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Cheap flights from Little Rock to Chicago from $145

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Little Rock to Chicago departing on 5/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Find the cheapest flights from Little Rock to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:25 am - 10:00 am
LIT
-
MDW
4h 35m
1 stop
Delta Logo
5:10 pm - 11:39 pm
MDW
-
LIT
6h 29m
1 stop
$289Delta
Tue, May 26 - Sat, May 30
Southwest Logo
1:05 pm - 8:10 pm
LIT
-
MDW
7h 05m
2 stops
Southwest Logo
4:00 pm - 9:55 pm
MDW
-
LIT
5h 55m
1 stop
$294Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
1:05 pm - 8:10 pm
LIT
-
MDW
7h 05m
2 stops
Southwest Logo
4:40 pm - 10:35 pm
MDW
-
LIT
5h 55m
2 stops
$299Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
4:25 pm - 9:05 pm
LIT
-
MDW
4h 40m
1 stop
Southwest Logo
5:30 am - 12:10 pm
MDW
-
LIT
6h 40m
1 stop
$304Southwest
Sat, May 23 - Tue, May 26
Delta Logo
5:25 am - 10:00 am
LIT
-
MDW
4h 35m
1 stop
Delta Logo
6:23 am - 11:13 am
MDW
-
LIT
4h 50m
1 stop
$309Delta
Tue, May 12 - Mon, Jun 1
Southwest Logo
1:05 pm - 8:10 pm
LIT
-
MDW
7h 05m
2 stops
Southwest Logo
6:15 pm - 11:35 pm
MDW
-
LIT
5h 20m
1 stop
$314Southwest
Wed, May 13 - Mon, Jun 1
Southwest Logo
1:05 pm - 8:10 pm
LIT
-
MDW
7h 05m
2 stops
Southwest Logo
3:10 pm - 10:50 pm
MDW
-
LIT
7h 40m
1 stop
$315Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
7:05 pm - 1:00 am
LIT
-
MDW
5h 55m
1 stop
Southwest Logo
6:30 am - 11:10 am
MDW
-
LIT
4h 40m
1 stop
$319Southwest
Thu, Jul 2 - Wed, Jul 8
Southwest Logo
2:40 pm - 9:55 pm
LIT
-
MDW
7h 15m
2 stops
Southwest Logo
6:00 am - 11:10 am
MDW
-
LIT
5h 10m
1 stop
$324Southwest
Thu, Sep 24 - Tue, Sep 29
Southwest Logo
6:00 pm - 12:05 am
LIT
-
MDW
6h 05m
1 stop
Southwest Logo
7:20 am - 3:05 pm
MDW
-
LIT
7h 45m
1 stop
$328Southwest
Tue, Jun 23 - Sat, Jun 27

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Southwest flights from Little Rock to Chicago Midway Airport

Our best Southwest deals on Little Rock to Chicago Midway Airport flight tickets
Southwest
May 26
LIT1:05 pmLittle Rock
7h 05m
2 stops
MDW8:10 pmChicago Midway
Jun 2
MDW4:00 pmChicago Midway
5h 55m
1 stop
LIT9:55 pmLittle Rock
$294
Southwest
May 26
LIT1:05 pmLittle Rock
7h 05m
2 stops
MDW8:10 pmChicago Midway
Jun 2
MDW4:40 pmChicago Midway
5h 55m
2 stops
LIT10:35 pmLittle Rock
$299
Southwest
May 23
LIT4:25 pmLittle Rock
4h 40m
1 stop
MDW9:05 pmChicago Midway
May 26
MDW5:30 amChicago Midway
6h 40m
1 stop
LIT12:10 pmLittle Rock
$304

