- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Flights from Lexington, KY to Chicago, IL depart on average 37 times per day, taking around 4h 14m. Cheap flight tickets for this journey start at €213 but you can travel from only €58 by bus.
There are 7 flights per day. The earliest flight runs at 00:02, the last at 23:03. The fastest flight covers the 315 miles (507 km) distance in 1h 39m. May is the cheapest month to fly.
Distance 315 miles (507 km) |
Average flight duration 4h 14m |
Cheapest ticket price €213 |
Flights per day 37 |
Direct flights 7 |
Fastest flight 1h 39m |
First flight 12:02 AM |
Last flight 11:03 PM |
Cheapest Month May |
Cheapest Day Wed |
High Season Jul - Sep |
Low Season Jan - Mar |
Cheapest price on Sep 21
€336
Average ticket price on Sep 21
€484
Fastest journey on Sep 21
1 h 44 m
Average journey duration on Sep 21
1 h 46 m
Flights on Sep 21
38
Distance
507 km
The best way to find a cheap flight ticket from Lexington, KY to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Lexington, KY to Chicago, IL will cost around €484 if you buy it on the day, but the cheapest tickets can be found for only €336.
On Mon, Sep 21, we found 38 flights from Lexington, KY to Chicago, IL, including 7 direct services.
On Mon, Sep 21 the direct flights cover the 507 km distance in an average of 1 h 46 m but if you time it right, some flights will get you there in just 1 h 44 m .
On Mon, Sep 21 the longest flights will take 1 h 48 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
AA5014
UA5871
AA5012
UA5443
UA5344
UA5443
UA5344
AA5012
AA6307
UA5445Omio recommends booking the flight as it is the most popular option from Lexington, KY to Chicago, IL among Omio's users. If you are prioritising price, take the bus, with an average ticket price of €92 For those with little time, consider booking a flight, which has an average total journey time of 6h 14m. Average ticket prices depend on the travel mode: a bus costs an average of €92, while a flight costs an average of €360.
Distance: 315 miles (507 km)
Most popular Flight | Bus | Driving |
|---|---|---|
€360 Average price | €92 Average price Cheapest | €29 Average price (fuel + tolls) |
6h 14m Average total duration Fastest 4h 14m Onboard + 2h 0m Additional time* | 12h 20m Average total duration 11h 50m Onboard + 30m Additional time* | 5h 46m Average total duration (door-to-door) |
![]() Most popular airline | ![]() Most popular bus company | Your own car or car rental |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Lexington, KY to Chicago, IL:
A bus is €268 less than a flight for this route with tickets for a flight from Lexington, KY to Chicago, IL costing on average €360.
Other travel options to Chicago, IL take longer:
Bus takes on average 11h 50m.
The table below shows live departures for Lexington, KY to Chicago, IL flights for today, Sunday, September 20. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
AA2155+ AA5257 | 4:48 PM Blue Grass Airport | 6h47 | 10:35 PM O'Hare International Airport | 1 transfer | |
AA490+ AA5257 | 4:48 PM Blue Grass Airport | 5h42 | 9:30 PM O'Hare International Airport | 1 transfer | |
AA2668+ AA5257 | 4:48 PM Blue Grass Airport | 8h08 | 11:56 PM O'Hare International Airport | 1 transfer | |
AA1620+ AA3927 | 5:43 PM Blue Grass Airport | 7h31 | 12:14 AM O'Hare International Airport | 1 transfer | |
AA2346+ AA3927 | 5:43 PM Blue Grass Airport | 6h47 | 11:30 PM O'Hare International Airport | 1 transfer | |
UA5871 | 5:57 PM Blue Grass Airport | 1h52 | 6:49 PM O'Hare International Airport | 0 transfersDirect | |
AA815+ AA5574 | 5:59 PM Blue Grass Airport | 5h32 | 10:31 PM O'Hare International Airport | 1 transfer | |
AA627+ AA5574 | 5:59 PM Blue Grass Airport | 7h00 | 11:59 PM O'Hare International Airport | 1 transfer | |
AA5014 | 6:01 PM Blue Grass Airport | 1h58 | 6:59 PM O'Hare International Airport | 0 transfersDirect | |
AA627+ AA5258 | 8:13 PM Blue Grass Airport | 4h46 | 11:59 PM O'Hare International Airport | 1 transfer | |
AA6307 | 5:23 AM Blue Grass Airport | 1h47 | 6:10 AM O'Hare International Airport | 0 transfersDirect | |
