CA $501 Cheap Flights from Lexington (LEX) to Chicago (CHI)

View CA $501 flight on Tue, Apr 21, 2026Opens in a new window

Popular airlines from Blue Grass Airport (LEX) to Chicago

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Cheap flights from Lexington (LEX) to Chicago (CHI)

Prices were available within the past 7 days and start at CA $501 for one-way flights and CA $389 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $389 Roundtrip, found 5 days ago
CA $389
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $389 found 5 days ago
American Airlines
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $402 Roundtrip, found 5 days ago
CA $402
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $402 found 5 days ago
American Airlines
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $416 Roundtrip, found 5 days ago
CA $416
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $416 found 5 days ago
Delta
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $444 Roundtrip, found 5 days ago
CA $444
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $444 found 5 days ago
American Airlines
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $448 Roundtrip, found 5 days ago
CA $448
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $448 found 5 days ago
American Airlines
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $462 Roundtrip, found 5 days ago
CA $462
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $462 found 5 days ago
Delta
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $486 Roundtrip, found 5 days ago
CA $486
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $486 found 5 days ago
American Airlines
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $486 Roundtrip, found 5 days ago
CA $486
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $486 found 5 days ago
Delta
Sat, Apr 18 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $490 Roundtrip, found 5 days ago
CA $490
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Apr 18 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $490 found 5 days ago
United
Wed, Apr 22 - Sat, Apr 25
LEX
Lexington
ORD
Chicago
CA $514 Roundtrip, found 5 days ago
CA $514
Roundtrip
found 5 days ago
Select United flight, departing Wed, Apr 22 from Lexington to Chicago, returning Sat, Apr 25, priced at CA $514 found 5 days ago

Frequently asked questions

How much is a flight from LEX to Chicago, IL (CHI-All Airports)?
Start packing your suitcase, because round-trip flights between LEX and Chicago, IL (CHI-All Airports) start from CA $389. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can rise quickly, so book now to score the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from LEX to Chicago, IL (CHI-All Airports)?
This varies between air carriers, as each one has its own set of terms and conditions. Visit the Customer Service Portal, where you'll find easy instructions on how to cancel your flight online.
How do I find cheap flights from Blue Grass Airport (LEX) to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Blue Grass Airport (LEX) to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Blue Grass Airport to Chicago, IL (CHI-All Airports)?
You can forget about a movie marathon on this flight — it's just 570 kilometers from Lexington to Illinois. Sit down, order some snacks and you'll be in Illinois in next to no time.
Which airlines fly direct from Blue Grass Airport to Chicago, IL (CHI-All Airports)?
United Airlines (UA) is the preferred choice for many travelers. It operates 95 flights between Blue Grass Airport (LEX) and Chicago, IL (CHI-All Airports) each month. Another carrier operating on this route is American Airlines (AA). You'll have 60 flights every month to take your pick of.
Are LEX to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally nab a bargain, with some of the cheapest fares from Blue Grass Airport to Chicago, IL (CHI-All Airports) emerging a few weeks before the date of departure. If you'd rather book ahead, Expedia compares and updates the best flight deals regularly — as early as 12 months in advance in some cases. It does depend on the carrier though, as not every airline releases prices so far in advance.

Travel information

Origin airport
Blue Grass
Destination airport
O'Hare Intl.
Roundtrip price
CA $388
Distance
517 km
*Available to Expedia members.