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Cheap flights from Louisville to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Louisville to Chicago departing on 10/22. 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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Find the cheapest flights from Louisville to Chicago

Cheap round-trip flights

Southwest Logo
3:20 pm - 9:05 pmSDF-MDW
6h 45m1 stop
Southwest Logo
7:15 pm - 9:30 pmMDW-SDF
1h 15mnonstop
$107Southwest
Find Deal
mar., nov. 4 - jue., nov. 6
Southwest Logo
11:45 am - 8:30 pmSDF-MDW
9h 45m2 stops
Southwest Logo
7:15 pm - 9:30 pmMDW-SDF
1h 15mnonstop
$112Southwest
Find Deal
mar., nov. 4 - jue., nov. 6
American Airlines Logo
6:45 am - 7:18 amSDF-ORD
1h 33mnonstop
American Airlines Logo
8:21 pm - 10:56 pmORD-SDF
1h 35mnonstop
$134American Airlines
Find Deal
mar., oct. 14 - vie., oct. 17
United Airlines Logo
9:00 am - 9:40 amSDF-ORD
1h 40mnonstop
United Airlines Logo
7:30 am - 9:59 amORD-SDF
1h 29mnonstop
$152United Airlines
Find Deal
mar., nov. 4 - jue., nov. 6
United Airlines Logo
7:00 am - 7:38 amSDF-ORD
1h 38mnonstop
United Airlines Logo
4:00 pm - 6:33 pmORD-SDF
1h 33mnonstop
$157United Airlines
Find Deal
mar., oct. 7 - mar., oct. 14
American Airlines Logo
6:45 am - 7:18 amSDF-ORD
1h 33mnonstop
American Airlines Logo
8:28 pm - 11:03 pmORD-SDF
1h 35mnonstop
$164American Airlines
Find Deal
mar., oct. 14 - mar., oct. 21
Delta Logo
6:00 am - 10:19 amSDF-ORD
5h 19m1 stop
Delta Logo
6:22 pm - 11:57 pmORD-SDF
4h 35m1 stop
$177Delta
Find Deal
mié., nov. 12 - sáb., nov. 15
Delta Logo
6:00 am - 9:52 amSDF-MDW
4h 52m1 stop
Delta Logo
5:34 pm - 12:06 amMDW-SDF
5h 32m1 stop
$177Delta
Find Deal
mar., nov. 11 - mar., nov. 11
Logo
6:00 am - 9:12 amSDF-MDW
28h 12m1 stop
Logo
9:27 am - 11:45 pmMDW-SDF
13h 18m1 stop
$203
Find Deal
mié., nov. 12 - lun., nov. 17
Logo
7:15 am - 12:26 pmSDF-ORD
30h 11m1 stop
Logo
5:59 pm - 9:04 amORD-SDF
14h 05m1 stop
$208
Find Deal
jue., oct. 30 - jue., nov. 6

United Airlines flights from Louisville to Chicago

Our best United Airlines deals on Louisville to Chicago flight tickets
United Airlines
Nov 4
SDF9:00 amLouisville Intl
1h 40m
ORD9:40 amChicago O'Hare Intl
Nov 6
ORD7:30 amChicago O'Hare Intl
1h 29m
SDF9:59 amLouisville Intl
$152
Find similar
United Airlines
Oct 7
SDF7:00 amLouisville Intl
1h 38m
ORD7:38 amChicago O'Hare Intl
Oct 14
ORD4:00 pmChicago O'Hare Intl
1h 33m
SDF6:33 pmLouisville Intl
$157
Find similar
United Airlines
Oct 16
SDF7:20 pmLouisville Intl
1h 49m
ORD8:09 pmChicago O'Hare Intl
Oct 20
ORD7:50 pmChicago O'Hare Intl
1h 40m
SDF10:30 pmLouisville Intl
$159
Find similar

American Airlines flights from Louisville to Chicago

Our best American Airlines deals on Louisville to Chicago flight tickets
American Airlines
Oct 14
SDF6:45 amLouisville Intl
1h 33m
ORD7:18 amChicago O'Hare Intl
Oct 17
ORD8:21 pmChicago O'Hare Intl
1h 35m
SDF10:56 pmLouisville Intl
$134
Find similar
American Airlines
Oct 14
SDF6:45 amLouisville Intl
1h 33m
ORD7:18 amChicago O'Hare Intl
Oct 21
ORD8:28 pmChicago O'Hare Intl
1h 35m
SDF11:03 pmLouisville Intl
$164
Find similar
American Airlines
Oct 20
SDF6:45 amLouisville Intl
1h 33m
ORD7:18 amChicago O'Hare Intl
Oct 22
ORD9:45 amChicago O'Hare Intl
6h 58m
1 stop
SDF5:43 pmLouisville Intl
$174
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Louisville 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 septiembre 16, 2025.
Use the filters below to find and compare flights from Louisville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 11/4

