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Cheap flights from Lexington to Chicago from $107

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 1/8. 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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0 bags

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Find the cheapest flights from Lexington to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
5:32 pm - 6:29 pm
LEX
-
ORD
1h 57mnonstop
United Airlines Logo
2:15 pm - 4:48 pm
ORD
-
LEX
1h 33mnonstop
$189United Airlines
vie., ene. 30 - lun., feb. 2
American Airlines Logo
10:13 pm - 10:56 pm
LEX
-
ORD
1h 43mnonstop
American Airlines Logo
8:54 pm - 11:23 pm
ORD
-
LEX
1h 29mnonstop
$204American Airlines
dom., ene. 4 - dom., ene. 18
Delta Logo
6:00 am - 9:53 am
LEX
-
MDW
4h 53m1 stop
Delta Logo
12:48 pm - 5:51 pm
MDW
-
LEX
4h 03m1 stop
$209Delta
jue., ene. 29 - lun., feb. 2
Delta Logo
10:39 am - 1:08 pm
LEX
-
ORD
3h 29m1 stop
Delta Logo
10:35 am - 4:55 pm
ORD
-
LEX
5h 20m1 stop
$209Delta
lun., ene. 5 - jue., ene. 22
United Airlines Logo
5:48 pm - 6:43 pm
LEX
-
ORD
1h 55mnonstop
United Airlines Logo
2:33 pm - 5:05 pm
ORD
-
LEX
1h 32mnonstop
$215United Airlines
mié., dic. 24 - jue., dic. 25
United Airlines Logo
6:00 am - 6:55 am
LEX
-
ORD
1h 55mnonstop
United Airlines Logo
6:20 pm - 9:04 pm
ORD
-
LEX
1h 44mnonstop
$219United Airlines
lun., dic. 22 - vie., dic. 26
American Airlines Logo
5:02 pm - 5:43 pm
LEX
-
ORD
1h 41mnonstop
American Airlines Logo
8:54 pm - 11:14 pm
ORD
-
LEX
1h 20mnonstop
$222American Airlines
vie., feb. 13 - dom., feb. 15
American Airlines Logo
4:58 pm - 5:49 pm
LEX
-
ORD
1h 51mnonstop
American Airlines Logo
3:21 pm - 11:15 pm
ORD
-
LEX
6h 54m1 stop
$232American Airlines
vie., ene. 30 - lun., feb. 2
Allegiant Air Logo
9:26 pm - 9:04 am
LEX
-
RFD
12h 38m1 stop
Allegiant Air Logo
5:54 pm - 11:06 am
RFD
-
LEX
16h 12m1 stop
$321Allegiant Air
vie., mar. 6 - dom., mar. 8
Allegiant Air Logo
9:09 am - 5:45 pm
LEX
-
RFD
9h 36m1 stop
Allegiant Air Logo
7:59 pm - 3:50 pm
RFD
-
LEX
18h 51m1 stop
$434Allegiant Air
vie., dic. 19 - sáb., dic. 20

American Airlines flights from Lexington to Chicago

Our best American Airlines deals on Lexington to Chicago flight tickets
American Airlines
Jan 4
LEX10:13 pmLexington Blue Grass
1h 43m
ORD10:56 pmChicago O'Hare Intl
Jan 18
ORD8:54 pmChicago O'Hare Intl
1h 29m
LEX11:23 pmLexington Blue Grass
$204
Find similar
American Airlines
Feb 13
LEX5:02 pmLexington Blue Grass
1h 41m
ORD5:43 pmChicago O'Hare Intl
Feb 15
ORD8:54 pmChicago O'Hare Intl
1h 20m
LEX11:14 pmLexington Blue Grass
$222
Find similar
American Airlines
Jan 30
LEX4:58 pmLexington Blue Grass
1h 51m
ORD5:49 pmChicago O'Hare Intl
Feb 2
ORD3:21 pmChicago O'Hare Intl
6h 54m
1 stop
LEX11:15 pmLexington Blue Grass
$232
Find similar

