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Cheap flights from Little Rock to Chicago from $115

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 10/17. 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 Little Rock to Chicago

Cheap round-trip flights

Southwest Logo
6:10 am - 11:25 amLIT-MDW
5h 15m1 stop
Southwest Logo
5:00 am - 9:50 amMDW-LIT
4h 50m1 stop
$140Southwest
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Tue, Nov 4 - Wed, Nov 5
Southwest Logo
8:10 am - 2:55 pmLIT-MDW
6h 45m2 stops
Southwest Logo
5:00 am - 9:50 amMDW-LIT
4h 50m1 stop
$145Southwest
Find Deal
Tue, Nov 4 - Wed, Nov 5
Southwest Logo
4:05 pm - 10:35 pmLIT-MDW
6h 30m2 stops
Southwest Logo
11:25 am - 8:15 pmMDW-LIT
8h 50m2 stops
$150Southwest
Find Deal
Tue, Nov 4 - Wed, Nov 5
Southwest Logo
4:40 pm - 11:15 pmLIT-MDW
6h 35m2 stops
Southwest Logo
5:45 am - 11:25 amMDW-LIT
5h 40m1 stop
$163Southwest
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Mon, Oct 13 - Wed, Oct 15
Frontier Logo
8:21 pm - 1:38 pmLIT-MDW
17h 17m2 stops
Frontier Logo
9:26 pm - 7:26 pmMDW-LIT
22h 00m2 stops
$227Frontier
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Mon, Oct 20 - Thu, Oct 23
Delta Logo
5:15 am - 9:48 amLIT-MDW
4h 33m1 stop
Delta Logo
6:00 am - 10:28 amMDW-LIT
4h 28m1 stop
$249Delta
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Sat, Sep 27 - Tue, Sep 30
Delta Logo
4:32 pm - 9:36 pmLIT-MDW
5h 04m1 stop
Delta Logo
6:00 am - 10:28 amMDW-LIT
4h 28m1 stop
$258Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
Delta Logo
4:32 pm - 9:36 pmLIT-MDW
5h 04m1 stop
Delta Logo
6:00 am - 10:28 amMDW-LIT
4h 28m1 stop
$268Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
Frontier Logo
8:21 pm - 1:38 pmLIT-MDW
17h 17m2 stops
Frontier Logo
6:24 pm - 7:26 pmMDW-LIT
25h 02m1 stop
$278Frontier
Find Deal
Mon, Oct 20 - Thu, Oct 23
Frontier Logo
8:21 pm - 10:21 amLIT-MDW
14h 00m2 stops
Frontier Logo
6:24 pm - 7:35 pmMDW-LIT
25h 11m1 stop
$368Frontier
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Fri, Oct 17 - Sun, Oct 19

Southwest flights from Little Rock to Chicago Midway Airport

Our best Southwest deals on Little Rock to Chicago Midway Airport flight tickets
Southwest
Nov 4
LIT6:10 amLittle Rock
5h 15m
1 stop
MDW11:25 amChicago Midway
Nov 5
MDW5:00 amChicago Midway
4h 50m
1 stop
LIT9:50 amLittle Rock
$140
Find similar
Southwest
Nov 4
LIT8:10 amLittle Rock
6h 45m
2 stops
MDW2:55 pmChicago Midway
Nov 5
MDW5:00 amChicago Midway
4h 50m
1 stop
LIT9:50 amLittle Rock
$145
Find similar
Southwest
Nov 4
LIT4:05 pmLittle Rock
6h 30m
2 stops
MDW10:35 pmChicago Midway
Nov 5
MDW11:25 amChicago Midway
8h 50m
2 stops
LIT8:15 pmLittle Rock
$150
Find similar

Delta flights from Little Rock to Chicago Midway Airport

Our best Delta deals on Little Rock to Chicago Midway Airport flight tickets
Delta
Sep 27
LIT5:15 amLittle Rock
4h 33m
1 stop
MDW9:48 amChicago Midway
Sep 30
MDW6:00 amChicago Midway
4h 28m
1 stop
LIT10:28 amLittle Rock
$249
Find similar
Delta
Oct 3
LIT4:32 pmLittle Rock
5h 04m
1 stop
MDW9:36 pmChicago Midway
Oct 5
MDW6:00 amChicago Midway
4h 28m
1 stop
LIT10:28 amLittle Rock
$258
Find similar
Delta
Oct 3
LIT4:32 pmLittle Rock
5h 04m
1 stop
MDW9:36 pmChicago Midway
Oct 5
MDW6:00 amChicago Midway
4h 28m
1 stop
LIT10:28 amLittle Rock
$268
Find similar

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 September 15, 2025.
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

Tue 11/4

6:10 am-11:25 am

1 stop5h 15m

Chicago Midway

Wed 11/5

5:00 am-9:50 am

1 stop4h 50m

$140

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 11/4

8:10 am-2:55 pm

2 stops6h 45m

Chicago Midway

Wed 11/5

5:00 am-9:50 am

1 stop4h 50m

$145

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Tue 11/4

4:05 pm-10:35 pm

2 stops6h 30m

Chicago Midway

Wed 11/5

11:25 am-8:15 pm

2 stops8h 50m

$150

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Mon 10/13

4:40 pm-11:15 pm

2 stops6h 35m

Chicago Midway

Wed 10/15

5:45 am-11:25 am

1 stop5h 40m

$163

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Mon 10/20

8:21 pm-1:38 pm

2 stops17h 17m

Chicago Midway

Thu 10/23

9:26 pm-7:26 pm

2 stops22h 00m

$227

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Sat 9/27

5:15 am-9:48 am

1 stop4h 33m

Chicago Midway

Tue 9/30

6:00 am-10:28 am

1 stop4h 28m

$249

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 10/3

4:32 pm-9:36 pm

1 stop5h 04m

Chicago Midway

Sun 10/5

6:00 am-10:28 am

1 stop4h 28m

$258

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 10/3

4:32 pm-9:36 pm

1 stop5h 04m

Chicago Midway

Sun 10/5

6:00 am-10:28 am

1 stop4h 28m

$268

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Mon 10/20

8:21 pm-1:38 pm

2 stops17h 17m

Chicago Midway

Thu 10/23

6:24 pm-7:26 pm

1 stop25h 02m

$278

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 10/17

8:21 pm-10:21 am

2 stops14h 00m

Chicago Midway

Sun 10/19

6:24 pm-7:35 pm

1 stop25h 11m

$368

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Little Rock, with most prices found around $253. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Little Rock during the month March is also very affordable. Most momondo users find prices during this month for around $268.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Little Rock. The lowest ticket price found for a Tuesday departure recently was $288. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from Little Rock because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $498.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Little Rock in the morning is the least expensive time of day to depart. momondo users have found prices as low as $340 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $373. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Direct flights

None
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.
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  • 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 3h 10m.

  • 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 $268Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Porter
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Saint John

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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