Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Lexington to Chicago from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Lexington to Chicago departing on 2/7. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Lexington to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Lexington to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Lexington to Chicago.

Cheap last minute flights

Planning a quick getaway from Lexington to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Lexington to Chicago

Find recent round-trip train or bus tickets from Lexington to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
3:38 pm - 4:15 pmLEX-ORD
1h 37mnonstop
10:30 am - 1:00 pmORD-LEX
1h 30mnonstop
$217American Airlines
Find Deal
Thu, Jan 30 - Sat, Feb 1
6:50 am - 7:26 amLEX-ORD
1h 36mnonstop
8:35 pm - 11:05 pmORD-LEX
1h 30mnonstop
$219American Airlines
Find Deal
Thu, Jan 30 - Sun, Feb 2
7:40 am - 1:05 pmLEX-MDW
6h 25m1 stop
2:08 pm - 9:38 pmMDW-LEX
6h 30m1 stop
$237Delta
Find Deal
Thu, Feb 13 - Mon, Feb 17
1:11 pm - 5:25 pmLEX-ORD
5h 14m1 stop
10:30 am - 5:13 pmORD-LEX
5h 43m1 stop
$237Delta
Find Deal
Thu, Jan 30 - Sun, Feb 2
3:35 pm - 4:14 pmLEX-ORD
1h 39mnonstop
8:09 pm - 10:28 pmORD-LEX
1h 19mnonstop
$238American Airlines
Find Deal
Wed, Feb 26 - Thu, Mar 6
11:26 am - 3:40 pmLEX-ORD
5h 14m1 stop
1:30 pm - 3:56 pmORD-LEX
1h 26mnonstop
$246American Airlines
Find Deal
Tue, Feb 4 - Fri, Feb 14
11:56 am - 5:24 pmLEX-ORD
6h 28m1 stop
10:30 am - 1:00 pmORD-LEX
1h 30mnonstop
$248American Airlines
Find Deal
Thu, Jan 30 - Sat, Feb 1
7:00 am - 7:44 amLEX-ORD
1h 44mnonstop
10:47 am - 1:13 pmORD-LEX
1h 26mnonstop
$291United Airlines
Find Deal
Wed, Feb 26 - Wed, Feb 26
7:13 pm - 11:20 amLEX-ORD
17h 07m2 stops
8:30 am - 6:23 pmORD-LEX
8h 53m1 stop
Thu, Jan 30 - Sun, Feb 2
7:00 am - 7:54 amLEX-ORD
1h 54mnonstop
8:00 pm - 10:29 pmORD-LEX
1h 29mnonstop
$399United Airlines
Find Deal
Wed, Feb 5 - Wed, Feb 5
6:50 am - 7:26 amLEX-ORD
1h 36mnonstop
$109American Airlines
Find Deal
Fri, Feb 7
12:04 pm - 4:13 pmLEX-ORD
5h 09m1 stop
$119Delta
Find Deal
Wed, Feb 5
5:45 pm - 6:36 pmLEX-ORD
1h 51mnonstop
$139United Airlines
Find Deal
Tue, Mar 4
8:20 pm - 11:50 pmLEX-ORD
4h 30m1 stop
$140American Airlines
Find Deal
Mon, Apr 7
3:00 pm - 8:34 pmLEX-ORD
6h 34m1 stop
$149Delta
Find Deal
Sat, Jul 5
5:59 pm - 8:45 pmLEX-ORD
3h 46m1 stop
$170Delta
Find Deal
Fri, Apr 11
6:40 am - 7:17 amLEX-ORD
1h 37mnonstop
$179American Airlines
Find Deal
Fri, Mar 14
5:30 pm - 6:22 pmLEX-ORD
1h 52mnonstop
$189United Airlines
Find Deal
Sun, Mar 9
11:20 am - 12:05 pmLEX-ORD
1h 45mnonstop
$194United Airlines
Find Deal
Sat, Jul 5
9:40 am - 5:55 amLEX-ORD
21h 15m3 stops
Mon, Jan 13
7:03 am - 1:43 pmLEX-ORD
7h 40m1 stop
10:30 am - 5:13 pmORD-LEX
5h 43m1 stop
$619Delta
Find Deal
Fri, Jan 10 - Sun, Jan 12
5:56 am - 9:55 amLEX-ORD
4h 59m1 stop
10:30 am - 5:13 pmORD-LEX
5h 43m1 stop
$651Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
3:38 pm - 4:15 pmLEX-ORD
1h 37mnonstop
4:30 pm - 11:58 pmORD-LEX
6h 28m1 stop
$728American Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
5:56 am - 9:55 amLEX-ORD
4h 59m1 stop
4:58 pm - 9:41 pmORD-LEX
3h 43m1 stop
$729Delta
Find Deal
Sat, Jan 11 - Sun, Jan 12
11:26 am - 3:40 pmLEX-ORD
5h 14m1 stop
6:30 pm - 11:58 pmORD-LEX
4h 28m1 stop
$738American Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:13 pm - 5:20 pmLEX-ORD
23h 07m2 stops
6:55 am - 6:23 pmORD-LEX
10h 28m1 stop
Thu, Jan 9 - Sun, Jan 12
6:50 am - 7:26 amLEX-ORD
1h 36mnonstop
8:35 pm - 11:05 pmORD-LEX
1h 30mnonstop
$834American Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
2:08 pm - 2:55 pmLEX-ORD
1h 47mnonstop
10:50 am - 1:18 pmORD-LEX
1h 28mnonstop
$904United Airlines
Find Deal
Fri, Jan 10 - Sun, Jan 12
5:50 pm - 6:40 pmLEX-ORD
1h 50mnonstop
10:50 am - 1:18 pmORD-LEX
1h 28mnonstop
$959United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:13 pm - 12:55 pmLEX-ORD
18h 42m3 stops
8:30 am - 6:23 pmORD-LEX
8h 53m1 stop
$1,013
Find Deal
Thu, Jan 9 - Sun, Jan 12
3:38 pm - 4:15 pmLEX-ORD
1h 37mnonstop
10:30 am - 1:00 pmORD-LEX
1h 30mnonstop
$217American Airlines
Find Deal
Thu, Jan 30 - Sat, Feb 1
6:50 am - 7:26 amLEX-ORD
1h 36mnonstop
8:35 pm - 11:05 pmORD-LEX
1h 30mnonstop
$219American Airlines
Find Deal
Thu, Jan 30 - Sun, Feb 2
6:30 am - 7:02 amLEX-ORD
1h 32mnonstop
8:09 pm - 10:28 pmORD-LEX
1h 19mnonstop
$238American Airlines
Find Deal
Wed, Feb 26 - Thu, Mar 6
6:40 am - 7:17 amLEX-ORD
1h 37mnonstop
1:11 pm - 3:29 pmORD-LEX
1h 18mnonstop
$287American Airlines
Find Deal
Thu, Apr 3 - Sun, Apr 6
6:40 am - 7:11 amLEX-ORD
1h 31mnonstop
7:54 pm - 10:17 pmORD-LEX
1h 23mnonstop
$296American Airlines
Find Deal
Fri, Mar 7 - Sun, Mar 9
6:40 am - 7:17 amLEX-ORD
1h 37mnonstop
7:54 pm - 10:17 pmORD-LEX
1h 23mnonstop
$316American Airlines
Find Deal
Tue, Mar 11 - Sun, Mar 16
7:00 am - 7:54 amLEX-ORD
1h 54mnonstop
10:50 am - 1:18 pmORD-LEX
1h 28mnonstop
$377United Airlines
Find Deal
Wed, Jan 22 - Sat, Jan 25
1:59 pm - 2:35 pmLEX-ORD
1h 36mnonstop
2:28 pm - 4:54 pmORD-LEX
1h 26mnonstop
$399United Airlines
Find Deal
Wed, Feb 19 - Sat, Feb 22
7:00 am - 7:54 amLEX-ORD
1h 54mnonstop
2:38 pm - 5:08 pmORD-LEX
1h 30mnonstop
$499United Airlines
Find Deal
Sat, Jan 18 - Mon, Jan 20

United Airlines flights from Lexington to Chicago

Our best United Airlines deals on Lexington to Chicago flight tickets
United Airlines
Feb 26
LEX7:00 amLexington Blue Grass
1h 44m
ORD7:44 amChicago O'Hare Intl
Feb 26
ORD10:47 amChicago O'Hare Intl
1h 26m
LEX1:13 pmLexington Blue Grass
United Airlines
Jan 22
LEX7:00 amLexington Blue Grass
1h 54m
ORD7:54 amChicago O'Hare Intl
Jan 25
ORD10:50 amChicago O'Hare Intl
1h 28m
LEX1:18 pmLexington Blue Grass
United Airlines
Feb 5
LEX7:00 amLexington Blue Grass
1h 54m
ORD7:54 amChicago O'Hare Intl
Feb 5
ORD8:00 pmChicago O'Hare Intl
1h 29m
LEX10:29 pmLexington Blue Grass

Delta flights from Lexington to Chicago

Our best Delta deals on Lexington to Chicago flight tickets
Delta
Jan 30
LEX1:11 pmLexington Blue Grass
5h 14m
1 stop
ORD5:25 pmChicago O'Hare Intl
Feb 2
ORD10:30 amChicago O'Hare Intl
5h 43m
1 stop
LEX5:13 pmLexington Blue Grass
Delta
Feb 13
LEX5:53 pmLexington Blue Grass
4h 00m
1 stop
ORD8:53 pmChicago O'Hare Intl
Feb 16
ORD6:59 amChicago O'Hare Intl
3h 25m
1 stop
LEX11:24 amLexington Blue Grass
Delta
Feb 12
LEX5:56 amLexington Blue Grass
7h 03m
1 stop
MDW11:59 amChicago Midway
Feb 12
MDW5:05 pmChicago Midway
5h 43m
1 stop
LEX11:48 pmLexington Blue Grass

See travel insights to Chicago from

How to get the cheapest flight ticket from Lexington to Chicago

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?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Lexington, with most prices found around $217. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Lexington to Chicago during September average around $234.

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

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $248. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Lexington to Chicago for around $441.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Lexington to Chicago during this time can be as low as $239. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $284.

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

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

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

The best time to book a flight to Chicago from Lexington is 43 days out, which is when prices tend to be around $278. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $138.

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

There are 4 cabin classes available to choose from on Lexington Blue Grass to Chicago 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 flight prices changed over time?

As of January 2025, prices for Lexington to Chicago flights are approximately 201% more expensive when compared to flights at the same time last year.

When to book flights from Lexington to Chicago

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

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

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

Best Price Found

$109

Fastest flight time

1h 33m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Lexington in the past 72 hours is $109. The best round-trip flight deal from Lexington to Chicago found on momondo in the last 72 hours is $217.
The fastest flight from Lexington to Chicago takes 1h 33m
Direct flights go from Lexington to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Lexington Blue Grass to Chicago by plane?

    The distance between Lexington Blue Grass and Chicago is about 312.4 mi. 1h 36m is a normal flight duration for this route.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Lexington to Chicago?

  • What is the most popular airline from Lexington to Chicago?


Best airlines flying from Lexington to Chicago

Compare and see reviews for airlines that fly from Lexington to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $147Free CancellationRating
7.4
8,939 reviews
Search United Airlines flights
American AirlinesPriceFrom $153Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
  • United Airlines Flights From Lexington to Chicago

    United Airlines flies from Lexington to Chicago around 20 times per week, with 8,939 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Lexington to Chicago in the last 72 hours was $147 (round-trip), much lower than the average airfare cost of $266 for United Airlines flights on this route.

  • American Airlines Flights From Lexington to Chicago

    The best American Airlines deal for Lexington to Chicago flight tickets found on momondo in the last 72 hours was $153, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $255 round-trip. American Airlines operates 8 flights out of Lexington into Chicago in an average week, so prices vary by time and availability. 10,000 American Airlines reviews by users on momondo have scored the airline at 7.2/10.


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 enables you to select and highlight flights to Chicago from Lexington with this policy.

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

Once all potential Lexington to Chicago 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 Lexington to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Lexington. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


An easier way to manage your Chicago 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.
1 adult
From?
To?
Mon 1/13
Mon 1/20
Email me momondo's favorite deals

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago