CHI - LEX

$120 Find Cheap Flights from Chicago to Lexington

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 5/14. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Lexington

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

Cheap Flights from Chicago to Lexington

 
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.

Recent round-trip flight deals from Chicago to Lexington

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Lexington.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
9:30 am - 12:00 pmORD-LEX
1h 30mnonstop
American Airlines Logo
6:04 am - 6:40 amLEX-ORD
1h 36mnonstop
$189American Airlines
Find Deal
Fri, Jul 25 - Sun, Jul 27
American Airlines Logo
3:16 pm - 5:36 pmORD-LEX
1h 20mnonstop
American Airlines Logo
6:12 pm - 6:45 pmLEX-ORD
1h 33mnonstop
$190American Airlines
Find Deal
Thu, May 22 - Sun, May 25
United Airlines Logo
6:30 pm - 9:09 pmORD-LEX
1h 39mnonstop
United Airlines Logo
5:58 pm - 6:40 pmLEX-ORD
1h 42mnonstop
$206United Airlines
Find Deal
Thu, May 22 - Mon, May 26
Delta Logo
1:08 pm - 5:09 pmMDW-LEX
3h 01m1 stop
Delta Logo
4:45 pm - 9:13 pmLEX-MDW
5h 28m1 stop
$209Delta
Find Deal
Wed, May 21 - Sat, May 24
Delta Logo
1:45 pm - 8:55 pmORD-LEX
6h 10m1 stop
Delta Logo
11:59 am - 4:30 pmLEX-ORD
5h 31m1 stop
$209Delta
Find Deal
Fri, May 23 - Sun, May 25
United Airlines Logo
6:30 pm - 9:09 pmORD-LEX
1h 39mnonstop
United Airlines Logo
7:00 am - 7:51 amLEX-ORD
1h 51mnonstop
$254United Airlines
Find Deal
Fri, Jun 13 - Fri, Jun 20
 Logo
5:50 pm - 7:54 amORD-LEX
13h 04m2 stops
 Logo
9:27 am - 4:55 pmLEX-ORD
32h 28m2 stops
Fri, Jun 13 - Sun, Jun 15
Allegiant Air Logo
8:36 pm - 9:50 pmMDW-LEX
24h 14m2 stops
Allegiant Air Logo
10:44 pm - 8:22 amLEX-MDW
10h 38m1 stop
$313Allegiant Air
Find Deal
Fri, Jun 13 - Sun, Jun 15
 Logo
9:55 am - 6:49 pmORD-LEX
7h 54m1 stop
 Logo
10:00 am - 12:05 amLEX-ORD
15h 05m2 stops
Thu, May 22 - Sun, May 25
Allegiant Air Logo
8:36 pm - 9:50 pmMDW-LEX
24h 14m2 stops
Allegiant Air Logo
9:27 am - 2:03 pmLEX-MDW
29h 36m2 stops
$342Allegiant Air
Find Deal
Fri, Jun 13 - Sun, Jun 15
Expert advice

Expert advice for your flight from Chicago to Lexington

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Main Cabin Extra offers early boarding and complimentary drinks for a small fee.


Download the American Airlines app for access to inflight entertainment.

United Airlines

United's Economy Plus offers up to 6 inches more legroom for added comfort.


Purchase Priority Boarding to ensure overhead bin space for your carry-on.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

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.

Read more
Useful Info

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.

What is the cheapest Chicago to Lexington flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Lexington.

Our data shows that the cheapest route for a return flight from Chicago to Lexington cost $217 and was between Chicago O'Hare Intl Airport (ORD) and Lexington (LEX). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $217.

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 Friday. 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 January, where tickets cost $218 (return) on average. On the other hand, the most expensive months are June and August, where the average cost of round-trip tickets is $349 and $349 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Chicago to Lexington, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonJuly
High seasonOctober
Cheapest flight$120
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 0% 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 3 days, the lowest price for a flight from Chicago to Lexington was $120 for a one-way ticket and $189 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?

    Only American Airlines offers 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 Star Alliance 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 $320 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 $268 and an overall rating of 7.2.

  • 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 $155 or less one-way and $259 or less round-trip.

Prefer to fly direct from Chicago to Lexington?

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
See more direct flights

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 8696 reviews
6.6Food
7.7Boarding
7.3Comfort
7.1Entertainment
8.1Crew
Airline reviews

A bit rush for transit. Food and entertainment are not available

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

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

Information on your arrival and departure airports

Compare transportation modes for Chicago to Lexington

Average priceAverage duration
Flights$2881h 20m
Buses$1178h 42m

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