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$174 Cheap Flights from Chicago (ORD) to Lexington (LEX)

View $174 flight on Thu, Oct 22, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)

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Cheap Flights from Chicago to Lexington (ORD-LEX)

Prices were available within the past 7 days and start at $174 for one-way flights and $259 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, Sep 4 - Sun, Sep 6
ORD
Chicago
LEX
Lexington
$259 Roundtrip, found 4 hours ago
$259
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Chicago to Lexington, returning Sun, Sep 6, priced at $259 found 4 hours ago
United
Fri, Sep 4 - Sun, Sep 6
ORD
Chicago
LEX
Lexington
$259 Roundtrip, found 4 hours ago
$259
Roundtrip
found 4 hours ago
Select United flight, departing Fri, Sep 4 from Chicago to Lexington, returning Sun, Sep 6, priced at $259 found 4 hours ago
United
Thu, Sep 3 - Sun, Sep 6
ORD
Chicago
LEX
Lexington
$268 Roundtrip, found 4 hours ago
$268
Roundtrip
found 4 hours ago
Select United flight, departing Thu, Sep 3 from Chicago to Lexington, returning Sun, Sep 6, priced at $268 found 4 hours ago
American Airlines
Fri, Sep 4 - Sun, Sep 6
ORD
Chicago
LEX
Lexington
$269 Roundtrip, found 4 hours ago
$269
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Chicago to Lexington, returning Sun, Sep 6, priced at $269 found 4 hours ago
United
Fri, Sep 4 - Mon, Sep 7
ORD
Chicago
LEX
Lexington
$270 Roundtrip, found 5 hours ago
$270
Roundtrip
found 5 hours ago
Select United flight, departing Fri, Sep 4 from Chicago to Lexington, returning Mon, Sep 7, priced at $270 found 5 hours ago
United
Wed, Aug 26 - Wed, Sep 2
ORD
Chicago
LEX
Lexington
$274 Roundtrip, found 1 hour ago
$274
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Aug 26 from Chicago to Lexington, returning Wed, Sep 2, priced at $274 found 1 hour ago
Delta
Thu, Oct 22 - Sun, Oct 25
ORD
Chicago
LEX
Lexington
$279 Roundtrip, found 4 hours ago
$279
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Oct 22 from Chicago to Lexington, returning Sun, Oct 25, priced at $279 found 4 hours ago
American Airlines
Wed, Oct 28 - Sat, Oct 31
ORD
Chicago
LEX
Lexington
$282 Roundtrip, found 13 hours ago
$282
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Oct 28 from Chicago to Lexington, returning Sat, Oct 31, priced at $282 found 13 hours ago
American Airlines
Wed, Aug 26 - Wed, Sep 2
ORD
Chicago
LEX
Lexington
$284 Roundtrip, found 1 hour ago
$284
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Aug 26 from Chicago to Lexington, returning Wed, Sep 2, priced at $284 found 1 hour ago
United
Thu, Nov 5 - Sun, Nov 8
ORD
Chicago
LEX
Lexington
$285 Roundtrip, found 11 hours ago
$285
Roundtrip
found 11 hours ago
Select United flight, departing Thu, Nov 5 from Chicago to Lexington, returning Sun, Nov 8, priced at $285 found 11 hours ago

Alternative airports near Lexington

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Blue Grass LEX. Cheapest and Closest option available. Average driving time to city center is 9 minutes. Flights from $274
LEX
Blue Grass
CheapestClosest
Average driving time to city center9 min
Flights from $274

What you need to know for your flight from O'Hare Intl. to Blue Grass

Chicago (ORD) to Lexington (LEX) at a glance

Travel from Chicago (ORD) to Lexington (LEX) with a selection of airlines on this convenient domestic route. Explore various options for flights from Chicago, comparing full-service carriers to find the best itinerary that matches your budget and schedule. As you plan your trip, get ready to discover Lexington's renowned attractions and neighborhoods. Here, you'll find essential details about flights from O'Hare International Airport to Blue Grass Airport.

  • Fastest flight duration: around 1h 30m non-stop
  • Route distance: roughly 300 miles (485 km)
  • Flights per week: around 15+ flights with multiple daily departures on average
  • Typical fares (one-way): economy tickets often range from $95–$345, depending on seasonality and how far ahead you book

Flights from O'Hare International Airport (ORD) to Blue Grass Airport (LEX)

Based on the latest traveler bookings, here are the top airlines favored for flights from Chicago to Lexington, focusing on non-stop and one-stop options. Popular layover points include Detroit Metropolitan Wayne County Airport (DTW) with about a 1-hour layover and Charlotte-Douglas International Airport (CLT) offering around 1 hour and 45 minutes of waiting time. These choices allow you to balance price, total travel duration, and cabin class to craft the perfect itinerary.

  • American Airlines: This full-service airline provides both non-stop and one-stop flights, with one-way ticket prices generally falling between $95 and $355. It makes up about 50% of the departures on this route, offering a typical direct flight duration of 1 hour and 30 minutes.
  • United: Another full-service option, United offers non-stop flights, with one-way fares usually ranging from $95 to $390. It accounts for around 49% of the departures along this route, with an estimated journey time of 1 hour and 30 minutes.
  • Delta: Delta operates as a full-service carrier with one-stop flights, featuring one-way fares that typically range from $110 to $540. It represents approximately 1% of the departures on this route, with an in-flight duration of 3 hours and an overall travel time of about 5 hours, including layover.

Travelers flying from Chicago to Lexington can opt for an upgrade, with first-class service available on this route through both United and American Airlines.

