 326.3 mi. 1h 45m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Lexington Blue Grass Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Lexington Blue Grass Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Lexington Blue Grass Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Lexington Blue Grass Airport to Chicago O'Hare Intl 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 Lexington Blue Grass Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Lexington to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Lexington to Chicago O'Hare Intl Airport?

Best airlines flying from Lexington to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Lexington to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $189Free CancellationRating
7.4
10,171 reviews
Search United Airlines flights
American AirlinesPriceFrom $189Free CancellationRating
7.1
12,044 reviews
Search American Airlines flights

  • United Airlines Flights From Lexington to Chicago O'Hare Intl Airport

    United Airlines flight deals from Lexington to Chicago O'Hare Intl Airport start from $189 round-trip. Over the 17 United Airlines flights for this route in a normal week, average airfare is usually $292 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Lexington to Chicago O'Hare Intl Airport

    The best American Airlines deal for Lexington to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $189, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $298 round-trip. American Airlines operates 12 flights out of Lexington into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 12,044 American Airlines reviews by users on momondo have scored the airline at 7.1/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Schaumburg
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South Haven
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
Skokie

Why use momondo?

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

Finding the right flight to Chicago from Lexington 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 Chicago quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Lexington to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search for Lexington to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Lexington to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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