How long is the flight from Little Rock to Chicago Midway Airport?

For as low as $229, Southwest can have you in Chicago Midway Airport from Little Rock in 4h 27m. There are 544 mi between Little Rock and Chicago Midway Airport. This flight may include one or multiple stops.

What is the cheapest airline to fly from Little Rock to Chicago Midway Airport round-trip?

Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $268. Southwest is 21% cheaper than the average price of flights available within the next 90 days to this destination.

What is the cheapest day to fly from Little Rock to Chicago Midway Airport?

Travelers seeking maximum savings on their Little Rock to Chicago Midway Airport flight should consider departing on Thursday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest day to fly round-trip from Little Rock to Chicago Midway Airport?

Thursday flights are generally found to be more expensive for flights from Little Rock to Chicago Midway Airport. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago Midway Airport.

How far in advance should I book a flight from Little Rock to Chicago Midway Airport?

Travelers have found it’s best to book a flight 44 days in advance to save up to 21% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 44 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Little Rock to Chicago Midway Airport 1-2 weeks in advance for as low as $254, or $305 for flights within the next 24 hours.

What is the cheapest month to fly from Little Rock to Chicago Midway Airport?

November can be a great time to fly to Chicago Midway Airport from Little Rock with a flight ticket averaging about $304. Cheapflights users have found deals in the month of November for as cheap as $199. The most expensive prices can be found in the month of June.

What airport do you fly from for flights from Little Rock to Chicago Midway?

Located just 4.0 mi from the city center, Little Rock is the airport most travelers will use when flying to Chicago Midway from Little Rock. Booking flights from Little Rock (LIT) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 1 airline.

Can I find deals for flights from Little Rock to Midway that include hotel bookings?

Yes. In addition to deals on Little Rock to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Little Rock to Midway?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Little Rock to Midway.

Can I find deals for business class flights from Little Rock to Midway?

Yes. Cheapflights offers flight deals from Little Rock to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$70+ Cheap Flights from Little Rock to Chicago Midway Airport

Q: How much does it cost to fly round-trip from Little Rock to Chicago Midway Airport?

Airfare is below average for this route at the moment. Little Rock to Chicago Midway Airport flights typically cost between $316 and $367 in October. The cheapest round-trip price found within the last 3 days was $148 on Southwest (Oct 8-Oct 15).

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Cheap flight deals from Little Rock to Midway

Round-trip from	$148 (Southwest)
One-way from	$70 (Southwest)
Popular in	December
Cheapest in	January
Average price	$353

From Little Rock to Chicago Midway

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One-way flight from Little Rock to Chicago Midway

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Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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Find flight deals from Little Rock to Midway

Cheapest flights from Little Rock to Midway
Explore the most affordable flight options available from Little Rock to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Wed 10/86:30 pmLIT - MDW

1 stop5h 35mSouthwest

Wed 10/155:45 amMDW - LIT

1 stop5h 40mSouthwest

Deal found 9/10

$148

Sat 9/275:50 amLIT - MDW

1 stop6h 45mSouthwest

Tue 9/305:40 pmMDW - LIT

1 stop4h 20mSouthwest

Deal found 9/11

$212

Thu 10/26:00 pmLIT - MDW

1 stop6h 05mSouthwest

Mon 10/63:30 pmMDW - LIT

1 stop7h 25mSouthwest

Deal found 9/9

$216

Tue 11/255:25 amLIT - MDW

1 stop4h 27mDelta

Fri 11/285:34 pmMDW - LIT

1 stop5h 59mDelta

Deal found 9/10

$229

Thu 9/257:05 pmLIT - MDW

1 stop4h 45mSouthwest

Sun 9/286:00 amMDW - LIT

1 stop9h 25mSouthwest

Deal found 9/11

$254

Sun 9/284:00 pmLIT - MDW

1 stop5h 30mSouthwest

Wed 10/16:25 amMDW - LIT

1 stop5h 15mSouthwest

Deal found 9/11

$267

Wed 9/2412:25 pmLIT - MDW

1 stop4h 45mSouthwest

Sat 9/2712:25 pmMDW - LIT

1 stop8h 05mSouthwest

Deal found 9/11

$274

Best flights from Little Rock to Midway
Discover carefully curated flight deals from Little Rock to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2025.

