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Cheap flights from Little Rock to Chicago from $126

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 2/9. 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

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Find the cheapest flights from Little Rock to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:36 am - 4:29 pm
LIT
-
MDW
6h 53m1 stop
Delta Logo
6:25 am - 10:54 am
MDW
-
LIT
4h 29m1 stop
$229Delta
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
6:15 am - 9:30 am
LIT
-
MDW
3h 15m1 stop
Southwest Logo
1:15 pm - 9:10 pm
MDW
-
LIT
7h 55m2 stops
$264Southwest
Wed, Jan 21 - Wed, Jan 28
Delta Logo
12:12 pm - 4:36 pm
LIT
-
MDW
4h 24m1 stop
Delta Logo
5:31 pm - 11:39 pm
MDW
-
LIT
6h 08m1 stop
$268Delta
Sat, Apr 25 - Fri, May 1
Southwest Logo
12:40 pm - 8:30 pm
LIT
-
MDW
7h 50m1 stop
Southwest Logo
5:20 am - 10:05 am
MDW
-
LIT
4h 45m1 stop
$283Southwest
Sat, Jan 31 - Sun, Feb 1
Southwest Logo
9:05 am - 4:45 pm
LIT
-
MDW
7h 40m2 stops
Southwest Logo
1:15 pm - 9:10 pm
MDW
-
LIT
7h 55m2 stops
$285Southwest
Wed, Jan 21 - Wed, Jan 28
Southwest Logo
5:40 am - 4:25 pm
LIT
-
MDW
10h 45m2 stops
Southwest Logo
5:20 am - 10:05 am
MDW
-
LIT
4h 45m1 stop
$294Southwest
Sat, Jan 31 - Sun, Feb 1
Southwest Logo
6:35 am - 11:35 am
LIT
-
MDW
5h 00m1 stop
Southwest Logo
6:00 am - 2:50 pm
MDW
-
LIT
8h 50m2 stops
$296Southwest
Sat, Jan 17 - Sat, Jan 24
Delta Logo
3:58 pm - 10:07 pm
LIT
-
MDW
6h 09m1 stop
Delta Logo
5:31 pm - 11:38 pm
MDW
-
LIT
6h 07m1 stop
$304Delta
Fri, Jan 9 - Sun, Jan 11
Delta Logo
5:25 am - 9:54 am
LIT
-
MDW
4h 29m1 stop
Delta Logo
6:40 pm - 11:36 pm
MDW
-
LIT
4h 56m1 stop
$307Delta
Sun, Mar 1 - Wed, Mar 4
Southwest Logo
5:40 am - 4:25 pm
LIT
-
MDW
10h 45m2 stops
Southwest Logo
8:15 am - 4:05 pm
MDW
-
LIT
7h 50m2 stops
$334Southwest
Sat, Jan 31 - Sun, Feb 1

Delta flights from Little Rock to Chicago Midway Airport

Our best Delta deals on Little Rock to Chicago Midway Airport flight tickets
Delta
Jan 17
LIT9:36 amLittle Rock
6h 53m
1 stop
MDW4:29 pmChicago Midway
Jan 24
MDW6:25 amChicago Midway
4h 29m
1 stop
LIT10:54 amLittle Rock
$229
Find similar
Delta
Apr 25
LIT12:12 pmLittle Rock
4h 24m
1 stop
MDW4:36 pmChicago Midway
May 1
MDW5:31 pmChicago Midway
6h 08m
1 stop
LIT11:39 pmLittle Rock
$268
Find similar
Delta
Mar 1
LIT5:25 amLittle Rock
4h 29m
1 stop
MDW9:54 amChicago Midway
Mar 4
MDW6:40 pmChicago Midway
4h 56m
1 stop
LIT11:36 pmLittle Rock
$307
Find similar

Southwest flights from Little Rock to Chicago Midway Airport

Our best Southwest deals on Little Rock to Chicago Midway Airport flight tickets
Southwest
Jan 21
LIT6:15 amLittle Rock
3h 15m
1 stop
MDW9:30 amChicago Midway
Jan 28
MDW1:15 pmChicago Midway
7h 55m
2 stops
LIT9:10 pmLittle Rock
$264
Find similar
Southwest
Jan 31
LIT12:40 pmLittle Rock
7h 50m
1 stop
MDW8:30 pmChicago Midway
Feb 1
MDW5:20 amChicago Midway
4h 45m
1 stop
LIT10:05 amLittle Rock
$283
Find similar
Southwest
Jan 21
LIT9:05 amLittle Rock
7h 40m
2 stops
MDW4:45 pmChicago Midway
Jan 28
MDW1:15 pmChicago Midway
7h 55m
2 stops
LIT9:10 pmLittle Rock
$285
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 December 23, 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

Sat 1/17

9:36 am-4:29 pm

1 stop6h 53m

Chicago Midway

Sat 1/24

6:25 am-10:54 am

1 stop4h 29m

$229

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 1/21

6:15 am-9:30 am

1 stop3h 15m

Chicago Midway

Wed 1/28

1:15 pm-9:10 pm

2 stops7h 55m

$264

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Sat 4/25

12:12 pm-4:36 pm

1 stop4h 24m

Chicago Midway

Fri 5/1

5:31 pm-11:39 pm

1 stop6h 08m

$268

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Sat 1/31

12:40 pm-8:30 pm

1 stop7h 50m

Chicago Midway

Sun 2/1

5:20 am-10:05 am

1 stop4h 45m

$283

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Wed 1/21

9:05 am-4:45 pm

2 stops7h 40m

Chicago Midway

Wed 1/28

1:15 pm-9:10 pm

2 stops7h 55m

$285

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Sat 1/31

5:40 am-4:25 pm

2 stops10h 45m

Chicago Midway

Sun 2/1

5:20 am-10:05 am

1 stop4h 45m

$294

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Sat 1/17

6:35 am-11:35 am

1 stop5h 00m

Chicago Midway

Sat 1/24

6:00 am-2:50 pm

2 stops8h 50m

$296

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Fri 1/9

3:58 pm-10:07 pm

1 stop6h 09m

Chicago Midway

Sun 1/11

5:31 pm-11:38 pm

1 stop6h 07m

$304

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Sun 3/1

5:25 am-9:54 am

1 stop4h 29m

Chicago Midway

Wed 3/4

6:40 pm-11:36 pm

1 stop4h 56m

$307

Little RockChicago

LIT - MDW

LITMDW

Little Rock

Sat 1/31

5:40 am-4:25 pm

2 stops10h 45m

Chicago Midway

Sun 2/1

8:15 am-4:05 pm

2 stops7h 50m

$334

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 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 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

Fastest flight time

4h 24m

Direct flights

None
The fastest flight from Little Rock to Chicago Midway Airport takes 4h 24m
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

  • 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 24m.

  • 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 $261Free CancellationRating
8.0
4,253 reviews
Search Southwest flights

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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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