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Cheap flights from Chicago Midway Airport to Dallas from $53

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 11/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Dallas

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 5:59 pmMDW-DFW
11h 59m1 stop
Frontier Logo
7:05 pm - 9:28 pmDFW-MDW
2h 23mnonstop
$96Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
5:20 pm - 8:01 pmMDW-DFW
2h 41mnonstop
Frontier Logo
9:00 am - 9:22 pmDFW-MDW
12h 22m1 stop
$97Frontier
Find Deal
Sat, Oct 25 - Sat, Nov 1
Frontier Logo
9:34 pm - 12:12 amMDW-DFW
2h 38mnonstop
Frontier Logo
5:30 am - 11:30 amDFW-MDW
6h 00m1 stop
$98Frontier
Find Deal
Thu, Nov 6 - Thu, Nov 13
Frontier Logo
6:15 pm - 8:59 pmMDW-DFW
2h 44mnonstop
Frontier Logo
9:10 am - 11:30 amDFW-MDW
2h 20mnonstop
$99Frontier
Find Deal
Thu, Nov 20 - Sun, Nov 23
Frontier Logo
3:27 pm - 6:09 pmMDW-DFW
2h 42mnonstop
Frontier Logo
7:05 pm - 9:28 pmDFW-MDW
2h 23mnonstop
$100Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
6:15 am - 5:55 pmMDW-DFW
11h 40m1 stop
Multiple Airlines Logo
5:35 am - 11:30 amDFW-MDW
5h 55m1 stop
$146Multiple Airlines
Find Deal
Mon, Nov 10 - Mon, Nov 17
Southwest Logo
6:55 am - 9:10 amMDW-DAL
2h 15mnonstop
Southwest Logo
6:50 pm - 9:00 pmDAL-MDW
2h 10mnonstop
$151Southwest
Find Deal
Fri, Oct 31 - Tue, Nov 4
Southwest Logo
5:00 am - 7:30 amMDW-DAL
2h 30mnonstop
Southwest Logo
6:50 pm - 9:00 pmDAL-MDW
2h 10mnonstop
$157Southwest
Find Deal
Tue, Nov 11 - Wed, Nov 12
Delta Logo
5:34 pm - 11:52 pmMDW-DAL
6h 18m1 stop
Delta Logo
6:40 pm - 11:40 pmDAL-MDW
5h 00m1 stop
$197Delta
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Tue, Nov 11 - Wed, Nov 19
Delta Logo
6:00 am - 10:54 amMDW-DAL
4h 54m1 stop
Delta Logo
6:40 pm - 11:40 pmDAL-MDW
5h 00m1 stop
$198Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15

Frontier flights from Chicago Midway Airport to Dallas

Our best Frontier deals on Chicago Midway Airport to Dallas flight tickets
Frontier
Dec 4
MDW6:00 amChicago Midway
11h 59m
1 stop
DFW5:59 pmDallas/Fort Worth
Dec 7
DFW7:05 pmDallas/Fort Worth
2h 23m
MDW9:28 pmChicago Midway
$96
Find similar
Frontier
Oct 25
MDW5:20 pmChicago Midway
2h 41m
DFW8:01 pmDallas/Fort Worth
Nov 1
DFW9:00 amDallas/Fort Worth
12h 22m
1 stop
MDW9:22 pmChicago Midway
$97
Find similar
Frontier
Nov 6
MDW9:34 pmChicago Midway
2h 38m
DFW12:12 amDallas/Fort Worth
Nov 13
DFW5:30 amDallas/Fort Worth
6h 00m
1 stop
MDW11:30 amChicago Midway
$98
Find similar

Southwest flights from Chicago Midway Airport to Dallas

Our best Southwest deals on Chicago Midway Airport to Dallas flight tickets
Southwest
Oct 31
MDW6:55 amChicago Midway
2h 15m
DAL9:10 amDallas Love Field
Nov 4
DAL6:50 pmDallas Love Field
2h 10m
MDW9:00 pmChicago Midway
$151
Find similar
Southwest
Nov 11
MDW5:00 amChicago Midway
2h 30m
DAL7:30 amDallas Love Field
Nov 12
DAL6:50 pmDallas Love Field
2h 10m
MDW9:00 pmChicago Midway
$157
Find similar
Southwest
Nov 24
MDW5:15 pmChicago Midway
5h 35m
1 stop
DAL10:50 pmDallas Love Field
Dec 18
DAL7:50 pmDallas Love Field
2h 10m
MDW10:00 pmChicago Midway
$161
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Dallas 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 October 13, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Dallas that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 12/4