Wed 10/86:30 pmLIT - MDW

1 stop5h 35mSouthwest

Wed 10/155:45 amMDW - LIT

1 stop5h 40mSouthwest

Deal found 9/10

$148

Tue 11/255:25 amLIT - MDW

1 stop4h 27mDelta

Fri 11/285:34 pmMDW - LIT

1 stop5h 59mDelta

Deal found 9/10

$229

Thu 10/26:00 pmLIT - MDW

1 stop6h 05mSouthwest

Mon 10/63:30 pmMDW - LIT

1 stop7h 25mSouthwest

Deal found 9/9

$216

Mon 9/227:05 pmLIT - MDW

1 stop4h 45mSouthwest

Thu 9/252:35 pmMDW - LIT

1 stop8h 40mSouthwest

Deal found 9/10

$284

Fri 9/267:05 pmLIT - MDW

1 stop4h 45mSouthwest

Mon 9/296:05 pmMDW - LIT

1 stop5h 10mSouthwest

Deal found 9/9

$299

Tue 11/257:40 pmLIT - MDW

1 stop5h 05mSouthwest

Fri 11/282:55 pmMDW - LIT

2 stops8h 40mSouthwest

Deal found 9/8

$303

Fri 10/36:00 pmLIT - MDW

1 stop6h 05mSouthwest

Sun 10/57:45 amMDW - LIT

1 stop5h 20mSouthwest

Deal found 9/10

$304

Fri 9/195:20 pmLIT - MDW

1 stop3h 05mSouthwest

Sat 9/206:35 amMDW - LIT

1 stop8h 20mSouthwest

Deal found 9/8

$309

Last-minute flights from Little Rock to Midway
Discover last-minute flight deals from Little Rock to Midway. Data last updated September 11, 2025 and is based on user searches.

Mon 9/227:05 pmLIT - MDW

1 stop4h 45mSouthwest

Thu 9/252:35 pmMDW - LIT

1 stop8h 40mSouthwest

Deal found 9/11

$284

Wed 9/2412:25 pmLIT - MDW

1 stop4h 45mSouthwest

Sat 9/2712:25 pmMDW - LIT

1 stop8h 05mSouthwest

Deal found 9/11

$274

Thu 9/257:05 pmLIT - MDW

1 stop4h 45mSouthwest

Sun 9/286:00 amMDW - LIT

1 stop9h 25mSouthwest

Deal found 9/11

$254

Sat 9/275:50 amLIT - MDW

1 stop6h 45mSouthwest

Tue 9/305:40 pmMDW - LIT

1 stop4h 20mSouthwest

Deal found 9/11

$212

Sun 9/284:00 pmLIT - MDW

1 stop5h 30mSouthwest

Wed 10/16:25 amMDW - LIT

1 stop5h 15mSouthwest

Deal found 9/11

$267

Thu 10/26:00 pmLIT - MDW

1 stop6h 05mSouthwest

Mon 10/63:30 pmMDW - LIT

1 stop7h 25mSouthwest

Deal found 9/9

$216

Wed 10/86:30 pmLIT - MDW

1 stop5h 35mSouthwest

Wed 10/155:45 amMDW - LIT

1 stop5h 40mSouthwest

Deal found 9/10

$148

One-way flights from Little Rock to Midway
Search for one-way flight options from Little Rock to Midway. Find affordable one-way fares based on user searches. Data last updated September 11, 2025.

Wed 10/86:30 pmLIT - MDW

1 stop5h 35mSouthwest

Deal found 9/10

$70

Wed 10/296:30 pmLIT - MDW

1 stop5h 35mSouthwest

Deal found 9/11

$78

Sat 12/136:25 amLIT - MDW

1 stop8h 55mSouthwest

Deal found 9/11

$94

Sun 11/95:50 amLIT - MDW

1 stop4h 05mSouthwest

Deal found 9/10

$106

Mon 11/34:05 pmLIT - MDW

1 stop4h 25mSouthwest

Deal found 9/11

$108

Thu 11/65:50 amLIT - MDW

1 stop4h 05mSouthwest

Deal found 9/11

$115

Fri 11/71:35 pmLIT - MDW

1 stop9h 05mSouthwest

Deal found 9/11

$120

Fri 10/36:00 pmLIT - MDW

1 stop6h 05mSouthwest

Deal found 9/11

$125

Thu 11/66:55 pmLIT - MDW

2 stops41h 42mFrontier

Deal found 9/11

$131

Cheapflights Fare Finder

Use the filters below to find and compare flights from Little Rock to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 10/8

