What is the cheapest airline that flies from Lexington Blue Grass to Chicago?

American Airlines and Delta are the most popular carriers operating from Lexington Blue Grass to Chicago

How many flights depart from Lexington to Chicago on average per day?

The number of flights available between Lexington and Chicago is 17 per day as of January 2026. The most frequent departure time is 8:00AM, with 57% of daily flights leaving in the afternoon.

What airlines fly to Chicago?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Lexington according to our data. American Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Lexington to Chicago on average per week?

The number of flights available between Lexington and Chicago is 124 per week as of January 2026. The most frequent departure day is Thu, with 19% of weekly flights leaving on this day.

When did momondo last update prices for flights from Lexington Blue Grass Airport to Chicago?

Prices for flights from Lexington Blue Grass Airport to Chicago are updated daily.

How many operators does momondo search for flights from Lexington Blue Grass Airport to Chicago?

The number of operators available for flights from Lexington Blue Grass Airport to Chicago is 2 as of January 2026.

How old do you have to be to fly from Lexington Blue Grass Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Lexington Blue Grass Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$118 Cheap Flights from Lexington to Chicago in 2026

Q: What is the typical price of a round-trip flight between Lexington and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $224 to $331. The lowest price recently found on this route was $189.

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Find the cheapest flights from Lexington to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:39 pm - 6:25 pm

