LEX - CHI

$131 Find Cheap Flights from Lexington to Chicago - Compare and Save

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 10/29. 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

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Everything you should know

Cheapest round-trip
$237
Typical prices: $222-$346
American Airlines
Thu 8/27Mon 8/31
LEX - ORD • Non-stop
Cheapest non-stop
$237
Typical prices: $232-$301
United Airlines
Thu 9/10Sun 9/13
LEX - ORD • Non-stop
Top airlines
Cheapest • from $237 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 1h 49m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 36% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 19% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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Flight Deals
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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

Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
6:30 am - 7:26 am
LEX
-
ORD
1h 56mnonstop
American Airlines Logo
9:15 pm - 11:46 pm
ORD
-
LEX
1h 31mnonstop
$237American Airlines
Fri, Aug 28 - Sun, Aug 30
American Airlines Logo
6:30 am - 7:26 am
LEX
-
ORD
1h 56mnonstop
American Airlines Logo
9:15 pm - 11:46 pm
ORD
-
LEX
1h 31mnonstop
$237American Airlines
Thu, Sep 10 - Sun, Sep 13
United Airlines Logo
7:00 am - 7:45 am
LEX
-
ORD
1h 45mnonstop
United Airlines Logo
9:30 pm - 12:05 am
ORD
-
LEX
1h 35mnonstop
$237United Airlines
Sat, Aug 29 - Sun, Aug 30
United Airlines Logo
9:52 am - 10:40 am
LEX
-
ORD
1h 48mnonstop
United Airlines Logo
9:20 pm - 11:55 pm
ORD
-
LEX
1h 35mnonstop
$237United Airlines
Thu, Sep 10 - Sat, Sep 12
United Airlines Logo
10:10 am - 10:58 am
LEX
-
ORD
1h 48mnonstop
United Airlines Logo
9:30 pm - 12:05 am
ORD
-
LEX
1h 35mnonstop
$237United Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
6:30 am - 7:26 am
LEX
-
ORD
1h 56mnonstop
American Airlines Logo
9:15 pm - 11:46 pm
ORD
-
LEX
1h 31mnonstop
$237American Airlines
Thu, Sep 10 - Sun, Sep 13
American Airlines Logo
5:23 am - 6:10 am
LEX
-
ORD
1h 47mnonstop
American Airlines Logo
9:15 pm - 11:46 pm
ORD
-
LEX
1h 31mnonstop
$237American Airlines
Fri, Aug 21 - Sun, Aug 23
Delta Logo
6:00 am - 9:59 am
LEX
-
MDW
4h 59m
1 stop
Delta Logo
12:46 pm - 7:46 pm
MDW
-
LEX
6h 00m
1 stop
$257Delta
Sat, Aug 22 - Wed, Aug 26
Delta Logo
4:30 pm - 10:36 pm
LEX
-
MDW
7h 06m
1 stop
Delta Logo
6:05 am - 12:11 pm
MDW
-
LEX
5h 06m
1 stop
$257Delta
Mon, Aug 17 - Sun, Aug 23
Delta Logo
7:35 am - 12:39 pm
LEX
-
MDW
6h 04m
1 stop
Delta Logo
6:05 am - 12:11 pm
MDW
-
LEX
5h 06m
1 stop
$257Delta
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 August.

Flight prices are below average for this route right now.

Flights to Chicago from Lexington usually cost between $252 and $453 in August.
The lowest price found in the past 5 days was $237 on American Airlines (Aug 22-Aug 26).

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 $249 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 Sundays 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 February, where tickets cost $238 (return) on average. On the other hand, the most expensive months are May and April, where the average cost of round-trip tickets is $342 and $341 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 $339, 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 3 weeks before departure, which saves you about 36% 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.

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.

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.

Good to know

Low season

February

Cheapest flight

$131
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 14% increase in price.
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 5 days, the lowest price for a flight from Lexington to Chicago was $131 for a one-way ticket and $237 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 Alaska Airlines 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 $340 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 $273 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 $290 or less one-way and $361 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 10046 reviews
7.7Boarding
7.3Comfort
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

Gluten free snack options and meals that offer both gluten free and dairy free.

8.0 ExcellentAnonymous, Jul 2026
PHX - ORD
Read more United Airlines reviews

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

The male air hostess was rude and didn’t provide good customer service. Didn’t even offer me a drink

This trip was a Christmas gift to our family. We were flying from Lexington to Palm Springs. When we were checking in the ticket agent said one bags was over weight by 4 LBS. We were flying first class which has baggage weight of 70 LBS per bag, one bag was 54LBS. We then had to take items from one bag to another. The agent also saw we had a dog with us. Once on the plane we were seated with the dog in the carrier. The United ticket agent came in the plane with two other people, I believe one was TSA and the other some security officer. The United agent said we had not paid for the dog ticket. We had paid for the ticket when we purchased our tickets. She did not give me time to find the email receipt. She then threatened all three of us with either I come with her or she would have all three of physically removed from the plane. I left the plane to pay for another ticket. She had to take my credit back to where we checked in. She acted as if it needed to be done immediately. She said we had 3 minutes. We then sat at the gate for approximately another 45 minutes. This was so embarrassing…to be threatened to be removed from a plane that we paid for all tickets including the dog. The flight attendance on the next leg of our trip were not very attentive to the passengers. On the plus side all the flights were on time. All in all, this was a miserable way to start a holiday vacation. United Airlines showed no compassion towards the whole incident. I feel we were purposely neglected.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

Better perks for corporate employees whom travel often and spend a lot of money with the airlines. Snacks were terrible chips crackers are ideas. Flight and crew were great comfort was fine entertainment not so great so so called status members means nothing

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.

Better snacks but flight and crew were amazing on this flight

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

They needed to de-ice the plane. Apparently airlines have a problem keeping their de-icing vehicles in good repair. After we backed away from the gate we sat and didn't move for nearly an hour. Nearly an HOUR with minimal communication from the flight crew. Eventually the sun took care of what American Airlines could not and melted the minimal ice. We finally took of a hour late which, in turn, jacked up our connection in Chicago.

We were delayed in Charlotte for almost 2 hours because American Airlines didn't have flight attendants for our flight.

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

Information on your arrival and departure airports