Cheap Flight Tickets from Dallas (DAL) to Chicago (MDW), Starting at $67

Good to Know: Cheapest and Fastest DAL - MDW Flights

Useful information for finding best airline tickets from Dallas Love Field to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$603

WN Southwest Airlines • 1 stop • 15h 35m

Oct 05 – Oct 05

The cheapest round trip flight from Dallas to Chicago (DAL-MDW-DAL) is currently $603

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Cheapest One way Flight

$67

WN Southwest Airlines • 2 stops • 18h 40m

Oct 10

The cheapest one way flight from Dallas to Chicago (DAL-MDW) is currently $67

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Cheapest Direct Flight

$419

WN Southwest Airlines • nonstop • 3h 35m

Nov 13

The cheapest nonstop flight from Dallas to Chicago (DAL-MDW) is currently $419

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Fastest Flight

3h 30m

The fastest nonstop flight from Dallas to Chicago (DAL-MDW) takes 3h 30m

Top Airlines Flying from Dallas to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Latest Flight Deals from Dallas (DAL) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Dallas to Chicago. Ideal for travelers with confirmed return itineraries.

Oct 05 - Oct 05, Economy
WN
Dallas → Chicago
15h 35m
6:00 AM - 3:35 PM • 1 stop
WN
Dallas → Chicago
3h 35m
8:00 PM - 10:15 PM • nonstop
$603
Southwest Airlines
Oct 05 - Oct 05, Economy
WN
Dallas → Chicago
15h 45m
7:30 AM - 5:15 PM • 1 stop
WN
Dallas → Chicago
3h 30m
9:20 PM - 11:30 PM • nonstop
$603
Southwest Airlines
Oct 05 - Oct 05, Economy
WN
Dallas → Chicago
15h 35m
6:00 AM - 3:35 PM • 2 stops
WN
Dallas → Chicago
3h 35m
8:00 PM - 10:15 PM • nonstop
$608
Southwest Airlines
Oct 05 - Oct 05, Economy
WN
Dallas → Chicago
7h 10m
7:30 AM - 12:00 PM • 1 stop
WN
Dallas → Chicago
14h
10:15 PM - 6:55 AM • 1 stop
$612
Southwest Airlines
Oct 05 - Oct 05, Economy
WN
Dallas → Chicago
7h 5m
7:30 AM - 11:55 AM • 1 stop
WN
Dallas → Chicago
9h
5:50 PM - 11:30 PM • 1 stop
$612
Southwest Airlines
Oct 05 - Oct 05, Economy
WN
Dallas → Chicago
9h 10m
6:05 AM - 11:55 AM • 1 stop
WN
Dallas → Chicago
5h 30m
5:50 PM - 9:20 PM • 1 stop
$635
Southwest Airlines

Fly from Dallas to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Dallas to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Dallas to Chicago Flights

What are the airports in Dallas?
DAL
What’s the most popular airline flying from DAL to MDW?
The most popular airline flying from Dallas to Chicago are
Can I fly from DAL to MDW non-stop?
Yes, you can fly DAL to MDW non-stop on
Which airlines fly nonstop between Dallas and Chicago?
The non-stop flights between Dallas and Chicago are .
What’s the earliest departure time from DAL to MDW Airport?
The earliest flight leaves DAL at 6:00 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Dallas to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from DAL to MDW?
Read the fare rules of the Dallas to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Dallas and Chicago?
operate flights between Dallas and Chicago
How long does a flight from Dallas to Chicago take?
It takes approximately 2 hour to fly non-stop from DAL to MDW, which is 793.47 miles by air.
Which airlines provide the cheapest flights from Dallas (DAL) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from DAL were found on AA : USD 288
Do I need a passport to fly between DAL and MDW?
No
What’s the latest departure time from DAL to MDW ?
The last flight leaves DAL at 10:55 pm

Dallas (DAL) to Chicago (MDW): Airport Information

Origin Airport Dallas Love Field, Dallas, US
Destination Airport Chicago Midway International , Chicago, US
Distance 793 miles

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