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Cheap flights from Little Rock to Chicago from $137

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 9/6. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Little Rock to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:25 pm - 11:25 pmLIT  Little Rock-MDW Chicago Midway
6h 00m1 stop Dallas Love Field
Southwest Logo
5:55 am - 9:10 amMDW  Chicago Midway-LIT Little Rock
3h 15m1 stop Nashville Intl
$273Southwest
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
3:05 pm - 8:10 pmLIT  Little Rock-MDW Chicago Midway
5h 05m1 stop Nashville Intl
Southwest Logo
5:30 am - 10:15 amMDW  Chicago Midway-LIT Little Rock
4h 45m1 stop Dallas Love Field
$273Southwest
Tue, Sep 8 - Mon, Sep 14
Southwest Logo
5:25 pm - 11:20 pmLIT  Little Rock-MDW Chicago Midway
5h 55m1 stop Dallas Love Field
Southwest Logo
5:55 am - 9:10 amMDW  Chicago Midway-LIT Little Rock
3h 15m1 stop Nashville Intl
$273Southwest
Fri, Aug 28 - Mon, Aug 31
Southwest Logo
5:25 pm - 11:20 pmLIT  Little Rock-MDW Chicago Midway
5h 55m1 stop Dallas Love Field
Southwest Logo
5:30 am - 10:15 amMDW  Chicago Midway-LIT Little Rock
4h 45m1 stop Dallas Love Field
$273Southwest
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
3:05 pm - 8:10 pmLIT  Little Rock-MDW Chicago Midway
5h 05m1 stop Nashville Intl
Southwest Logo
5:30 am - 10:15 amMDW  Chicago Midway-LIT Little Rock
4h 45m1 stop Dallas Love Field
$273Southwest
Tue, Sep 8 - Mon, Sep 14
Delta Logo
5:21 am - 11:51 amLIT  Little Rock-MDW Chicago Midway
6h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:51 pmMDW  Chicago Midway-LIT Little Rock
6h 46m1 stop Atlanta Hartsfield-Jackson
$274Delta
Tue, Aug 25 - Tue, Sep 1
Southwest Logo
9:50 am - 4:55 pmLIT  Little Rock-MDW Chicago Midway
7h 05m2 stops Dallas Love Field Memphis
Southwest Logo
5:30 am - 10:15 amMDW  Chicago Midway-LIT Little Rock
4h 45m1 stop Dallas Love Field
$278Southwest
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
2:40 pm - 9:55 pmLIT  Little Rock-MDW Chicago Midway
7h 15m2 stops Nashville Intl Lambert-St Louis
Southwest Logo
5:30 am - 10:15 amMDW  Chicago Midway-LIT Little Rock
4h 45m1 stop Dallas Love Field
$278Southwest
Fri, Aug 28 - Mon, Aug 31
Delta Logo
5:30 am - 10:33 amLIT  Little Rock-MDW Chicago Midway
5h 03m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 6:35 pmMDW  Chicago Midway-LIT Little Rock
5h 35m1 stop Atlanta Hartsfield-Jackson
$299Delta
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
1:25 pm - 7:20 pmLIT  Little Rock-MDW Chicago Midway
5h 55m1 stop Nashville Intl
Southwest Logo
2:25 pm - 7:20 pmMDW  Chicago Midway-LIT Little Rock
4h 55m1 stop Nashville Intl
$299Southwest
Sat, Aug 29 - Sat, Sep 5

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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
Sep 8
LIT3:05 pmLittle Rock
5h 05m
1 stop
MDW8:10 pmChicago Midway
Sep 14
MDW5:30 amChicago Midway
4h 45m
1 stop
LIT10:15 amLittle Rock
$273
Southwest
Aug 27
LIT9:50 amLittle Rock
7h 05m
2 stops
MDW4:55 pmChicago Midway
Aug 31
MDW5:30 amChicago Midway
4h 45m
1 stop
LIT10:15 amLittle Rock
$278
Southwest
Sep 1
LIT7:05 amLittle Rock
7h 10m
2 stops
MDW2:15 pmChicago Midway
Sep 8
MDW5:20 pmChicago Midway
4h 40m
1 stop
LIT10:00 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
Aug 25
LIT5:21 amLittle Rock
6h 30m
1 stop
MDW11:51 amChicago Midway
Sep 1
MDW6:05 amChicago Midway
6h 46m
1 stop
LIT12:51 pmLittle Rock
$274
Delta
Oct 23
LIT5:21 amLittle Rock
6h 29m
1 stop
MDW11:50 amChicago Midway
Oct 25
MDW6:04 amChicago Midway
5h 05m
1 stop
LIT11:09 amLittle Rock
$299
Delta
Aug 13
LIT5:21 amLittle Rock
4h 38m
1 stop
MDW9:59 amChicago Midway
Aug 16
MDW6:05 amChicago Midway
6h 46m
1 stop
LIT12:51 pmLittle Rock
$391

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 August 6, 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 Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Thu 9/24

5:25 pm-11:25 pm

1 stop6h 00m

Chicago Midway

Mon 9/28

5:55 am-9:10 am

1 stop3h 15m

$273

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Tue 9/8

3:05 pm-8:10 pm

1 stop5h 05m

Chicago Midway

Mon 9/14

5:30 am-10:15 am

1 stop4h 45m

$273
Quickest round-trip

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Fri 8/28

5:25 pm-11:20 pm

1 stop5h 55m

Chicago Midway

Mon 8/31

5:55 am-9:10 am

1 stop3h 15m

$273

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Thu 8/27

5:25 pm-11:20 pm

1 stop5h 55m

Chicago Midway

Mon 8/31

5:30 am-10:15 am

1 stop4h 45m

$273

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Tue 9/8

3:05 pm-8:10 pm

1 stop5h 05m

Chicago Midway

Mon 9/14

5:30 am-10:15 am

1 stop4h 45m

$273

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Tue 8/25

5:21 am-11:51 am

1 stop6h 30m

Chicago Midway

Tue 9/1

6:05 am-12:51 pm

1 stop6h 46m

$274

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Thu 8/27

9:50 am-4:55 pm

2 stops7h 05m

Chicago Midway

Mon 8/31

5:30 am-10:15 am

1 stop4h 45m

$278

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Fri 8/28

2:40 pm-9:55 pm

2 stops7h 15m

Chicago Midway

Mon 8/31

5:30 am-10:15 am

1 stop4h 45m

$278

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Thu 12/10

5:30 am-10:33 am

1 stop5h 03m

Chicago Midway

Mon 12/14

1:00 pm-6:35 pm

1 stop5h 35m

$299

Little RockChicago

LIT Little Rock - MDW Chicago Midway

LITMDW

Little Rock

Sat 8/29

1:25 pm-7:20 pm

1 stop5h 55m

Chicago Midway

Sat 9/5

2:25 pm-7:20 pm

1 stop4h 55m

$299

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 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 $267.

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 42m

Direct flights

None
The fastest flight from Little Rock to Chicago Midway Airport takes 4h 42m
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 42m.

  • 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
4,218 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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