CHI - LEX

$103 Find Cheap Flights from Chicago to Lexington - 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 Chicago to Lexington departing on 9/24. 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: $252-$323
United Airlines
Thu 9/3Sun 9/6
ORD - LEX • Non-stop
Cheapest non-stop
$237
Typical prices: $224-$346
United Airlines
Sat 8/22Sat 8/29
ORD - LEX • 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 36m
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 travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
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Flight Deals

Cheap Flights from Chicago to Lexington (CHI-LEX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Lexington 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 Chicago to Lexington

Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
9:20 pm - 11:55 pm
ORD
-
LEX
1h 35mnonstop
United Airlines Logo
6:15 pm - 7:05 pm
LEX
-
ORD
1h 50mnonstop
$237United Airlines
Thu, Aug 20 - Sun, Aug 23
United Airlines Logo
9:20 pm - 11:55 pm
ORD
-
LEX
1h 35mnonstop
United Airlines Logo
9:52 am - 10:40 am
LEX
-
ORD
1h 48mnonstop
$237United Airlines
Sat, Sep 12 - Sun, Sep 13
American Airlines Logo
9:15 pm - 11:46 pm
ORD
-
LEX
1h 31mnonstop
American Airlines Logo
5:23 am - 6:10 am
LEX
-
ORD
1h 47mnonstop
$237American Airlines
Thu, Sep 10 - Sun, Sep 13
American Airlines Logo
9:15 pm - 11:46 pm
ORD
-
LEX
1h 31mnonstop
American Airlines Logo
5:23 am - 6:10 am
LEX
-
ORD
1h 47mnonstop
$237American Airlines
Fri, Aug 28 - Mon, Aug 31
United Airlines Logo
9:20 pm - 11:55 pm
ORD
-
LEX
1h 35mnonstop
United Airlines Logo
9:52 am - 10:40 am
LEX
-
ORD
1h 48mnonstop
$237United Airlines
Sat, Aug 22 - Sat, Aug 29
United Airlines Logo
2:59 pm - 5:35 pm
ORD
-
LEX
1h 36mnonstop
United Airlines Logo
9:52 am - 10:40 am
LEX
-
ORD
1h 48mnonstop
$237United Airlines
Thu, Aug 27 - Sun, Aug 30
American Airlines Logo
9:15 pm - 11:46 pm
ORD
-
LEX
1h 31mnonstop
American Airlines Logo
6:48 am - 7:44 am
LEX
-
ORD
1h 56mnonstop
$237American Airlines
Mon, Aug 24 - Mon, Aug 31
Delta Logo
6:05 am - 12:11 pm
MDW
-
LEX
5h 06m
1 stop
Delta Logo
5:00 pm - 10:36 pm
LEX
-
MDW
6h 36m
1 stop
$257Delta
Wed, Sep 9 - Wed, Sep 16
Delta Logo
4:30 pm - 11:54 pm
MDW
-
LEX
6h 24m
1 stop
Delta Logo
10:08 am - 4:15 pm
LEX
-
MDW
7h 07m
1 stop
$257Delta
Sat, Aug 29 - Sun, Aug 30
Delta Logo
6:11 am - 12:11 pm
MDW
-
LEX
5h 00m
1 stop
Delta Logo
6:00 am - 9:59 am
LEX
-
MDW
4h 59m
1 stop
$257Delta
Booking Insights

KAYAK's insights & trends for Chicago to Lexington flights

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

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

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

Flight prices are below average for this route right now.

Flights to Lexington from Chicago usually cost between $249 and $269 in August.
The lowest price found in the past 5 days was $237 on United Airlines (Aug 20-Aug 23).

What is the cheapest Chicago to Lexington flight route?

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

The cheapest return flight from Chicago to Lexington costs $249 on the route between Chicago O'Hare Intl Airport (ORD) and Lexington (LEX). It is also the most popular route.

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Lexington, 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 Chicago to Lexington is August, where tickets cost $254 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $478 and $457 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $198 on average.

Expert advice

Expert advice for your flight from Chicago to Lexington

 
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
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

December

Cheapest flight

$103
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago O'Hare Airport to Lexington

When to book flights from Chicago to Lexington

Are your dates flexible? Find out the best times to travel from Chicago to Lexington 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 Chicago to Lexington

  • What is the cheapest flight from Chicago to Lexington?

    In the last 5 days, the lowest price for a flight from Chicago to Lexington was $103 for a one-way ticket and $237 for a round-trip.

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

    A passport is not required to fly from Chicago to Lexington.

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

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Lexington Blue Grass.

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

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

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

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

  • Which airline alliances offer flights from Chicago to Lexington?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Lexington are United Airlines and American Airlines. With an average price for the route of $465 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 $294 and an overall rating of 7.1.

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

    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 Chicago to Lexington.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Lexington from Chicago 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 Chicago to Lexington?

    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 Lexington with an airline and back to Chicago with another airline.

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

    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 Lexington from Chicago 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 Chicago to Lexington

  • Looking for a cheap flight? 25% of our users found flights on this route for $295 or less one-way and $264 or less round-trip.

Prefer to fly direct from Chicago to Lexington?

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

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from Chicago to Lexington

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Lexington. 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 Chicago to Lexington? 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
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
6.6Food
Airline reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

8.0 ExcellentArmedrest, Jul 2026
ORD - PAH
Read more United Airlines reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

The gate got changed several times and the flight was delayed over an hour. Awful experience

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

No Snacks or Entertainment. The flight was short, snacks should still be given.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

I was not given the option to get on a different flight even though I was going to miss my connection due to weather delays (I did). When I called early in the morning, they said it wasn't delayed long enough; though I knew it would be by the time it was time for the flight ... it was and by that time it was too late. I wasn't given the option to pre-board with my toddler, and the food service was less than normal due to delays .... at least that's what the crew said.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

Sat on the tarmac for a good half hour before take off

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

Information on your arrival and departure airports