6:30 pm-12:05 am

1 stop5h 35m

Chicago Midway

Wed 10/15

5:45 am-11:25 am

1 stop5h 40m

$148

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Thu 10/2

6:00 pm-12:05 am

1 stop6h 05m

Chicago Midway

Mon 10/6

3:30 pm-10:55 pm

1 stop7h 25m

$216

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 11/25

5:25 am-9:52 am

1 stop4h 27m

Chicago Midway

Fri 11/28

5:34 pm-11:33 pm

1 stop5h 59m

$229

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Mon 9/22

7:05 pm-11:50 pm

1 stop4h 45m

Chicago Midway

Thu 9/25

2:35 pm-11:15 pm

1 stop8h 40m

$284

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 9/26

7:05 pm-11:50 pm

1 stop4h 45m

Chicago Midway

Mon 9/29

6:05 pm-11:15 pm

1 stop5h 10m

$299

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 11/25

7:40 pm-12:45 am

1 stop5h 05m

Chicago Midway

Fri 11/28

2:55 pm-11:35 pm

2 stops8h 40m

$303

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 10/3

6:00 pm-12:05 am

1 stop6h 05m

Chicago Midway

Sun 10/5

7:45 am-1:05 pm

1 stop5h 20m

$304

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 9/19

5:20 pm-8:25 pm

1 stop3h 05m

Chicago Midway

Sat 9/20

6:35 am-2:55 pm

1 stop8h 20m

$309

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 10/29

6:30 pm-12:05 am

1 stop5h 35m

$78

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 10/8

6:30 am-2:05 pm

2 stops7h 35m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 19 results

Best time to book a flight from Little Rock to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Little Rock with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Little Rock to Chicago Midway Airport

What is the cheapest month to book a flight from Little Rock to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Little Rock to Chicago Midway Airport (average of $160). Flying from Little Rock to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from LIT to MDW?

When flying from Little Rock to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 9% versus a flight at noon.

How much does it cost to fly round-trip from Little Rock to Chicago Midway Airport?

Reviews of airlines servicing Midway

Read through reviews of airlines operating flights from Little Rock to Chicago Midway Airport, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,248 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Southwest

8.0

Very good

4,248 reviews

Southwest

8.0

Very good

4,248 reviews

Reviews

1 / 20

2.0

Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

What airport do you fly from for flights from Little Rock to Chicago Midway?
Located just 4.0 mi from the city center, Little Rock is the airport most travelers will use when flying to Chicago Midway from Little Rock. Booking flights from Little Rock (LIT) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 1 airline.
How long is the flight from Little Rock to Chicago Midway Airport?
For as low as $229, Southwest can have you in Chicago Midway Airport from Little Rock in 4h 27m. There are 544 mi between Little Rock and Chicago Midway Airport. This flight may include one or multiple stops.
What is the cheapest airline to fly from Little Rock to Chicago Midway Airport round-trip?
Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $268. Southwest is 21% cheaper than the average price of flights available within the next 90 days to this destination.
Can I find deals for flights from Little Rock to Midway that include hotel bookings?
Yes. In addition to deals on Little Rock to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Little Rock to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Little Rock to Midway.
Can I find deals for business class flights from Little Rock to Midway?
Yes. Cheapflights offers flight deals from Little Rock to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Little Rock to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Little Rock to Chicago Midway Airport (average of $160). Flying from Little Rock to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Hammond

Benton Harbor

Porter

Chesterton

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Top airline flying from Little Rock to Midway

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$268	Average$334	FlexibilityNo cancel fee	On-time63%

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$70+ Cheap flights from Little Rock (LIT) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/8. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Little Rock to Midway with Cheapflights

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2. Select your favorite providers

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Cheap flight deals from Little Rock to Midway

Round-trip from

One-way from

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Cheapest in

Average price

Find flight deals from Little Rock to Midway

Cheapest flights from Little Rock to MidwayExplore the most affordable flight options available from Little Rock to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Explore the most affordable flight options available from Little Rock to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Little Rock to Chicago Midway Airport that are best for you.

Best time to book a flight from Little Rock to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Little Rock with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Little Rock to Chicago Midway Airport

What is the cheapest month to book a flight from Little Rock to Chicago Midway Airport?

What is the cheapest time of day to fly from LIT to MDW?

How much does it cost to fly round-trip from Little Rock to Chicago Midway Airport?

Reviews of airlines servicing Midway

Read through reviews of airlines operating flights from Little Rock to Chicago Midway Airport, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Little Rock to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Little Rock to Chicago Midway?

How long is the flight from Little Rock to Chicago Midway Airport?

What is the cheapest airline to fly from Little Rock to Chicago Midway Airport round-trip?

Can I find deals for flights from Little Rock to Midway that include hotel bookings?

How can I find direct flights from Little Rock to Midway?

Can I find deals for business class flights from Little Rock to Midway?

What is the cheapest month to book a flight from Little Rock to Chicago Midway Airport?

Traveling to a place near Chicago Midway Airport?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Little Rock to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Little Rock to Midway

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Cheapest flights from Little Rock to Midway
Explore the most affordable flight options available from Little Rock to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.