6:00 am-5:59 pm

1 stop11h 59m

Dallas/Fort Worth

Sun 12/7

7:05 pm-9:28 pm

Nonstop2h 23m

$96

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sat 10/25

5:20 pm-8:01 pm

Nonstop2h 41m

Dallas/Fort Worth

Sat 11/1

9:00 am-9:22 pm

1 stop12h 22m

$97

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 11/6

9:34 pm-12:12 am

Nonstop2h 38m

Dallas/Fort Worth

Thu 11/13

5:30 am-11:30 am

1 stop6h 00m

$98

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 11/20

6:15 pm-8:59 pm

Nonstop2h 44m

Dallas/Fort Worth

Sun 11/23

9:10 am-11:30 am

Nonstop2h 20m

$99

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 12/4

3:27 pm-6:09 pm

Nonstop2h 42m

Dallas/Fort Worth

Sun 12/7

7:05 pm-9:28 pm

Nonstop2h 23m

$100

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Mon 11/10

6:15 am-5:55 pm

1 stop11h 40m

Dallas/Fort Worth

Mon 11/17

5:35 am-11:30 am

1 stop5h 55m

$146

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Fri 10/31

6:55 am-9:10 am

Nonstop2h 15m

Dallas Love Field

Tue 11/4

6:50 pm-9:00 pm

Nonstop2h 10m

$151

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Tue 11/11

5:00 am-7:30 am

Nonstop2h 30m

Dallas Love Field

Wed 11/12

6:50 pm-9:00 pm

Nonstop2h 10m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Tue 11/11

5:34 pm-11:52 pm

1 stop6h 18m

Dallas Love Field

Wed 11/19

6:40 pm-11:40 pm

1 stop5h 00m

$197

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 11/8

6:00 am-10:54 am

1 stop4h 54m

Dallas Love Field

Sat 11/15

6:40 pm-11:40 pm

1 stop5h 00m

$198

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 Dallas from

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

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?

If you are unable to visit Dallas during the month of October, then departing from Chicago Midway Airport during the month April is also very affordable. Most momondo users find prices during this month for around $194.

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

On average, the least expensive day to fly to Dallas from Chicago Midway Airport is on a Friday. momondo users have found tickets for Friday departures for as low as $248. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $475.

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

Flying to Dallas from Chicago Midway Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $257 when looking at flights departing in the evening. In the afternoon is when there is more demand to fly to Dallas, so prices are often more expensive at around $335 per ticket.

What is the cheapest Chicago Midway to Dallas flight route?

Fly from Chicago Midway to Dallas/Fort Worth for the best Chicago Midway - Dallas flight prices

How far in advance should I book a flight to Dallas?

You are more likely to see cheaper flights to Dallas from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Dallas for around $208 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Dallas from Chicago Midway Airport for as low as $145 on momondo.

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

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

Cheap Chicago Midway Airport to Dallas flight deals and tips

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

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Dallas

2 airports
The fastest flight from Chicago Midway Airport to Dallas takes 2h 15m
Direct flights go from Chicago Midway Airport to Dallas every day.
There are 2 airports near Dallas: Dallas/Fort Worth (DFW), Dallas Love Field (DAL)
Search flight deals

  • How far is Chicago Midway to Dallas by plane?

    Dallas is 795.4 mi away from Chicago Midway. By plane, this route typically takes 2h 15m.

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

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

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

  • How old do you have to be to fly from Chicago Midway Airport to Dallas?

    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.

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

    The travel and health documents required for your trip to Dallas can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Dallas. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago Midway Airport to Dallas

Compare and see reviews for airlines that fly from Chicago Midway Airport to Dallas with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $74Free CancellationRating
5.8
3,136 reviews
Search Frontier flights
SouthwestPriceFrom $147Free CancellationRating
8.0
4,235 reviews
Search Southwest flights

Why use momondo?

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

Finding the right flight to Dallas from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Dallas quick and easy, saving you time and money.

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?

momondo provides multiple filters to help you find the best flight to Dallas from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Dallas right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Dallas from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Dallas

Airports listed have a maximum distance of 15.5 mi from Dallas
Dallas Love Field Airport
Dallas/Fort Worth Airport