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Cheap flights from Dallas Love Field Airport to Chicago from $139

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Dallas Love Field Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:15 am - 9:30 amDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
7:15 am - 9:30 amMDW  Chicago Midway-DAL Dallas Love Field
2h 15mnonstop
$277Southwest
Wed, Oct 21 - Mon, Oct 26
Southwest Logo
10:55 pm - 1:10 amDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$277Southwest
Thu, Nov 12 - Mon, Nov 16
Southwest Logo
9:35 pm - 11:50 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
5:20 am - 7:45 amMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
$277Southwest
Wed, Oct 28 - Mon, Nov 2
Southwest Logo
8:05 pm - 10:20 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
10:55 am - 1:25 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$277Southwest
Wed, Oct 28 - Wed, Nov 4
Southwest Logo
6:40 am - 8:50 amDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
6:20 pm - 8:55 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 35mnonstop
$277Southwest
Mon, Nov 2 - Sat, Nov 7
Southwest Logo
6:25 pm - 8:40 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
6:00 am - 8:15 amMDW  Chicago Midway-DAL Dallas Love Field
2h 15mnonstop
$277Southwest
Tue, Oct 27 - Sat, Oct 31
Southwest Logo
5:40 pm - 7:55 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
7:05 am - 9:35 amMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$277Southwest
Mon, Dec 7 - Wed, Dec 9
Southwest Logo
11:55 am - 2:10 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
7:05 am - 9:35 amMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$277Southwest
Thu, Oct 29 - Tue, Nov 3
Delta Logo
3:59 pm - 10:33 pmDAL  Dallas Love Field-MDW Chicago Midway
6h 34m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:49 pm - 6:05 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 16m1 stop Atlanta Hartsfield-Jackson
$297Delta
Sat, Oct 24 - Tue, Oct 27
Delta Logo
6:06 am - 12:04 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:02 pm - 6:06 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 04m1 stop Atlanta Hartsfield-Jackson
$297Delta
Wed, Dec 9 - Tue, Dec 15

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Delta flights from Dallas Love Field Airport to Chicago

Our best Delta deals on Dallas Love Field Airport to Chicago flight tickets
Delta
Oct 20
DAL3:59 pmDallas Love Field
7h 58m
1 stop
ORD11:57 pmChicago O'Hare Intl
Oct 31
ORD8:05 amChicago O'Hare Intl
6h 06m
1 stop
DAL2:11 pmDallas Love Field
$297
Delta
Oct 21
DAL6:12 amDallas Love Field
10h 20m
2 stops
ORD4:32 pmChicago O'Hare Intl
Oct 27
ORD3:40 pmChicago O'Hare Intl
6h 59m
1 stop
DAL10:39 pmDallas Love Field
$302
Delta
Dec 4
DAL6:54 pmDallas Love Field
5h 02m
1 stop
ORD11:56 pmChicago O'Hare Intl
Dec 8
ORD8:04 amChicago O'Hare Intl
6h 13m
1 stop
DAL2:17 pmDallas Love Field
$307

Southwest flights from Dallas Love Field Airport to Chicago

Our best Southwest deals on Dallas Love Field Airport to Chicago flight tickets
Southwest
Oct 24
DAL10:50 amDallas Love Field
2h 15m
MDW1:05 pmChicago Midway
Oct 26
MDW5:15 amChicago Midway
2h 15m
DAL7:30 amDallas Love Field
$277
Southwest
Oct 24
DAL11:35 amDallas Love Field
3h 45m
1 stop
MDW3:20 pmChicago Midway
Oct 26
MDW5:15 amChicago Midway
2h 15m
DAL7:30 amDallas Love Field
$283
Southwest
Oct 22
DAL10:55 pmDallas Love Field
2h 15m
MDW1:10 amChicago Midway
Oct 23
MDW9:20 pmChicago Midway
2h 10m
DAL11:30 pmDallas Love Field
$287

momondo Fare Finder

 
Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago that are best for you.