Best time to fly from Chicago (ORD) to Lexington (LEX)

The most popular months for travelers flying from Chicago to Lexington are January, March, and April, when peak temperatures in Lexington reach up to 54.5°F in April. If you prefer quieter travel, consider July, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 75.4°F. For better deals, February usually offers the lowest average one-way fare around $177. Flight availability peaks in August and October, with approximately 18 flights per week, making it easier to find convenient departure times. February has the fewest flights, with approximately 12 flights per week.

  • Cheapest time to fly: February usually offers good deals with average one-way fare around $177, roughly 14% cheaper than the yearly average.
  • Another budget-friendly time to fly: March typically offers an average one-way fare of around $197.
  • Most flight options: August and October have the highest number of flights from Chicago to Lexington, with approximately 18 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January32.7°F (0.4°C)Moderately High13$226
February36.5°F (2.5°C)Average12$177
March45.1°F (7.3°C)Moderately High16$197
April54.5°F (12.5°C)Moderately High17$210
May64.2°F (17.9°C)Average16$203
June72.1°F (22.3°C)Average16$203
July75.4°F (24.1°C)Moderately Low14$203
August74.1°F (23.4°C)Average18$223
September68.2°F (20.1°C)Moderately Low16$204
October56.8°F (13.8°C)Average18$215
November45.0°F (7.2°C)Average16$205
December38.5°F (3.6°C)Moderately Low14$205

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Chicago (ORD) to Lexington (LEX)

  • Chicago to Lexington (MDW-LEX): Midway International Airport (MDW) is located approximately 16 miles from O'Hare International Airport (ORD).

How to find the best prices for flights from Chicago (ORD) to Lexington (LEX)

Getting some of the best deals on flights from Chicago to Lexington is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking 2-8 weeks in advance, although most travelers tend to book within 2 weeks. Morning departures, between 5 am and 12 pm, not only offer lower prices but are also the most popular flight times. Additionally, flying on Fridays provides both cheaper rates and is the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Blue Grass Airport from O'Hare International Airport

Lexington welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Lexington efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Lexington, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Blue Grass Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Blue Grass Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Blue Grass Airport, Versailles Seaport, a seaport, is located about 7.2 miles from the airport.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) cost?
You can find cheap one-way flights from $174 and cheap return flights from $259 Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) with Expedia. One-way flights usually range from $222 to $652, and return flights typically cost between $286 and $972. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
July is the cheapest month to fly from Chicago, IL (ORD) to Lexington, KY (LEX), with average round-trip fares around $284. This price is about 10% lower than the average throughout the year, as summer travel can lead to competitive pricing. Other economical months for this route include March and August.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
2 airlines operate nonstop service from ORD to LEX:

  • United operates around 43 direct flights from ORD to LEX every week
  • American Airlines operates around 27 direct flights from ORD to LEX every week

What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
American Airlines is one of the cheapest airlines offering nonstop flights from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass), with round-trip tickets starting from around $232. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
The best airline to fly with from Chicago, IL (ORD) to Lexington, KY (LEX) will differ from traveler to traveler. If you like to fly early, American Airlines offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. American Airlines offers the most daily flights from ORD to LEX, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
For flights from Chicago, IL (ORD) to Lexington, KY (LEX), the best times to fly are in July and August. These months are the cheapest, with return flights averaging around $284. July and August also provide warm weather, making it a great time to explore Lexington's outdoor attractions.*Prices based on flights available on Expedia in the last year.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
On average, there are around 10 nonstop flights per day from O'Hare Intl. (ORD) to Blue Grass (LEX). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
The earliest flight from Chicago, IL (ORD) to Lexington, KY (LEX) usually leaves at around 12:05 AM, operated by United and Delta. This seasonal service is active in December, allowing you to maximize your time in Lexington. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
The most popular departure times for flights from Chicago O'Hare International Airport (ORD) to Lexington (LEX) are in the early morning, from 6am to 9am. About 22% of passengers prefer this time window. Many major carriers, including American Airlines and Delta, offer flights during this window. This timing works well because it allows you to arrive in Lexington with plenty of time to start your day.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
A nonstop flight from ORD to LEX typically takes around 1 hour 30 minutes, covering approximately 324 miles. Connecting flights on this route usually add 3 hours 20 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
First class seats are offered on the ORD to LEX route. First class cabins are available on:

  • Delta Air Lines
  • American Airlines
  • United Airlines

How much is a business class flight from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
A direct, return business class ticket from Chicago (ORD) to Lexington (LEX) typically costs between $800 - $1,103. A non-stop, one-way business class flight is usually around $389 - $554. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Lexington from O'Hare Intl. (ORD)?
If you're planning to travel to Lexington from O'Hare Intl. (ORD), you can fly into Blue Grass (LEX) Some flights may connect through major hubs like Ronald Reagan Washington National (DCA), Raleigh - Durham Intl. (RDU), Baltimore Washington Intl. Thurgood Marshall (BWI) before reaching Lexington. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) Lexington Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Lexington, KY (LEX-Blue Grass) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Blue Grass
Airlines serving
American Airlines, Delta, United
Roundtrip price
$259
Distance
323 mi
Average flight time
2 hours 34 mins

Book with confidence

Chicago to Lexington Flights

The cheapest times to fly from Chicago to Lexington

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Lexington are during the month of September. You can find some of the cheapest flights from Chicago to Lexington with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Lexington

Sunday is one of the best days to book for cheap flights from Chicago to Lexington: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Lexington

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Lexington in 2026. You can also book with separate airlines for your outbound and return journeys, from $174 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Lexington flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Lexington airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Lexington Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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