AA328+ AA5198 | 6:00 AM Blue Grass Airport | 6h09 | 11:09 AM O'Hare International Airport | 1 transfer | |
AA2908+ AA5278 | 6:00 AM Blue Grass Airport | 7h14 | 12:14 PM O'Hare International Airport | 1 transfer | |
AA1038+ AA5278 | 6:00 AM Blue Grass Airport | 5h45 | 10:45 AM O'Hare International Airport | 1 transfer | |
UA5344 | 7:00 AM Blue Grass Airport | 1h45 | 7:45 AM O'Hare International Airport | 0 transfersDirect | |
AA821+ AA5577 | 7:27 AM Blue Grass Airport | 9h43 | 4:10 PM O'Hare International Airport | 1 transfer | |
AA865+ AA5577 | 7:27 AM Blue Grass Airport | 5h49 | 12:16 PM O'Hare International Airport | 1 transfer | |
AA1854+ AA5577 | 7:27 AM Blue Grass Airport | 7h42 | 2:09 PM O'Hare International Airport | 1 transfer | |
AA2530+ AA5345 | 7:36 AM Blue Grass Airport | 7h44 | 2:20 PM O'Hare International Airport | 1 transfer | |
AA2908+ AA5345 | 7:36 AM Blue Grass Airport | 5h38 | 12:14 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA1131 | 9:15 AM Blue Grass Airport | 12h06 | 8:21 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA675 | 9:15 AM Blue Grass Airport | 10h17 | 6:32 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA617 | 9:15 AM Blue Grass Airport | 8h50 | 5:05 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA2865 | 9:15 AM Blue Grass Airport | 6h45 | 3:00 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA2258 | 9:15 AM Blue Grass Airport | 14h31 | 10:46 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA1050 | 9:15 AM Blue Grass Airport | 11h25 | 7:40 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA377 | 9:15 AM Blue Grass Airport | 15h44 | 11:59 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA1055 | 9:15 AM Blue Grass Airport | 13h44 | 9:59 PM O'Hare International Airport | 1 transfer | |
UA1808 · UA2272 | 9:15 AM Blue Grass Airport | 13h15 | 9:30 PM O'Hare International Airport | 1 transfer | |
UA5445 | 9:50 AM Blue Grass Airport | 1h48 | 10:38 AM O'Hare International Airport | 0 transfersDirect | |
AA5012 | 11:13 AM Blue Grass Airport | 1h46 | 11:59 AM O'Hare International Airport | 0 transfersDirect | |
AA536+ AA5572 | 11:43 AM Blue Grass Airport | 6h55 | 5:38 PM O'Hare International Airport | 1 transfer | |
AA2423+ AA5572 | 11:43 AM Blue Grass Airport | 5h17 | 4:00 PM O'Hare International Airport | 1 transfer | |
AA2488+ AA5572 | 11:43 AM Blue Grass Airport | 8h55 | 7:38 PM O'Hare International Airport | 1 transfer | |
AA2656+ AA5024 | 1:36 PM Blue Grass Airport | 8h33 | 9:09 PM O'Hare International Airport | 1 transfer | |
AA2257+ AA5024 | 1:36 PM Blue Grass Airport | 7h54 | 8:30 PM O'Hare International Airport | 1 transfer | |
UA5443 | 1:57 PM Blue Grass Airport | 1h44 | 2:41 PM O'Hare International Airport | 0 transfersDirect | |
AA2488+ AA5015 | 3:10 PM Blue Grass Airport | 5h28 | 7:38 PM O'Hare International Airport | 1 transfer | |
AA815+ AA5015 | 3:10 PM Blue Grass Airport | 8h21 | 10:31 PM O'Hare International Airport | 1 transfer | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare bus and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
Find answers to the most common questions about traveling from Lexington, KY to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Most Lexington, KY to Chicago, IL flights use the Blue Grass Airport to O'Hare International Airport airport pair. Use this guide to compare Lexington, KY and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Blue Grass Airport is 12 km from Lexington city centre. Public transport options include:
Blue Grass Airport has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food options include: Several dining options available in terminals.
Free Wi-Fi available throughout the airport. ATMs are aTMs available near baggage claim and main terminal.
Ticket office support is available at Blue Grass Airport.
Available at Blue Grass Airport: Parking, Taxis, WC.
Accessibility facilities are available at Blue Grass Airport: Fully accessible for individuals with disabilities.
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Here are some other resources that might have the information you need