LEX

ORD

1h 46mnonstop

9:20 pm - 11:44 pm

ORD

LEX

1h 24mnonstop

$189United Airlines

Sat, Mar 14 - Fri, Mar 20

4:59 pm - 5:39 pm

LEX

ORD

1h 40mnonstop

7:04 am - 9:28 am

ORD

LEX

1h 24mnonstop

$191American Airlines

Sat, Feb 21 - Sun, Feb 22

5:50 pm - 6:23 pm

LEX

ORD

1h 33mnonstop

2:24 pm - 4:55 pm

ORD

LEX

1h 31mnonstop

$197United Airlines

Tue, Jul 21 - Sat, Jul 25

4:27 pm - 5:12 pm

LEX

ORD

1h 45mnonstop

8:51 pm - 11:24 pm

ORD

LEX

1h 33mnonstop

$204American Airlines

Fri, Apr 24 - Mon, Apr 27

8:00 am - 8:47 am

LEX

ORD

1h 47mnonstop

8:51 pm - 11:24 pm

ORD

LEX

1h 33mnonstop

$206American Airlines

Sat, Apr 18 - Mon, Apr 20

7:30 am - 12:43 pm

LEX

MDW

6h 13m

1 stop

6:00 am - 1:34 pm

MDW

LEX

6h 34m

1 stop

$209Delta

Thu, Apr 16 - Mon, Apr 20

7:30 am - 10:09 am

LEX

ORD

3h 39m

1 stop

8:15 am - 1:34 pm

ORD

LEX

4h 19m

1 stop

$209Delta

Thu, Apr 16 - Mon, Apr 20

10:27 am - 11:02 am

LEX

ORD

1h 35mnonstop

7:04 am - 9:28 am

ORD

LEX

1h 24mnonstop

$219American Airlines

Thu, Feb 12 - Mon, Feb 16

9:26 pm - 9:04 am

LEX

RFD

12h 38m

1 stop

5:54 pm - 11:06 am

RFD

LEX

16h 12m

1 stop

$482Allegiant Air

Fri, Mar 6 - Sun, Mar 8

9:03 am - 5:03 pm

LEX

RFD

9h 00m

1 stop

5:42 pm - 2:54 pm

RFD

LEX

20h 12m

1 stop

$533Allegiant Air

Mon, Mar 30 - Sun, Apr 5

United Airlines flights from Lexington to Chicago

Our best United Airlines deals on Lexington to Chicago flight tickets

United Airlines

Mar 14

LEX5:39 pmLexington Blue Grass

1h 46m

ORD6:25 pmChicago O'Hare Intl

Mar 20

ORD9:20 pmChicago O'Hare Intl

1h 24m

LEX11:44 pmLexington Blue Grass

$189

United Airlines

Jul 21

LEX5:50 pmLexington Blue Grass

1h 33m

ORD6:23 pmChicago O'Hare Intl

Jul 25

ORD2:24 pmChicago O'Hare Intl

1h 31m

LEX4:55 pmLexington Blue Grass

$197

United Airlines

Apr 3

LEX5:45 pmLexington Blue Grass

1h 49m

ORD6:34 pmChicago O'Hare Intl

Apr 25

ORD5:55 pmChicago O'Hare Intl

1h 29m

LEX8:24 pmLexington Blue Grass

$263

Delta flights from Lexington to Chicago

Our best Delta deals on Lexington to Chicago flight tickets

Delta

Apr 16

LEX7:30 amLexington Blue Grass

3h 39m

1 stop

ORD10:09 amChicago O'Hare Intl

Apr 20

ORD8:15 amChicago O'Hare Intl

4h 19m

1 stop

LEX1:34 pmLexington Blue Grass

$209

Delta

Mar 30

LEX5:49 pmLexington Blue Grass

3h 28m

1 stop

ORD8:17 pmChicago O'Hare Intl

Apr 6

ORD9:50 amChicago O'Hare Intl

6h 17m

1 stop

LEX5:07 pmLexington Blue Grass

$224

Delta

Feb 13

LEX5:35 pmLexington Blue Grass

4h 09m

1 stop

ORD8:44 pmChicago O'Hare Intl

Feb 17

ORD5:59 pmChicago O'Hare Intl

4h 49m

1 stop

LEX11:48 pmLexington Blue Grass

$239

Fly from

Fly to

Route

Depart

Return

Price

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 3/14

5:39 pm-6:25 pm

Nonstop1h 46m

Chicago O'Hare Intl

Fri 3/20

9:20 pm-11:44 pm

Nonstop1h 24m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 2/21

4:59 pm-5:39 pm

Nonstop1h 40m

Chicago O'Hare Intl

Sun 2/22

7:04 am-9:28 am

Nonstop1h 24m

$191

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Tue 7/21

5:50 pm-6:23 pm

Nonstop1h 33m

Chicago O'Hare Intl

Sat 7/25

2:24 pm-4:55 pm

Nonstop1h 31m

$197

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Fri 4/24

4:27 pm-5:12 pm

Nonstop1h 45m

Chicago O'Hare Intl

Mon 4/27

8:51 pm-11:24 pm

Nonstop1h 33m

$204

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Sat 4/18

8:00 am-8:47 am

Nonstop1h 47m

Chicago O'Hare Intl

Mon 4/20

8:51 pm-11:24 pm

Nonstop1h 33m

$206

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Thu 4/16

7:30 am-12:43 pm

1 stop6h 13m

Chicago Midway

Mon 4/20

6:00 am-1:34 pm

1 stop6h 34m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 4/16

7:30 am-10:09 am

1 stop3h 39m

Chicago O'Hare Intl

Mon 4/20

8:15 am-1:34 pm

1 stop4h 19m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

Thu 2/12

10:27 am-11:02 am

Nonstop1h 35m

Chicago O'Hare Intl

Mon 2/16

7:04 am-9:28 am

Nonstop1h 24m

$219

LexingtonChicago

LEX - RFD

LEXRFD

Lexington Blue Grass

Fri 3/6

9:26 pm-9:04 am

1 stop12h 38m

Chicago Greater Rockford

Sun 3/8

5:54 pm-11:06 am

1 stop16h 12m

$482

LexingtonChicago

LEX - RFD

LEXRFD

Lexington Blue Grass

Mon 3/30

9:03 am-5:03 pm

1 stop9h 00m

Chicago Greater Rockford

Sun 4/5

5:42 pm-2:54 pm

1 stop20h 12m

$533

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Lexington to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Lexington and Chicago?

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Lexington, with most prices found around $245. If you’re not able to fly to Chicago in May, then October is your next best option. Flight prices from Lexington to Chicago during October average around $249.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $456. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Lexington to Chicago for around $746.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Lexington to Chicago during this time can be as low as $481. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $812.

What is the cheapest Lexington Blue Grass to Chicago flight route?

Fly from Lexington Blue Grass to Chicago O'Hare Intl for the best Lexington Blue Grass - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Lexington when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $279 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Lexington for as low as $189 on momondo.

What cabin class options are available on Lexington Blue Grass to Chicago flights?

There are 4 cabin classes available to choose from on Lexington Blue Grass to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Lexington to Chicago flights?

No. A direct flight is the cheapest option for a flight between Lexington to Chicago.

How have Lexington to Chicago flight prices changed over time?

As of January 2026, prices for Lexington to Chicago flights are approximately 2% cheaper when compared to flights at the same time last year.

When to book flights from Lexington to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Lexington to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Lexington to Chicago (LEX to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Lexington to Chicago

Best Price Found	$320
Fastest flight time	1h 33m
Direct flights	Mon, Wed, Thu, Fri, Sat and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Lexington in the past 72 hours is $320. The best round-trip flight deal from Lexington to Chicago found on momondo in the last 72 hours is $366.

The fastest flight from Lexington to Chicago takes 1h 33m

Direct flights go from Lexington to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.

There are 3 airports in Chicago. From Lexington there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

How far is Lexington Blue Grass to Chicago by plane?
The distance between Lexington Blue Grass and Chicago is about 312.4 mi. 1h 33m is a normal flight duration for this route.
When did momondo last update prices for flights from Lexington Blue Grass Airport to Chicago?
Prices for flights from Lexington Blue Grass Airport to Chicago are updated daily.
How many operators does momondo search for flights from Lexington Blue Grass Airport to Chicago?
The number of operators available for flights from Lexington Blue Grass Airport to Chicago is 2 as of January 2026.
How old do you have to be to fly from Lexington Blue Grass Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Lexington Blue Grass Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Lexington to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Lexington to Chicago is Embraer 175 (Enhanced Winglets) (22.30% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet CRJ-550 (21.19%), Canadair (Bombardier) Regional Jet 700 (17.66%), and Embraer 170 (11.48%).
What is the most popular airline from Lexington to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Lexington to Chicago is American Airlines (54% of total bookings). The next most popular airline is United Airlines (46%).

Best airlines flying from Lexington to Chicago

Compare and see reviews for airlines that fly from Lexington to Chicago with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $189	Free Cancellation	Rating 7.4 9,214 reviews		Search United Airlines flights
American Airlines	PriceFrom $189	Free Cancellation	Rating 7.2 11,205 reviews		Search American Airlines flights

United Airlines Flights From Lexington to Chicago
United Airlines flies from Lexington to Chicago around 20 times per week, with 9,214 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Lexington to Chicago in the last 72 hours was $189 (round-trip), much lower than the average airfare cost of $271 for United Airlines flights on this route.
American Airlines Flights From Lexington to Chicago
The best American Airlines deal for Lexington to Chicago flight tickets found on momondo in the last 72 hours was $189, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $279 round-trip. American Airlines operates 4 flights out of Lexington into Chicago in an average week, so prices vary by time and availability. 11,205 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Lexington to Chicago?

Finding the right flight to Chicago from Lexington is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Lexington to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Lexington with this policy.

How can momondo help me find flights from Lexington to Chicago?

Once all potential Lexington to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Lexington to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Lexington. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Sat 2/28

Sat 3/7

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Cheap flights from Lexington to Chicago from $118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Lexington to Chicago departing on 3/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Lexington to Chicago

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Cheap last minute flights

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United Airlines flights from Lexington to Chicago

Our best United Airlines deals on Lexington to Chicago flight tickets

Delta flights from Lexington to Chicago

Our best Delta deals on Lexington to Chicago flight tickets

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Use the filters below to find and compare flights from Lexington to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Lexington to Chicago

What is the typical price of a round-trip flight between Lexington and Chicago?

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Lexington, with most prices found around $245. If you’re not able to fly to Chicago in May, then October is your next best option. Flight prices from Lexington to Chicago during October average around $249.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Lexington to Chicago during this time can be as low as $481. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $812.

What is the cheapest Lexington Blue Grass to Chicago flight route?

Fly from Lexington Blue Grass to Chicago O'Hare Intl for the best Lexington Blue Grass - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Lexington Blue Grass to Chicago flights?

There are 4 cabin classes available to choose from on Lexington Blue Grass to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Lexington to Chicago flights?

No. A direct flight is the cheapest option for a flight between Lexington to Chicago.

How have Lexington to Chicago flight prices changed over time?

As of January 2026, prices for Lexington to Chicago flights are approximately 2% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Lexington Blue Grass to Chicago?

American Airlines and Delta are the most popular carriers operating from Lexington Blue Grass to Chicago

What airlines fly to Chicago?

How many flights depart from Lexington to Chicago on average per day?

The number of flights available between Lexington and Chicago is 17 per day as of January 2026. The most frequent departure time is 8:00AM, with 57% of daily flights leaving in the afternoon.

How many flights depart from Lexington to Chicago on average per week?

The number of flights available between Lexington and Chicago is 124 per week as of January 2026. The most frequent departure day is Thu, with 19% of weekly flights leaving on this day.

When to book flights from Lexington to Chicago

Cheap Lexington to Chicago (LEX to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Lexington to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Lexington Blue Grass to Chicago by plane?

When did momondo last update prices for flights from Lexington Blue Grass Airport to Chicago?

How many operators does momondo search for flights from Lexington Blue Grass Airport to Chicago?

How old do you have to be to fly from Lexington Blue Grass Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Lexington to Chicago?

What is the most popular airline from Lexington to Chicago?

Best airlines flying from Lexington to Chicago

Compare and see reviews for airlines that fly from Lexington to Chicago with momondo

United Airlines Flights From Lexington to Chicago

American Airlines Flights From Lexington to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Lexington to Chicago?

Can I find flights from Lexington to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Lexington to Chicago?

I’m not ready to book a flight from Lexington to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago