$132 Cheap Flights from Lexington (LEX) to Chicago (ORD)

View $132 flight on Fri, Aug 22, 2025Opens in a new window

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

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Cheap Flights from Lexington to Chicago (LEX-ORD)

Prices were available within the past 7 days and start at $132 for one-way flights and $189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Nov 6 - Tue, Nov 11
LEX
Lexington
ORD
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select American Airlines flight, departing Thu, Nov 6 from Lexington to Chicago, returning Tue, Nov 11, priced at $189 just found
United
Sat, Oct 11 - Mon, Oct 13
LEX
Lexington
ORD
Chicago
$194 Roundtrip, found 9 hours ago
$194
Roundtrip
found 9 hours ago
Select United flight, departing Sat, Oct 11 from Lexington to Chicago, returning Mon, Oct 13, priced at $194 found 9 hours ago
United
Thu, Nov 27 - Fri, Nov 28
LEX
Lexington
ORD
Chicago
$194 Roundtrip, found 3 hours ago
$194
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Nov 27 from Lexington to Chicago, returning Fri, Nov 28, priced at $194 found 3 hours ago
United
Thu, Jul 31 - Mon, Aug 4
LEX
Lexington
ORD
Chicago
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Select United flight, departing Thu, Jul 31 from Lexington to Chicago, returning Mon, Aug 4, priced at $198 found 3 days ago
United
Tue, Jul 22 - Tue, Jul 29
LEX
Lexington
ORD
Chicago
$199 Roundtrip, found 8 hours ago
$199
Roundtrip
found 8 hours ago
Select United flight, departing Tue, Jul 22 from Lexington to Chicago, returning Tue, Jul 29, priced at $199 found 8 hours ago
United
Thu, Jul 31 - Sun, Aug 3
LEX
Lexington
ORD
Chicago
$202 Roundtrip, found 11 hours ago
$202
Roundtrip
found 11 hours ago
Select United flight, departing Thu, Jul 31 from Lexington to Chicago, returning Sun, Aug 3, priced at $202 found 11 hours ago
American Airlines
Fri, Oct 3 - Tue, Oct 7
LEX
Lexington
ORD
Chicago
$202 Roundtrip, found 4 hours ago
$202
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Oct 3 from Lexington to Chicago, returning Tue, Oct 7, priced at $202 found 4 hours ago
United
Fri, Aug 1 - Tue, Aug 5
LEX
Lexington
ORD
Chicago
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select United flight, departing Fri, Aug 1 from Lexington to Chicago, returning Tue, Aug 5, priced at $206 found 1 day ago
United
Thu, Jul 24 - Thu, Jul 31
LEX
Lexington
ORD
Chicago
$207 Roundtrip, found 4 hours ago
$207
Roundtrip
found 4 hours ago
Select United flight, departing Thu, Jul 24 from Lexington to Chicago, returning Thu, Jul 31, priced at $207 found 4 hours ago
Delta
Wed, Sep 10 - Sat, Sep 20
LEX
Lexington
ORD
Chicago
$209 Roundtrip, found 1 hour ago
$209
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Sep 10 from Lexington to Chicago, returning Sat, Sep 20, priced at $209 found 1 hour ago

Find the cheapest month to fly from Lexington (LEX) to Chicago (ORD)

November is typically the cheapest month to fly

From $123 - $385 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $294
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $294
0
Flights from Lexington (LEX) to Chicago (ORD)
Origin airport
Blue Grass
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$189
Distance
323 mi

Lexington to Chicago Flights

The cheapest times to fly from Lexington to Chicago

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 Lexington to Chicago are during the month of November. You can find some of the cheapest flights from Lexington to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Lexington to Chicago

Sunday is one of the best days to book for cheap flights from Lexington to Chicago: 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 Lexington to Chicago

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 Lexington to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $132 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 Lexington to Chicago 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 Lexington to Chicago 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.

 

Frequently asked questions

How much does a flight from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD) cost?
You'll find cheap return flights from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD) starting at $189. Snag a seat and be on your way. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving LEX on July 29 2025 and touching down at ORD. The price was last updated on July 3 2025 and has not changed since.
What is the cheapest month to fly from LEX to ORD?
The cheapest flights from LEX to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD)?
When flying out of Blue Grass Airport (LEX), you can get on a nonstop flight to O'Hare Intl. Airport (ORD) with United Airlines.
What is the cheapest airline that flies from LEX to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from LEX to ORD. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD)?
When departing from Blue Grass Airport (LEX), you can take your pick from an average of 4 daily nonstop flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD)?
Flights between LEX and ORD are their busiest at 2 PM. For a more relaxed experience and potentially cheaper prices, choose a departure that's outside typical rush times.
What day of the week has the most flights from LEX to ORD?
Jet off on a Wednesday if you're searching for the best choice of flights from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD)?
The first flight of the day departing from Blue Grass Airport (LEX) is at around 6:50AM UTC-5. Catch this flight and you'll touch down at O'Hare Intl. Airport (ORD) at approximately 7:26AM UTC-6. The total travel time is 1h 36m.
How long does it take to fly from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD)?
Flights from LEX to ORD have an average travel time of 1 hour and 44 minutes. The distance between the two is 320 mi.
What is the best time to fly from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD) route, travel before 3 PM. Flights after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Blue Grass Airport (LEX)?
If you're traveling on a direct flight from Blue Grass Airport (LEX) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book a flight from LEX to ORD often results in higher prices. While you might find some last-minute deals, they're not always guaranteed. Keep your travel schedule open for a better chance of scoring a bargain.
Is it cheaper to book a LEX to ORD flight and hotel package?
You'll typically save money by securing a LEX to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've selected your ideal flights and accommodations, consider adding extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from Blue Grass Airport (LEX) to O'Hare Intl. Airport (ORD)?
It's generally possible to reschedule or cancel your LEX to ORD flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

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