Cheap Flight Tickets from Dallas (DAL) to Chicago (MDW), Starting at $280

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

$3980

WN Southwest Airlines • nonstop • 3h 30m

Jul 24 – Jul 27

The cheapest round trip flight from Dallas to Chicago (DAL-MDW-DAL) is currently $3980

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Cheapest Direct Flight

$3980

WN Southwest Airlines • nonstop • 3h 30m

Jul 24

The cheapest nonstop flight from Dallas to Chicago (DAL-MDW) is currently $3980

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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

WestJet Airlines

WestJet 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.

Jul 24 - Jul 27, Economy
WN
Dallas → Chicago
3h 30m
12:05 PM - 2:15 PM • nonstop
WN
Dallas → Chicago
3h 35m
11:00 AM - 1:15 PM • nonstop
$3980
Southwest Airlines
Jul 24 - Jul 27, Economy
WN
Dallas → Chicago
3h 35m
6:00 AM - 8:15 AM • nonstop
WN
Dallas → Chicago
3h 40m
6:40 AM - 9:00 AM • nonstop
$3980
Southwest Airlines
Jul 24 - Jul 27, Economy
WN
Dallas → Chicago
3h 35m
4:50 PM - 7:05 PM • nonstop
WN
Dallas → Chicago
3h 35m
6:25 PM - 8:40 PM • nonstop
$3980
Southwest Airlines
Jul 24 - Jul 27, Economy
WN
Dallas → Chicago
3h 35m
8:30 AM - 10:45 AM • nonstop
WN
Dallas → Chicago
3h 35m
8:40 PM - 10:55 PM • nonstop
$3980
Southwest Airlines
Jul 24 - Jul 27, Economy
WN
Dallas → Chicago
3h 35m
10:50 PM - 1:05 AM • nonstop
WN
Dallas → Chicago
6h 40m
2:05 PM - 6:05 PM • 1 stop
$4038
Southwest Airlines
Jul 24 - Jul 27, Economy
WN
Dallas → Chicago
3h 35m
2:05 PM - 4:20 PM • nonstop
WN
Dallas → Chicago
6h 40m
2:05 PM - 6:05 PM • 1 stop
$4038
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 WN : USD 4038
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 10:50 pm

Essential Information for Booking Flights from Dallas (DAL) - AI Insights

What's the cheapest airline from dal to mdw?
You can find budget-friendly flights from Dallas Love Field (DAL) to Chicago Midway International Airport (MDW) on Southwest Airlines. For a one-way trip, consider booking at least 30 days in advance to secure Low Fares. You can also look for Savings on airfares by visiting our website and using relevant keywords like "cheapestflights" or "cheapairline." Additionally, you can check for cost-effective options on our web agency.
What's the popular airline to fly from dal to mdw?
You can fly from Dallas Love Field (DAL) to Chicago Midway International Airport (MDW) on Southwest Airlines. This is a one-stop flight with 1 stop. Booking in advance will help you find cheaper airfares. You can check for available flights and fares on the fareleaders.com website.
What's the cheapest day of the week to fly from dal to mdw?
The cheapest day to fly from Dallas Love Field (DAL) to Chicago Midway International Airport (MDW) is Saturday. Flying on Saturdays can often result in lower fares, making it a budget-friendly option for your trip.
What's the cheapest month to fly from dal to mdw?
The cheapest month to fly from Dallas Love Field (DAL) to Chicago Midway International Airport (MDW) is November. Flying during this time can help you find budget-friendly flights. Consider booking your ticket in advance, as 30 days prior to departure can lead to savings on airfares.
Which airline/airlines fly from dal to mdw?
The airlines that fly from Dallas Love Field (DAL) to Chicago Midway International Airport (MDW) include WestJet Airlines, Southwest Airlines, Delta Airlines, American Airlines, United Airlines, and Frontier Airlines.
What is the estimated airfare for a one-way flight from Dallas Love Field to Chicago Midway International airport?
The estimated airfare for a one-way flight from Dallas Love Field to Chicago Midway International airport varies depending on the airline and time of booking, but with Southwest Airlines (WN) being the cheapest option, you can expect to pay around $200-$300 per person.
Can I book my flights directly on your website, agencia fareleaders.com, and what are the benefits of doing so?
Yes, you can book your flights directly on our website, and the benefits include exclusive discounts, easy booking process, and the ability to compare fares across multiple airlines.
How many advance booking days do I need to make to secure the best fares for my Milwaukee trip?
To secure the best fares for your Milwaukee trip, we recommend booking at least 30 advance booking days in advance, as this allows us to offer you the cheapest available options.
What is the policy on changing or cancelling flights if I need a vuelta (return) ticket?
If you need a vuelta (return) ticket, our policy allows for changes and cancellations up to 24 hours prior to departure, with no additional fees applied.
Are there any additional fees for checking in luggage or printing boarding passes on your website?
No, there are no additional fees for checking in luggage or printing boarding passes on our website. However, please note that some airlines may charge extra for these services.
Can I book flights with airlines other than those listed on your website, and what are the options?
Yes, you can book flights with airlines other than those listed on our website, but we offer exclusive discounts and deals on our partner airlines, including WestJet Airlines (WS) and Frontier Airlines (F9).
How do I know which cabin type is best for my needs, economy or business class?
To determine which cabin type is best for your needs, consider factors such as budget, travel dates, and personal preferences. Our website offers a comparison tool to help you choose the best cabin type for your Milwaukee trip.

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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