Cheap flights from Chicago to Lexington

Chicago FSS
CHI
Blue Grass
LEX

Flight deals from Chicago to Lexington

Below you can see the best deals on flights Chicago — Lexington for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 14 October, from $243.

Top 10 cheap flights from Chicago to Lexington

DL
DL
$ 271

Chicago — Lexington

06:40—11:44
16 Sep 2026
4 h 4 m
1 stop
DL
DL
$ 271

Chicago — Lexington

06:05—11:44
16 Sep 2026
4 h 39 m
1 stop
DL
DL
$ 271

Chicago — Lexington

11:17—17:20
16 Sep 2026
5 h 3 m
1 stop
DL
DL
$ 271

Chicago — Lexington

13:55—21:16
16 Sep 2026
6 h 21 m
1 stop
DL
DL
$ 271

Chicago — Lexington

06:40—11:44
22 Sep 2026
4 h 4 m
1 stop
DL
DL
$ 271

Chicago — Lexington

06:05—11:44
22 Sep 2026
4 h 39 m
1 stop
DL
DL
$ 271

Chicago — Lexington

11:17—17:20
22 Sep 2026
5 h 3 m
1 stop
DL
DL
$ 271

Chicago — Lexington

10:48—17:10
22 Sep 2026
5 h 22 m
1 stop
DL
DL
$ 271

Chicago — Lexington

13:00—19:42
22 Sep 2026
5 h 42 m
1 stop
DL
DL
$ 271

Chicago — Lexington

08:05—14:46
22 Sep 2026
5 h 41 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — Lexington flight

Looking for cheap flights from Chicago to Lexington? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Lexington ticket online at the best price.

The route has direct flights — around 115 flights per week, flights are operated by United Airlines, American Airlines, British Airways, Air Canada, a nonstop flight takes about 1 h 25 min, the distance between the cities is around 502 km.

Planning your trip? You may find our Lexington travel guide, how to get from the airport into town and Lexington weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $218Min. price
OctoberCheapest
AugustPeak season
YesDirect flights
502 kmDistance
1 h 25 minTravel time
4Airlines
115 / wkFlights

Flight schedule from Chicago to Lexington

The table shows direct flights from Chicago to Lexington on the selected date. The flight takes approximately 1 h 25 min. Regular flights are operated by United Airlines, American Airlines, British Airways and Air Canada. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Blue Grass Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 25 Aug 2026

Flight ticket prices by day: Chicago — Lexington

Below is a calendar of the lowest flight ticket prices for Chicago — Lexington by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $218 in October, and the most expensive are around $371 in August. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Chicago to Lexington by month. Tickets are usually cheapest in May (around $194) and priciest in January (about $262) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$262highMay$194lowSep$194low
Feb$257highJun$222mediumOct$205medium
Mar$216mediumJul$234highNov$216medium
Apr$245highAug$222mediumDec$199low

Some values are estimated based on seasonality.

When to fly

Weather in Lexington: it is warmest in July (up to 30 °C on average) and coolest in January (around 6 °C). The driest month is September.

Tickets are usually cheapest in October and most expensive in August. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Lexington

Dry and wet days · Lexington

Wind speed and direction · Lexington

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How to get the best deal on a Chicago — Lexington ticket

  • Book ahead: fares for Chicago — Lexington are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Lexington is usually October — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — Lexington route are operated by 4 airlines; United Airlines runs the most flights (around 67% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    26x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → LEX26x/week
      Duration
      1h 39m
      Days
      MTWTFSS
    67.0%Open →
  • American AirlinesAA
    11x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → LEX11x/week
      Duration
      1h 29m
      Days
      MTWTFSS
    28.7%Open →
  • British AirwaysBA
    1x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight ORD → LEX1x/week
    3.5%Open →
  • Air CanadaAC
    1x/week
    WebsiteFleet: 20346M pax/year
    • Direct flight ORD → LEX1x/week
    0.9%Open →

Cities and airports on the Chicago — Lexington route

Flights Chicago — Lexington depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Blue Grass Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Lexington

LEX
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — Lexington flight

How long is the flight from Chicago to Lexington?

A nonstop Chicago — Lexington flight takes about 1 h 25 min — the distance between the cities is around 502 km.

How far is it from Chicago to Lexington?

The distance from Chicago to Lexington is about 502 km, which a nonstop flight covers in around 1 h 25 min.

Are there direct flights from Chicago to Lexington?

Yes, there are nonstop flights Chicago — Lexington — around 115 flights per week.

Which airlines fly from Chicago to Lexington?

Airlines operating Chicago — Lexington include United Airlines, American Airlines, British Airways, Air Canada. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Lexington flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Blue Grass Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Lexington?

The price of a Chicago — Lexington ticket depends on your travel date, season and demand: it is usually cheapest to fly in October, and most expensive in August. Tickets typically cost between $218 and $371. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Lexington?

Flights Chicago — Lexington are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is October. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Lexington?

To catch a low fare Chicago — Lexington, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually October.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from Lexington

See all
CharlotteAtlantaDallasDetroitPhiladelphiaNew York CityWashington, D.C.DenverMinneapolisTampaOrlandoSouth BendHuntsvilleGreensboroLansingPeoriaMorgantownRoanokeBirminghamAkronManhattanKalamazooHartfordWilmingtonCharlottesvilleGrand RapidsAugustaSyracuseJacksonMobileCedar RapidsAppletonMuskegonTorontoMontgomeryTallahasseePensacolaRochesterLynchburg

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