3:20 pm-9:05 pm

1 stop6h 45m

Chicago Midway

jue. 11/6

7:15 pm-9:30 pm

Nonstop1h 15m

$107

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 11/4

11:45 am-8:30 pm

2 stops9h 45m

Chicago Midway

jue. 11/6

7:15 pm-9:30 pm

Nonstop1h 15m

$112

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mar. 10/14

6:45 am-7:18 am

Nonstop1h 33m

Chicago O'Hare Intl

vie. 10/17

8:21 pm-10:56 pm

Nonstop1h 35m

$134

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mar. 11/4

9:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

jue. 11/6

7:30 am-9:59 am

Nonstop1h 29m

$152

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mar. 10/7

7:00 am-7:38 am

Nonstop1h 38m

Chicago O'Hare Intl

mar. 10/14

4:00 pm-6:33 pm

Nonstop1h 33m

$157

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mar. 10/14

6:45 am-7:18 am

Nonstop1h 33m

Chicago O'Hare Intl

mar. 10/21

8:28 pm-11:03 pm

Nonstop1h 35m

$164

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

mié. 11/12

6:00 am-10:19 am

1 stop5h 19m

Chicago O'Hare Intl

sáb. 11/15

6:22 pm-11:57 pm

1 stop4h 35m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 11/11

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

mar. 11/11

5:34 pm-12:06 am

1 stop5h 32m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mié. 11/12

6:00 am-9:12 am

1 stop28h 12m

Chicago Midway

lun. 11/17

9:27 am-11:45 pm

1 stop13h 18m

$203

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

jue. 10/30

7:15 am-12:26 pm

1 stop30h 11m

Chicago O'Hare Intl

jue. 11/6

5:59 pm-9:04 am

1 stop14h 05m

$208

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 Louisville 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 cheapest month to fly to Chicago?

The month of April is, on average, the cheapest month to fly to Chicago from Louisville, with most prices found around $207. If you’re not able to fly to Chicago in April, then August is your next best option. Flight prices from Louisville to Chicago during August average around $239.

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 Thursday when prices can be found for as low as $495. 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 Louisville to Chicago for around $721.

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 Louisville to Chicago during this time can be as low as $528. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $850.

What is the cheapest Louisville Intl to Chicago flight route?

Fly from Louisville Intl to Chicago Midway for the best Louisville Intl - 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 Louisville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $288 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Louisville for as low as $196 on momondo.

What cabin class options are available on Louisville Intl to Chicago flights?

There are 4 cabin classes available to choose from on Louisville Intl 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 Louisville to Chicago flights?

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

How have Louisville to Chicago flight prices changed over time?

As of September 2025, prices for Louisville to Chicago flights are approximately 46% cheaper when compared to flights at the same time last year.

When to book flights from Louisville to Chicago

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

Cheap Louisville to Chicago (SDF to CHI) flight deals and tips

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

Best Price Found

$178

Fastest flight time

1h 15m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Louisville in the past 72 hours is $178. The best round-trip flight deal from Louisville to Chicago found on momondo in the last 72 hours is $238.
The fastest flight from Louisville to Chicago takes 1h 15m
Direct flights go from Louisville to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Louisville Intl to Chicago by plane?

    Chicago is 269.2 mi away from Louisville Intl. Typically, this will take 1h 15m by plane in normal conditions.

  • When did momondo last update prices for flights from Louisville Intl Airport to Chicago?

    Prices for flights from Louisville Intl Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Louisville Intl Airport to Chicago?

  • How old do you have to be to fly from Louisville Intl Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Louisville Intl 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 Louisville to Chicago?

  • What is the most popular airline from Louisville to Chicago?

Best airlines flying from Louisville to Chicago

Compare and see reviews for airlines that fly from Louisville to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $97Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $123Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights

  • Southwest Flights From Louisville to Chicago

    Across 14 Southwest flights from Louisville to Chicago this week, the average price was $260, with the best Southwest deals starting from $97 round-trip. 4,242 users have rated Southwest on momondo, with an average score of 8.0/10.

  • United Airlines Flights From Louisville to Chicago

    $123 is the best United Airlines flight deal from Louisville to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $298, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,929 user reviews) flies into Chicago from Louisville 41 times in an average week so prices can vary.

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
Lansing
Portage
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 Louisville to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Louisville to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

momondo does allow users to show only those flights to Chicago from Louisville which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Louisville to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Louisville to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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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