Delta flights from Little Rock to Chicago Midway Airport

Our best Delta deals on Little Rock to Chicago Midway Airport flight tickets
Delta
May 26
LIT5:25 amLittle Rock
4h 35m
1 stop
MDW10:00 amChicago Midway
May 30
MDW5:10 pmChicago Midway
6h 29m
1 stop
LIT11:39 pmLittle Rock
$289
Delta
May 12
LIT5:25 amLittle Rock
4h 35m
1 stop
MDW10:00 amChicago Midway
Jun 1
MDW6:23 amChicago Midway
4h 50m
1 stop
LIT11:13 amLittle Rock
$309
Delta
Jun 6
LIT3:13 pmLittle Rock
5h 56m
1 stop
MDW9:09 pmChicago Midway
Jun 9
MDW6:00 amChicago Midway
5h 07m
1 stop
LIT11:07 amLittle Rock
$334

momondo Fare Finder

 
Customize your flight search to find flights from Little Rock to Chicago Midway Airport 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 May 2, 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

Tue 5/26

5:25 am-10:00 am

1 stop4h 35m

Chicago Midway

Sat 5/30

5:10 pm-11:39 pm

1 stop6h 29m

$289

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 5/26

1:05 pm-8:10 pm

2 stops7h 05m

Chicago Midway

Tue 6/2

4:00 pm-9:55 pm

1 stop5h 55m

$294

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 5/26

1:05 pm-8:10 pm

2 stops7h 05m

Chicago Midway

Tue 6/2

4:40 pm-10:35 pm

2 stops5h 55m

$299

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Sat 5/23

4:25 pm-9:05 pm

1 stop4h 40m

Chicago Midway

Tue 5/26

5:30 am-12:10 pm

1 stop6h 40m

$304
Quickest round-trip

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 5/12

5:25 am-10:00 am

1 stop4h 35m

Chicago Midway

Mon 6/1

6:23 am-11:13 am

1 stop4h 50m

$309

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 5/13

1:05 pm-8:10 pm

2 stops7h 05m

Chicago Midway

Mon 6/1

6:15 pm-11:35 pm

1 stop5h 20m

$314

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 6/2

1:05 pm-8:10 pm

2 stops7h 05m

Chicago Midway

Tue 6/9

3:10 pm-10:50 pm

1 stop7h 40m

$315

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Thu 7/2

7:05 pm-1:00 am

1 stop5h 55m

Chicago Midway

Wed 7/8

6:30 am-11:10 am

1 stop4h 40m

$319

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Thu 9/24

2:40 pm-9:55 pm

2 stops7h 15m

Chicago Midway

Tue 9/29

6:00 am-11:10 am

1 stop5h 10m

$324

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 6/23

6:00 pm-12:05 am

1 stop6h 05m

Chicago Midway

Sat 6/27

7:20 am-3:05 pm

1 stop7h 45m

$328

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Little Rock to Chicago Midway Airport

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 Little Rock and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Little Rock, with most prices found around $259. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Little Rock during the month August is also very affordable. Most momondo users find prices during this month for around $298.

When to book flights from Little Rock to Chicago Midway Airport

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

Cheap Little Rock to Chicago Midway Airport (LIT to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Little Rock to Chicago Midway Airport

Fastest flight time

4h 00m

Direct flights

None
The fastest flight from Little Rock to Chicago Midway Airport takes 4h 00m
There are no direct flights from Little Rock to Chicago Midway Airport. There are no popular flight routes from Little Rock to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Little Rock to Chicago Midway Airport

  • How far is Little Rock to Chicago Midway by plane?

    Little Rock and Chicago Midway are 544.7 mi apart from one another. In terms of flight time, this usually takes a little over 4h 00m.

  • When did momondo last update prices for flights from Little Rock Airport to Chicago Midway Airport?

    Prices for flights from Little Rock Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Little Rock Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Little Rock Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Little Rock Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Little Rock to Chicago Midway Airport?

Best airlines flying from Little Rock to Chicago Midway Airport

Compare and see reviews for airlines that fly from Little Rock to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $259Free CancellationRating
8.0
4,314 reviews
Search Southwest flights

Traveling to a place near Chicago?

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Why use momondo?

Why should I use momondo to find a flight deal from Little Rock to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Little Rock to Chicago for you.

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

Yes. All flights to Chicago from Little Rock on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Little Rock to Chicago?

Once all potential Little Rock 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 Little Rock to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Little Rock to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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