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Cheap flights from Dallas to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Dallas to Chicago departing on 11/29. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
10:48 pm - 1:05 amDFW-MDW
2h 17mnonstop
Frontier Logo
5:30 am - 8:15 amMDW-DFW
2h 45mnonstop
$92Frontier
Find Deal
Fri, Nov 21 - Sun, Nov 23
Frontier Logo
11:47 am - 2:04 pmDFW-MDW
2h 17mnonstop
Frontier Logo
8:05 am - 10:47 amMDW-DFW
2h 42mnonstop
$93Frontier
Find Deal
Thu, Dec 11 - Sun, Dec 14
Frontier Logo
10:10 am - 8:45 pmDFW-MDW
10h 35m1 stop
Frontier Logo
7:00 am - 9:52 amMDW-DFW
2h 52mnonstop
$94Frontier
Find Deal
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
11:47 am - 2:04 pmDFW-MDW
2h 17mnonstop
Frontier Logo
12:35 pm - 3:05 pmMDW-DFW
2h 30mnonstop
$96Frontier
Find Deal
Fri, Dec 12 - Mon, Dec 15
Frontier Logo
5:35 am - 11:30 amDFW-MDW
5h 55m1 stop
Frontier Logo
5:30 am - 8:15 amMDW-DFW
2h 45mnonstop
$98Frontier
Find Deal
Mon, Nov 17 - Thu, Nov 20
Frontier Logo
9:54 pm - 12:13 amDFW-MDW
2h 19mnonstop
Frontier Logo
6:15 pm - 8:59 pmMDW-DFW
2h 44mnonstop
$101Frontier
Find Deal
Sun, Nov 23 - Thu, Nov 27
Southwest Logo
4:50 pm - 7:00 pmDAL-MDW
2h 10mnonstop
Southwest Logo
4:25 pm - 6:55 pmMDW-DAL
2h 30mnonstop
$117Southwest
Find Deal
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
11:47 am - 2:04 pmDFW-MDW
2h 17mnonstop
Multiple Airlines Logo
6:00 am - 6:47 pmMDW-DFW
12h 47m1 stop
$120Multiple Airlines
Find Deal
Thu, Dec 4 - Sat, Dec 6
Southwest Logo
7:45 pm - 9:55 pmDAL-MDW
2h 10mnonstop
Southwest Logo
1:30 pm - 7:00 pmMDW-DAL
5h 30m1 stop
$123Southwest
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Fri, Jan 16 - Sun, Jan 18
Southwest Logo
2:50 pm - 5:05 pmDAL-MDW
2h 15mnonstop
Southwest Logo
5:25 am - 10:15 amMDW-DAL
4h 50m1 stop
$127Southwest
Find Deal
Sat, Feb 14 - Tue, Feb 17

Southwest flights from Dallas to Chicago Midway Airport

Our best Southwest deals on Dallas to Chicago Midway Airport flight tickets
Southwest
Jan 9
DAL4:50 pmDallas Love Field
2h 10m
MDW7:00 pmChicago Midway
Jan 12
MDW4:25 pmChicago Midway
2h 30m
DAL6:55 pmDallas Love Field
$117
Find similar
Southwest
Jan 16
DAL7:45 pmDallas Love Field
2h 10m
MDW9:55 pmChicago Midway
Jan 18
MDW1:30 pmChicago Midway
5h 30m
1 stop
DAL7:00 pmDallas Love Field
$123
Find similar
Southwest
Feb 14
DAL2:50 pmDallas Love Field
2h 15m
MDW5:05 pmChicago Midway
Feb 17
MDW5:25 amChicago Midway
4h 50m
1 stop
DAL10:15 amDallas Love Field
$127
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Frontier flights from Dallas to Chicago Midway Airport

Our best Frontier deals on Dallas to Chicago Midway Airport flight tickets
Frontier
Nov 21
DFW10:48 pmDallas/Fort Worth
2h 17m
MDW1:05 amChicago Midway
Nov 23
MDW5:30 amChicago Midway
2h 45m
DFW8:15 amDallas/Fort Worth
$92
Find similar
Frontier
Dec 11
DFW11:47 amDallas/Fort Worth
2h 17m
MDW2:04 pmChicago Midway
Dec 14
MDW8:05 amChicago Midway
2h 42m
DFW10:47 amDallas/Fort Worth
$93
Find similar
Frontier
Jan 15
DFW10:10 amDallas/Fort Worth
10h 35m
1 stop
MDW8:45 pmChicago Midway
Jan 18
MDW7:00 amChicago Midway
2h 52m
DFW9:52 amDallas/Fort Worth
$94
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Dallas 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 November 5, 2025.
Use the filters below to find and compare flights from Dallas to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 11/21

10:48 pm-1:05 am

Nonstop2h 17m

Chicago Midway

Sun 11/23

5:30 am-8:15 am

Nonstop2h 45m

$92

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 12/11

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Sun 12/14

8:05 am-10:47 am

Nonstop2h 42m

$93

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 1/15

10:10 am-8:45 pm

1 stop10h 35m

Chicago Midway

Sun 1/18

7:00 am-9:52 am

Nonstop2h 52m

$94

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 12/12

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Mon 12/15

12:35 pm-3:05 pm

Nonstop2h 30m

$96

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Mon 11/17

5:35 am-11:30 am

1 stop5h 55m

Chicago Midway

Thu 11/20

5:30 am-8:15 am

Nonstop2h 45m

$98

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sun 11/23

9:54 pm-12:13 am

Nonstop2h 19m

Chicago Midway

Thu 11/27

6:15 pm-8:59 pm

Nonstop2h 44m

$101

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 1/9

4:50 pm-7:00 pm

Nonstop2h 10m

Chicago Midway

Mon 1/12

4:25 pm-6:55 pm

Nonstop2h 30m

$117

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 12/4

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Sat 12/6

6:00 am-6:47 pm

1 stop12h 47m

$120

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 1/16

7:45 pm-9:55 pm

Nonstop2h 10m

Chicago Midway

Sun 1/18

1:30 pm-7:00 pm

1 stop5h 30m

$123

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 2/14

2:50 pm-5:05 pm

Nonstop2h 15m

Chicago Midway

Tue 2/17

5:25 am-10:15 am

1 stop4h 50m

$127

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 Dallas 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 Dallas, with most prices found around $168. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Dallas during the month September is also very affordable. Most momondo users find prices during this month for around $177.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Dallas. The lowest ticket price found for a Saturday departure recently was $152. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from Dallas because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $185.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Dallas at noon is the least expensive time of day to depart. momondo users have found prices as low as $196 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $221. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Dallas to Chicago Midway flight route?

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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Dallas when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $200 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Dallas for as low as $99 on momondo.

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

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

Cheap Dallas to Chicago Midway Airport flight deals and tips

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

Fastest flight time

2h 10m

Direct flights

Every day
The fastest flight from Dallas to Chicago Midway Airport takes 2h 10m
Direct flights go from Dallas to Chicago Midway Airport every day.
Search flight deals

  • How far is Dallas to Chicago Midway by plane?

    There are 795.4 mi between Dallas and Chicago Midway. Flights usually cover this in 2h 10m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Dallas to Chicago Midway Airport are refreshed on a daily basis.

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

  • How old do you have to be to fly from Dallas 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 Dallas 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.

Best airlines flying from Dallas to Chicago Midway Airport

Compare and see reviews for airlines that fly from Dallas to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $76Free CancellationRating
5.8
3,115 reviews
Search Frontier flights
SouthwestPriceFrom $147Free CancellationRating
8.0
4,239 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago from Dallas 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 Chicago quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Dallas to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Dallas.

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

Of course. momondo tracks the price of Dallas to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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