Beginning of main content

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Fares from $116 One Way, $244 Round Trip from Lexington to Chicago

Prices starting at $244 for return flights and $116 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Need A Hotel In Chicago?

Hotels In Top Chicago Neighborhoods

Near North Side
360 hotels

Loews Chicago Hotel

4.5 out of 5.0
from

$129

The Loop
232 hotels
from

$109

River North
201 hotels

ACME Hotel Company

3.5 out of 5.0
from

$78

Stay Near Exciting Chicago Attractions

More About Flying To Chicago from Lexington

Route Information for Flights from Lexington to Chicago

Origin Airport IATA CodeLEX
Destination Airport IATA CodeCHI
Distance323 mi
Direct Flight AirlinesAmerican Airlines, JAL, Alaska Airlines, ANA, Air New Zealand, United Airlines, British Airways
Earliest Flight Arrival12:59PM UTC
Latest Flight Arrival11:31PM UTC

Flights Review

Sep 22, 2019

I loved the very friendly and engaging pilot!!!!!!

Aug 26, 2019

Orbitz does not enter my TSA number with airlines when I book with you. That is an inconvenience.

Jun 26, 2019

There was a two-hour delay on the flight from New Orleans and no explanation was given by American Airlines personnel. That was an inconvenience to the person who hosted me for the night in Chicago, since I arrived at her place around midnight. Also it forced me to find a cab, since it was so late at night.

Oct 1, 2018

Those middle seats are not comfortable at all.

May 4, 2018

Weather was an issue, but I was easily rebooked the next day. It was inconvenient, sure, but not the fault of American. They made the situation very tolerable.

Fly from Lexington to Chicago

Lexington's Airport Information

Orbitz.com can help you find flights from Lexington, Kentucky, by searching many airlines at once to find bargain tickets. The Blue Grass Airport serves Lexington and the surrounding areas. It is located at the intersection of US 60 and Man o'War Boulevard, four miles west of the city center. Seven airlines, including Allegiant, Eagle and Delta, provide scheduled domestic flights.

Airport Parking Information

The Blue Grass Airport has both short-term and long-term parking available. Fees are $2.00 for the first hour and $1.00 for each additional hour, with a daily maximum of $14.00 in the short-term lot and $11.00 per day in the long-term lots. There is an economy lot with a daily maximum of $8.00 per day. Any car with handicap plates or placards will be charged $8.00 per day, regardless of lot. Detailing service is available while you are traveling. Payment can be made with Visa, MasterCard, American Express or cash.

Ground Transportation Information

If you would prefer not to leave your car at the airport, metered taxis are available to transport you. Fares are approximately $2.50 per mile, with an initial $2.50 charge. There is also a bus stop at the airport. There is an express bus route from Blue Grass Airport to the downtown Transit Center on Vine Street, Monday through Friday, from 6 a.m. to 6 p.m. Let Orbitz.com help you plan your next trip. Not only can we find you great deals on an air ticket, we can find ground transportation too.

Blue Grass Airport Restaurants

There are several restaurant options available at the Blue Grass Airport. Market Fresh, Knob Creek Bourbon Lounge, The Taproom and Primo Cappuchino are all great places to grab a bite to eat while you are waiting for your flight. There are also several shops if you need to make any last minute purchases. Orbitz.com can help you find great deals on flights from Lexington.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Flights from Lexington to Chicago - Frequently Asked Questions

Are there non-stop flights from Lexington to Chicago?

Get set to pack your suitcase, because there are a couple of carriers that operate direct flights from Lexington, KY (LEX-Blue Grass) to Chicago, IL (ORD-O'Hare Intl.). You can book a seat with United Airlines and American Airlines.

What is the shortest flight from Lexington to Chicago?

The journey from Lexington to Chicago can be as quick as 1 hour and 22 minutes. With a short and sweet flight time like this, why not organize a spur-of-the-moment getaway?

What airlines fly from Lexington (and vicinity) to Chicago (and vicinity) most frequently?

United Airlines (UA) is one of the carriers with the most flights from Lexington, KY Airport (LEX-Blue Grass) to Chicago, IL Airport (ORD-OHare Intl.). It offers 101 flights on this route each month. Taking off on a vacation is one of life's biggest pleasures, and this airline will get you to your destination quickly and safely. If you need a few more options, look up the price of tickets with American Airlines (AA), which offers 69 flights from Lexington (and vicinity) to Chicago (and vicinity) each month.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.