$108 Cheap Flights from Lexington (LEX) to Chicago (ORD)

View $108 flight on Wed, Jul 16, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Lexington to Chicago (LEX-ORD)

Prices were available within the past 7 days and start at $108 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
Fri, May 16 - Sun, May 18
LEX
Lexington
ORD
Chicago
$189 Roundtrip, just found
$189
Roundtrip
just found
Select American Airlines flight, departing Fri, May 16 from Lexington to Chicago, returning Sun, May 18, priced at $189 just found
United
Thu, May 22 - Sat, May 24
LEX
Lexington
ORD
Chicago
$191 Roundtrip, found 9 hours ago
$191
Roundtrip
found 9 hours ago
Select United flight, departing Thu, May 22 from Lexington to Chicago, returning Sat, May 24, priced at $191 found 9 hours ago
United
Wed, May 7 - Wed, May 14
LEX
Lexington
ORD
Chicago
$194 Roundtrip, found 1 hour ago
$194
Roundtrip
found 1 hour ago
Select United flight, departing Wed, May 7 from Lexington to Chicago, returning Wed, May 14, priced at $194 found 1 hour ago
American Airlines
Fri, May 9 - Mon, May 12
LEX
Lexington
ORD
Chicago
$199 Roundtrip, found 3 hours ago
$199
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Fri, May 9 from Lexington to Chicago, returning Mon, May 12, priced at $199 found 3 hours ago
American Airlines
Wed, Jul 16 - Sat, Jul 19
LEX
Lexington
ORD
Chicago
$202 Roundtrip, found 2 hours ago
$202
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Jul 16 from Lexington to Chicago, returning Sat, Jul 19, priced at $202 found 2 hours ago
United
Fri, Aug 8 - Sun, Aug 10
LEX
Lexington
ORD
Chicago
$204 Roundtrip, found 2 hours ago
$204
Roundtrip
found 2 hours ago
Select United flight, departing Fri, Aug 8 from Lexington to Chicago, returning Sun, Aug 10, priced at $204 found 2 hours ago
United
Fri, Aug 8 - Sun, Aug 10
LEX
Lexington
ORD
Chicago
$206 Roundtrip, found 2 hours ago
$206
Roundtrip
found 2 hours ago
Select United flight, departing Fri, Aug 8 from Lexington to Chicago, returning Sun, Aug 10, priced at $206 found 2 hours ago
Delta
Fri, May 30 - Tue, Jun 3
LEX
Lexington
ORD
Chicago
$209 Roundtrip, found 1 hour ago
$209
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, May 30 from Lexington to Chicago, returning Tue, Jun 3, priced at $209 found 1 hour ago
United
Tue, Jul 8 - Sat, Jul 19
LEX
Lexington
ORD
Chicago
$209 Roundtrip, found 5 hours ago
$209
Roundtrip
found 5 hours ago
Select United flight, departing Tue, Jul 8 from Lexington to Chicago, returning Sat, Jul 19, priced at $209 found 5 hours ago
United
Sat, Jul 12 - Wed, Jul 16
LEX
Lexington
ORD
Chicago
$211 Roundtrip, found 5 days ago
$211
Roundtrip
found 5 days ago
Select United flight, departing Sat, Jul 12 from Lexington to Chicago, returning Wed, Jul 16, priced at $211 found 5 days ago

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 May 13 2025 and touching down at ORD. The price was last updated on April 22 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?
Currently, the cheapest carrier operating one-way flights from LEX to ORD is American Airlines. You can book a seat on this route from $214. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from LEX on July 15 2025. Prices were last updated on April 22 2025 and have not changed since.
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.
*Available to One Key members.