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Route

Depart

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Price

Cheapest round-trip
Quickest round-trip

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Wed 10/21

7:15 am-9:30 am

Nonstop2h 15m

Chicago Midway

Mon 10/26

7:15 am-9:30 am

Nonstop2h 15m

$277

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Thu 11/12

10:55 pm-1:10 am

Nonstop2h 15m

Chicago Midway

Mon 11/16

8:45 pm-11:15 pm

Nonstop2h 30m

$277

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Wed 10/28

9:35 pm-11:50 pm

Nonstop2h 15m

Chicago Midway

Mon 11/2

5:20 am-7:45 am

Nonstop2h 25m

$277

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Wed 10/28

8:05 pm-10:20 pm

Nonstop2h 15m

Chicago Midway

Wed 11/4

10:55 am-1:25 pm

Nonstop2h 30m

$277

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Mon 11/2

6:40 am-8:50 am

Nonstop2h 10m

Chicago Midway

Sat 11/7

6:20 pm-8:55 pm

Nonstop2h 35m

$277

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Tue 10/27

6:25 pm-8:40 pm

Nonstop2h 15m

Chicago Midway

Sat 10/31

6:00 am-8:15 am

Nonstop2h 15m

$277

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Mon 12/7

5:40 pm-7:55 pm

Nonstop2h 15m

Chicago Midway

Wed 12/9

7:05 am-9:35 am

Nonstop2h 30m

$277

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Thu 10/29

11:55 am-2:10 pm

Nonstop2h 15m

Chicago Midway

Tue 11/3

7:05 am-9:35 am

Nonstop2h 30m

$277

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Sat 10/24

3:59 pm-10:33 pm

1 stop6h 34m

Chicago Midway

Tue 10/27

12:49 pm-6:05 pm

1 stop5h 16m

$297

DallasChicago

DAL Dallas Love Field - MDW Chicago Midway

DALMDW

Dallas Love Field

Wed 12/9

6:06 am-12:04 pm

1 stop5h 58m

Chicago Midway

Tue 12/15

1:02 pm-6:06 pm

1 stop5h 04m

$297

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 Love Field Airport to Chicago

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 typical price of a round-trip flight between Dallas Love Field Airport and Chicago?

Prices are currently typical for flights on this route.

Typical prices usually range from $277 to $385.
The lowest price recently found on this route was $277.

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Dallas Love Field Airport, with most prices found around $198. If you’re not able to fly to Chicago in January, then December is your next best option. Flight prices from Dallas Love Field Airport to Chicago during December average around $225.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $310. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Dallas Love Field Airport to Chicago for around $543.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Dallas Love Field Airport to Chicago during this time can be as low as $289. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $441.

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

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

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

There is only 1 cabin class available to choose from on Dallas Love Field Airport to Chicago 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 Dallas Love Field Airport to Chicago flights?

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

When to book flights from Dallas Love Field Airport to Chicago

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

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

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

Best Price Found

$139

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Dallas Love Field Airport in the past 72 hours is $139. The best round-trip flight deal from Dallas Love Field Airport to Chicago found on momondo in the last 72 hours is $277.
The fastest flight from Dallas Love Field Airport to Chicago takes 2h 10m
Direct flights go from Dallas Love Field Airport to Chicago every day.
There are 3 airports in Chicago. From Dallas Love Field Airport there are direct flights to Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Dallas Love Field Airport to Chicago

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

    There are 802.0 mi between Dallas Love Field and Chicago. 2h 10m is a normal flight duration for this route.

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

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

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Dallas Love Field Airport to Chicago.

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

    The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 Dallas Love Field Airport to Chicago?

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

Best airlines flying from Dallas Love Field Airport to Chicago

Compare and see reviews for airlines that fly from Dallas Love Field Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $175Free CancellationRating
8.0
4,201 reviews
Search Southwest flights

  • Southwest Flights From Dallas Love Field Airport to Chicago

    Southwest flight deals from Dallas Love Field Airport to Chicago start from $175 round-trip. Over the 9 Southwest flights for this route in a normal week, average airfare is usually $359 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

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

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Dallas to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Dallas to Chicago 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 Dallas to Chicago?

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Dallas and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport