LEX - CHI

$120 Find Cheap Flights from Lexington to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Lexington to Chicago departing on 6/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Lexington to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Lexington to Chicago, as well as popular online travel agencies
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$232
Typical prices: $334-$252
Multiple Airlines
mar 6/16gio 6/18
LEX - ORD • 1 stop
Cheapest non-stop
$249
Typical prices: $334-$252
United Airlines
ven 6/5lun 6/8
LEX - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy is carry-on only for budget trips.
United's Priority Boarding secures overhead bin space.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $249 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 1h 48m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 6 weeks in advance save around 34% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 11% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Lexington to Chicago (LEX-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Lexington to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Lexington to Chicago

mar, giu 16 - gio, giu 18
Multiple Airlines Logo
1:17 pm - 12:43 pm
LEX
-
ORD
24h 26m
1 stop
Multiple Airlines Logo
5:10 am - 2:16 pm
ORD
-
LEX
8h 06m
1 stop
$232Multiple Airlines
mar, giu 16 - gio, giu 18
Multiple Airlines Logo
1:17 pm - 12:43 pm
LEX
-
ORD
24h 26m
1 stop
Multiple Airlines Logo
5:10 am - 2:16 pm
ORD
-
LEX
8h 06m
1 stop
$233Multiple Airlines
ven, giu 5 - lun, giu 8
United Airlines Logo
7:44 pm - 8:35 pm
LEX
-
ORD
1h 51mnonstop
United Airlines Logo
7:49 pm - 10:30 pm
ORD
-
LEX
1h 41mnonstop
$249United Airlines
gio, lug 2 - dom, lug 5
American Airlines Logo
8:10 pm - 12:01 am
LEX
-
ORD
4h 51m
1 stop
American Airlines Logo
9:43 pm - 12:13 am
ORD
-
LEX
1h 30mnonstop
$259American Airlines
ven, lug 10 - dom, lug 12
United Airlines Logo
7:44 pm - 8:35 pm
LEX
-
ORD
1h 51mnonstop
United Airlines Logo
6:45 am - 9:16 am
ORD
-
LEX
1h 31mnonstop
$260United Airlines
mer, lug 15 - dom, lug 19
American Airlines Logo
11:20 am - 11:59 am
LEX
-
ORD
1h 39mnonstop
American Airlines Logo
8:15 am - 10:49 am
ORD
-
LEX
1h 34mnonstop
$264American Airlines
ven, mag 29 - lun, giu 1
Delta Logo
3:32 pm - 9:09 pm
LEX
-
MDW
6h 37m
1 stop
Delta Logo
6:23 am - 12:19 pm
MDW
-
LEX
4h 56m
1 stop
$269Delta
ven, mag 29 - ven, giu 5
Allegiant Air Logo
8:46 pm - 10:24 am
LEX
-
RFD
14h 38m
1 stop
Allegiant Air Logo
7:53 pm - 12:42 pm
RFD
-
LEX
15h 49m
1 stop
$298Allegiant Air
lun, giu 29 - mer, set 16
Delta Logo
7:35 am - 12:41 pm
LEX
-
MDW
6h 06m
1 stop
Delta Logo
6:00 am - 12:35 pm
MDW
-
LEX
5h 35m
1 stop
$302Delta
ven, mag 29 - ven, giu 5
Allegiant Air Logo
9:44 pm - 8:31 am
LEX
-
RFD
35h 47m
2 stops
Allegiant Air Logo
7:53 pm - 12:42 pm
RFD
-
LEX
15h 49m
1 stop
$390Allegiant Air
Booking Insights

KAYAK's insights & trends for Lexington to Chicago flights

Get data-powered insights and trends into flights from Lexington to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Lexington to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Lexington to Chicago departing in June.

What is the cheapest Lexington to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Lexington to Chicago costs $277 on the route between Lexington (LEX) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Lexington to Chicago?

The average price of all round-trip flights from Lexington to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Friday and more expensive on a Sunday. On your return trip to Lexington, you should consider flying back on a Saturday, and avoid Mondays for better deals.

What is the cheapest month to fly from Lexington to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Lexington to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Lexington to Chicago is October, where tickets cost $167 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is $189 and $189 respectively.

Can I save money by flying with a layover from Lexington to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $341, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Lexington to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Lexington to Chicago, you should book around 6 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Expert advice

Expert advice for your flight from Lexington to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Jessica Macdonald

Jessica Macdonald

Expert on Lufthansa

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Good to know

Low seasonFebruary
Cheapest flight$120
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Lexington to Chicago O'Hare Airport

When to book flights from Lexington to Chicago

Are your dates flexible? Find out the best times to travel from Lexington to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Lexington to Chicago

  • What is the cheapest flight from Lexington to Chicago?

    In the last 3 days, the lowest price for a flight from Lexington to Chicago was $120 for a one-way ticket and $232 for a round-trip.

  • Do I need a passport to fly between Lexington and Chicago?

    No

  • Which airports will I be using when flying from Lexington to Chicago?

    On your way to Chicago, you’ll fly out from Lexington Blue Grass. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Lexington to Chicago?

    American Airlines, Delta, and Virgin Atlantic offer inflight Wi-Fi service on the Lexington to Chicago flight route.

  • Which aircraft models fly most regularly from Lexington to Chicago?

    The Canadair (Bombardier) Regional Jet CRJ-550 is the aircraft model that flies most regularly on the Lexington to Chicago flight route.

  • Which airline alliances offer flights from Lexington to Chicago?

    Star Alliance, and oneworld are the airline alliances operating flights between Lexington and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Lexington to Chicago?

    There are nonstop flights from Lexington to Chicago on a daily basis.

  • Which is the best airline for flights from Lexington to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Lexington to Chicago are United Airlines and American Airlines. With an average price for the route of $284 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $265 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Lexington to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Lexington to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Lexington to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Lexington is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Lexington to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Lexington with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Lexington to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Lexington up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Lexington to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $366 or less one-way and $404 or less round-trip.

Prefer to fly direct from Lexington to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Lexington Blue Grass to Chicago.
Find which airlines fly direct from Lexington Blue Grass Airport to Chicago, which days they fly and book direct flights.

Direct departures

Lexington Blue Grass to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Chicago to Lexington Blue Grass

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the top airlines flying from Lexington to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Lexington to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Lexington to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9680 reviews
8.1Crew
7.1Entertainment
7.7Boarding
7.3Comfort
6.6Food
Airline reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

8.0 ExcellentWendi, Apr 2026
MSP - ORD
Read more United Airlines reviews

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Delayed flight. Missed connection, AA put us on a later connecting flight. The connection flight was delayed 4 times and we had to deplane. Didnt get home until 3am, when I was supposed to be home at 8:30p. Zero compensation offered from American. I would not fly them again.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

Better snacks but flight and crew were amazing on this flight

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Everything you need to know for your flight from Lexington to Chicago

Information on your arrival and departure airports