United Airlines flights from Lexington to Chicago

Our best United Airlines deals on Lexington to Chicago flight tickets
United Airlines
Jan 30
LEX5:32 pmLexington Blue Grass
1h 57m
ORD6:29 pmChicago O'Hare Intl
Feb 2
ORD2:15 pmChicago O'Hare Intl
1h 33m
LEX4:48 pmLexington Blue Grass
$189
Find similar
United Airlines
Jun 6
LEX5:50 pmLexington Blue Grass
1h 33m
ORD6:23 pmChicago O'Hare Intl
Jun 8
ORD6:00 pmChicago O'Hare Intl
1h 23m
LEX8:23 pmLexington Blue Grass
$203
Find similar
United Airlines
Dec 24
LEX5:48 pmLexington Blue Grass
1h 55m
ORD6:43 pmChicago O'Hare Intl
Dec 25
ORD2:33 pmChicago O'Hare Intl
1h 32m
LEX5:05 pmLexington Blue Grass
$215
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Lexington to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated diciembre 8, 2025.
Use the filters below to find and compare flights from Lexington to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

vie. 1/30

5:32 pm-6:29 pm

Nonstop1h 57m

Chicago O'Hare Intl

lun. 2/2

2:15 pm-4:48 pm

Nonstop1h 33m

$189

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

dom. 1/4

10:13 pm-10:56 pm

Nonstop1h 43m

Chicago O'Hare Intl

dom. 1/18

8:54 pm-11:23 pm

Nonstop1h 29m

$204

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

jue. 1/29

6:00 am-9:53 am

1 stop4h 53m

Chicago Midway

lun. 2/2

12:48 pm-5:51 pm

1 stop4h 03m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

lun. 1/5

10:39 am-1:08 pm

1 stop3h 29m

Chicago O'Hare Intl

jue. 1/22

10:35 am-4:55 pm

1 stop5h 20m

$209

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

mié. 12/24

5:48 pm-6:43 pm

Nonstop1h 55m

Chicago O'Hare Intl

jue. 12/25

2:33 pm-5:05 pm

Nonstop1h 32m

$215

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

lun. 12/22

6:00 am-6:55 am

Nonstop1h 55m

Chicago O'Hare Intl

vie. 12/26

6:20 pm-9:04 pm

Nonstop1h 44m

$219

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

vie. 2/13

5:02 pm-5:43 pm

Nonstop1h 41m

Chicago O'Hare Intl

dom. 2/15

8:54 pm-11:14 pm

Nonstop1h 20m

$222

LexingtonChicago

LEX - ORD

LEXORD

Lexington Blue Grass

vie. 1/30

4:58 pm-5:49 pm

Nonstop1h 51m

Chicago O'Hare Intl

lun. 2/2

3:21 pm-11:15 pm

1 stop6h 54m

$232

LexingtonChicago

LEX - RFD

LEXRFD

Lexington Blue Grass

vie. 3/6

9:26 pm-9:04 am

1 stop12h 38m

Chicago Greater Rockford

dom. 3/8

5:54 pm-11:06 am

1 stop16h 12m

$321

LexingtonChicago

LEX - RFD

LEXRFD

Lexington Blue Grass

vie. 12/19

9:09 am-5:45 pm

1 stop9h 36m

Chicago Greater Rockford

sáb. 12/20

7:59 pm-3:50 pm

1 stop18h 51m

$434

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 January is, on average, the cheapest month to fly to Chicago from Lexington, with most prices found around $236. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Lexington to Chicago during May average around $245.

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 $462. 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 $779.

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 evening. Flights from Lexington to Chicago during this time can be as low as $477. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $825.

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 $278 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 December 2025, prices for Lexington to Chicago flights are approximately 111% more expensive 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

$228

Fastest flight time

1h 33m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Lexington in the past 72 hours is $228. The best round-trip flight deal from Lexington to Chicago found on momondo in the last 72 hours is $329.
The fastest flight from Lexington to Chicago takes 1h 33m
Direct flights go from Lexington to Chicago every day.
There is 1 airport near Chicago: 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $189Free CancellationRating
7.4
9,089 reviews
Search United Airlines flights
American AirlinesPriceFrom $189Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights

  • United Airlines Flights From Lexington to Chicago

    United Airlines flies from Lexington to Chicago around 26 times per week, with 9,089 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 $276 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 $274 round-trip. American Airlines operates 18 flights out of Lexington into Chicago in an average week, so prices vary by time and availability. 11,045 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport