Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Dallas from $66

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Dallas departing on 2/14. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Dallas

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:00 pm - 10:25 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
5:30 pm - 7:45 pm
DAL
-
MDW
2h 15mnonstop
$145Southwest
Wed, Jan 14 - Sat, Jan 17
Southwest Logo
12:00 pm - 2:30 pm
MDW
-
DAL
2h 30mnonstop
Southwest Logo
5:30 pm - 7:45 pm
DAL
-
MDW
2h 15mnonstop
$147Southwest
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
12:00 pm - 2:30 pm
MDW
-
DAL
2h 30mnonstop
Southwest Logo
10:25 am - 12:35 pm
DAL
-
MDW
2h 10mnonstop
$157Southwest
Sat, Jan 31 - Wed, Feb 4
Southwest Logo
4:20 pm - 6:45 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
8:40 pm - 10:50 pm
DAL
-
MDW
2h 10mnonstop
$159Southwest
Sat, Feb 21 - Sat, Feb 28
Southwest Logo
3:55 pm - 7:35 pm
MDW
-
DAL
3h 40m1 stop
Southwest Logo
11:20 am - 1:30 pm
DAL
-
MDW
2h 10mnonstop
$163Southwest
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
8:00 pm - 10:25 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
12:55 pm - 4:25 pm
DAL
-
MDW
3h 30m1 stop
$164Southwest
Wed, Jan 14 - Sat, Jan 17
Southwest Logo
12:00 pm - 2:30 pm
MDW
-
DAL
2h 30mnonstop
Southwest Logo
12:55 pm - 4:25 pm
DAL
-
MDW
3h 30m1 stop
$166Southwest
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
8:00 pm - 10:25 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
6:30 pm - 8:40 pm
DAL
-
MDW
2h 10mnonstop
$168Southwest
Wed, Jan 14 - Wed, Jan 21
Southwest Logo
4:20 pm - 6:45 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
7:00 pm - 11:30 pm
DAL
-
MDW
4h 30m1 stop
$169Southwest
Sat, Feb 21 - Sat, Feb 28
Southwest Logo
4:20 pm - 6:45 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
4:50 pm - 7:00 pm
DAL
-
MDW
2h 10mnonstop
$170Southwest
Sat, Feb 28 - Tue, Mar 3

Southwest flights from Chicago Midway Airport to Dallas Love Field Airport

Our best Southwest deals on Chicago Midway Airport to Dallas Love Field Airport flight tickets
Southwest
Feb 21
MDW4:20 pmChicago Midway
2h 25m
DAL6:45 pmDallas Love Field
Feb 28
DAL8:40 pmDallas Love Field
2h 10m
MDW10:50 pmChicago Midway
$157
Find similar
Southwest
Feb 21
MDW4:20 pmChicago Midway
2h 25m
DAL6:45 pmDallas Love Field
Feb 28
DAL8:40 pmDallas Love Field
2h 10m
MDW10:50 pmChicago Midway
$159
Find similar
Southwest
Jan 17
MDW3:55 pmChicago Midway
3h 40m
1 stop
DAL7:35 pmDallas Love Field
Jan 24
DAL11:20 amDallas Love Field
2h 10m
MDW1:30 pmChicago Midway
$163
Find similar

Delta flights from Chicago Midway Airport to Dallas Love Field Airport

Our best Delta deals on Chicago Midway Airport to Dallas Love Field Airport flight tickets
Delta
Jan 17
MDW11:21 amChicago Midway
6h 26m
1 stop
DAL5:47 pmDallas Love Field
Jan 20
DAL6:00 amDallas Love Field
5h 59m
1 stop
MDW11:59 amChicago Midway
$177
Find similar
Delta
Jan 24
MDW4:30 pmChicago Midway
5h 59m
1 stop
DAL10:29 pmDallas Love Field
Jan 29
DAL6:00 amDallas Love Field
5h 59m
1 stop
MDW11:59 amChicago Midway
$195
Find similar
Delta
Feb 19
MDW10:49 amChicago Midway
7h 00m
1 stop
DAL5:49 pmDallas Love Field
Feb 23
DAL11:58 amDallas Love Field
5h 47m
1 stop
MDW5:45 pmChicago Midway
$213
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Dallas Love Field 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 22, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Dallas Love Field Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 1/14

8:00 pm-10:25 pm

Nonstop2h 25m

Dallas Love Field

Sat 1/17

5:30 pm-7:45 pm

Nonstop2h 15m

$145

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 1/10

12:00 pm-2:30 pm

Nonstop2h 30m

Dallas Love Field

Sat 1/17

5:30 pm-7:45 pm

Nonstop2h 15m

$147

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 1/31

12:00 pm-2:30 pm

Nonstop2h 30m

Dallas Love Field

Wed 2/4

10:25 am-12:35 pm

Nonstop2h 10m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 2/21

4:20 pm-6:45 pm

Nonstop2h 25m

Dallas Love Field

Sat 2/28

8:40 pm-10:50 pm

Nonstop2h 10m

$159

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 1/17

3:55 pm-7:35 pm

1 stop3h 40m

Dallas Love Field

Sat 1/24

11:20 am-1:30 pm

Nonstop2h 10m

$163

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 1/14

8:00 pm-10:25 pm

Nonstop2h 25m

Dallas Love Field

Sat 1/17

12:55 pm-4:25 pm

1 stop3h 30m

$164

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 1/10

12:00 pm-2:30 pm

Nonstop2h 30m

Dallas Love Field

Sat 1/17

12:55 pm-4:25 pm

1 stop3h 30m

$166

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 1/14

8:00 pm-10:25 pm

Nonstop2h 25m

Dallas Love Field

Wed 1/21

6:30 pm-8:40 pm

Nonstop2h 10m

$168

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 2/21

4:20 pm-6:45 pm

Nonstop2h 25m

Dallas Love Field

Sat 2/28

7:00 pm-11:30 pm

1 stop4h 30m

$169

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 2/28

4:20 pm-6:45 pm

Nonstop2h 25m

Dallas Love Field

Tue 3/3

4:50 pm-7:00 pm

Nonstop2h 10m

$170

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Dallas from

How to get the cheapest flight ticket from Chicago Midway Airport to Dallas Love Field 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 Dallas Love Field Airport?

If you aren’t able to travel to Dallas Love Field Airport during the month of April, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $206.

What is the cheapest day to depart on your flight to Dallas Love Field Airport?

According to our data, Wednesday is the cheapest day to fly to Dallas Love Field Airport from Chicago Midway Airport. The lowest ticket price found for a Wednesday departure recently was $245. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to Dallas Love Field Airport is Sunday, with ticket prices averaging around $401.

What is the cheapest time of day to depart on your flight to Dallas Love Field Airport?

In the evening is the cheapest time of day to fly from Chicago Midway Airport to Dallas Love Field Airport when you can find flight prices for as low as $226. Flying to Dallas Love Field Airport in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Dallas Love Field Airport, so prices are often more expensive at around $302 per ticket.

What is the cheapest Chicago Midway to Dallas Love Field flight route?

Fly from Chicago Midway to Dallas Love Field for the best Chicago Midway - Dallas Love Field flight prices

What cabin class options are available on Chicago Midway to Dallas Love Field flights?

There is only 1 cabin class available to choose from on Chicago Midway to Dallas Love Field flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Dallas Love Field Airport flights?

You could potentially save up to 8% on your flight if you consider stops on a Chicago Midway Airport to Dallas Love Field Airport flight.

When to book flights from Chicago Midway Airport to Dallas Love Field Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Dallas Love Field Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Dallas Love Field Airport (MDW to DAL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Dallas Love Field Airport

Best Price Found

$163

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Dallas Love Field Airport from Chicago Midway Airport in the past 72 hours is $163. The best round-trip flight deal from Chicago Midway Airport to Dallas Love Field Airport found on momondo in the last 72 hours is $252.
The fastest flight from Chicago Midway Airport to Dallas Love Field Airport takes 2h 20m
Direct flights go from Chicago Midway Airport to Dallas Love Field Airport every day.
Search flight deals

  • How far is Chicago Midway to Dallas Love Field by plane?

    The straight-line distance from Chicago Midway to Dallas Love Field is 793.4 mi. Flights usually cover this in 2h 20m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Dallas Love Field Airport?

    Prices for flights from Chicago Midway Airport to Dallas Love Field Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Dallas Love Field Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Dallas Love Field 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 Chicago Midway Airport to Dallas Love Field Airport.

  • What documentation or ID do you need to fly to Dallas Love Field Airport?

    The travel and health documents you'll need for your trip to Dallas Love Field Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Dallas Love Field Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Dallas Love Field Airport?

  • What is the most popular airline from Chicago Midway Airport to Dallas Love Field Airport?

Best airlines flying from Chicago Midway Airport to Dallas Love Field Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Dallas Love Field Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $86Free CancellationRating
5.8
3,076 reviews
Search Frontier flights
SouthwestPriceFrom $147Free CancellationRating
8.0
4,253 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Dallas Love Field Airport

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to Dallas Love Field Airport, operating 44 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Dallas Love Field Airport starts from $147 round-trip, up to an average price of $285. Our users have rated Southwest at 8.0/10.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Dallas?

It is quick and easy to find Chicago to Dallas flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Dallas that suits you.

Can I find flights from Chicago to Dallas with flexible booking policies on momondo?

Flights from Chicago to Dallas with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Dallas?

Once all potential Chicago to Dallas 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 Chicago to Dallas right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Dallas now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Dallas and let you know when they change.

An easier way to manage your Dallas Love Field Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 1/21
Wed 1/28
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Dallas