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Midway

$97+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
LIT — MDW
May 24 — May 311
Sun 5/24
Sun 5/31
1 adult, Economy
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Cheap 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 April 24, 2026.

This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:05 pm
LIT
-
MDW
2 stops6h 30m
Southwest
Wed 6/105:05 am
MDW
-
LIT
1 stop6h 05m
Southwest
Deal found 4/21$208
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/53:45 pm
LIT
-
MDW
1 stop8h 25m
Southwest
Tue 6/93:10 pm
MDW
-
LIT
1 stop7h 40m
Southwest
Deal found 4/22$235
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/113:40 pm
LIT
-
MDW
1 stop7h 50m
Southwest
Wed 5/135:30 am
MDW
-
LIT
1 stop6h 40m
Southwest
Deal found 4/20$247
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/123:25 pm
LIT
-
MDW
1 stop6h 50m
Southwest
Thu 5/145:30 am
MDW
-
LIT
1 stop3h 30m
Southwest
Deal found 4/20$250
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:50 pm
LIT
-
MDW
2 stops6h 05m
Southwest
Wed 6/35:30 am
MDW
-
LIT
1 stop6h 40m
Southwest
Deal found 4/23$255
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:50 pm
LIT
-
MDW
2 stops6h 05m
Southwest
Mon 5/186:15 pm
MDW
-
LIT
1 stop5h 20m
Southwest
Deal found 4/22$264
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:25 pm
LIT
-
MDW
1 stop6h 50m
Southwest
Wed 5/274:50 pm
MDW
-
LIT
1 stop5h 45m
Southwest
Deal found 4/22$265
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:45 pm
LIT
-
MDW
1 stop5h 20m
Southwest
Tue 6/93:55 pm
MDW
-
LIT
2 stops6h 55m
Southwest
Deal found 4/20$269

Find flight deals from Little Rock to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Little Rock (LIT) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Southwest)

One-way from

$97
(Southwest)

Popular in

March

Cheapest in

February

Average price

$450
Provider with most accurate pricing for Little Rock-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Little Rock-Chicago Midway flights.
Search Deals
From Little Rock to Chicago Midway
Search Deals
One-way flight from Little Rock to Chicago Midway
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Little Rock to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2026.
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

Cheapest round-trip

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 5/8

5:50 pm-11:55 pm

1 stop6h 05m

Chicago Midway

Tue 5/19

4:40 pm-10:35 pm

2 stops5h 55m

$290
Quickest round-trip

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 7/15

6:00 pm-10:00 pm

1 stop4h 00m

Chicago Midway

Fri 7/17

5:00 am-10:45 am

1 stop5h 45m

$304

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Mon 5/18

5:50 pm-11:55 pm

1 stop6h 05m

Chicago Midway

Wed 5/20

5:30 am-12:10 pm

1 stop6h 40m

$304

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 5/27

5:40 pm-9:45 pm

1 stop4h 05m

Chicago Midway

Sun 5/31

5:00 am-11:30 am

1 stop6h 30m

$306

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Thu 5/7

5:50 pm-11:55 pm

1 stop6h 05m

Chicago Midway

Sat 5/16

9:10 am-1:20 pm

1 stop4h 10m

$308

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 6/5

7:05 pm-1:00 am

1 stop5h 55m

Chicago Midway

Sun 6/7

5:00 am-10:15 am

1 stop5h 15m

$316

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 6/12

7:05 pm-1:00 am

1 stop5h 55m

Chicago Midway

Fri 6/19

4:20 pm-11:05 pm

1 stop6h 45m

$328

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Thu 5/28

5:50 pm-11:55 pm

2 stops6h 05m

Chicago Midway

Sun 5/31

5:00 am-11:30 am

1 stop6h 30m

$333

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 5/27

5:25 am-11:56 am

1 stop6h 31m

Chicago Midway

Sun 5/31

6:23 am-11:13 am

1 stop4h 50m

$335

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Thu 5/7

12:05 pm-8:30 pm

2 stops8h 25m

Chicago Midway

Mon 5/11

6:00 am-3:05 pm

1 stop9h 05m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Little Rock to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Little Rock to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Little Rock-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Little Rock-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Little Rock-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Little Rock-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Little Rock-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, February is the cheapest month in which you can book a flight from Little Rock to Chicago Midway Airport (average of $259). Flying from Little Rock to Chicago Midway Airport in March is currently the most expensive (average of $889). 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.

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

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated April 24, 2026.
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
4,334 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,334 reviews
Southwest
8.0
Very good
4,334 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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?

    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 $290, Southwest can have you in Chicago Midway Airport from Little Rock in 6h 05m. There are 544 mi between Little Rock and Chicago Midway Airport.

  • 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 $259. Southwest is 34% 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, February is the cheapest month in which you can book a flight from Little Rock to Chicago Midway Airport (average of $259). Flying from Little Rock to Chicago Midway Airport in March is currently the most expensive (average of $889). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Little Rock to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Little Rock to Midway

Discover the top airline that operate flights from Little Rock to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$259Average$383FlexibilityNo cancel feeOn-time63%

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