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Cheap flights from Dallas Love Field Airport to Chicago from $107

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 Love Field Airport to Chicago departing on 8/5. 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
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
6:05 am - 8:15 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
10:30 am - 2:15 pm
MDW
-
DAL
3h 45m
1 stop
$199Southwest
Sat, Aug 22 - Tue, Aug 25
Southwest Logo
6:00 am - 8:10 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
12:30 pm - 4:45 pm
MDW
-
DAL
4h 15m
1 stop
$203Southwest
Wed, Aug 12 - Sat, Aug 15
Southwest Logo
6:05 am - 8:15 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
8:50 am - 2:40 pm
MDW
-
DAL
5h 50m
2 stops
$204Southwest
Sat, Aug 22 - Tue, Aug 25
Southwest Logo
8:00 am - 1:20 pm
DAL
-
MDW
5h 20m
1 stop
Southwest Logo
10:30 am - 2:15 pm
MDW
-
DAL
3h 45m
1 stop
$208Southwest
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
8:15 am - 2:10 pm
DAL
-
MDW
5h 55m
2 stops
Southwest Logo
10:05 am - 2:05 pm
MDW
-
DAL
4h 00m
1 stop
$209Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
6:00 am - 8:10 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
6:00 am - 8:10 am
MDW
-
DAL
2h 10mnonstop
$210Southwest
Tue, Aug 4 - Tue, Aug 11
Southwest Logo
5:00 pm - 7:10 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
7:00 pm - 9:15 pm
MDW
-
DAL
2h 15mnonstop
$211Southwest
Sat, Aug 15 - Mon, Aug 17
Southwest Logo
2:55 pm - 8:10 pm
DAL
-
MDW
5h 15m
1 stop
Southwest Logo
12:30 pm - 4:45 pm
MDW
-
DAL
4h 15m
1 stop
$213Southwest
Wed, Aug 12 - Sat, Aug 15
Delta Logo
6:33 pm - 11:57 pm
DAL
-
ORD
5h 24m
1 stop
Delta Logo
8:05 am - 1:52 pm
ORD
-
DAL
5h 47m
1 stop
$291Delta
Wed, Aug 12 - Wed, Aug 26
Delta Logo
2:57 pm - 8:55 pm
DAL
-
ORD
5h 58m
1 stop
Delta Logo
6:00 am - 1:52 pm
ORD
-
DAL
7h 52m
2 stops
$296Delta
Sat, Aug 22 - Sat, Aug 29

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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
Aug 12
DAL6:33 pmDallas Love Field
5h 24m
1 stop
ORD11:57 pmChicago O'Hare Intl
Aug 26
ORD8:05 amChicago O'Hare Intl
5h 47m
1 stop
DAL1:52 pmDallas Love Field
$291
Delta
Aug 22
DAL2:57 pmDallas Love Field
5h 58m
1 stop
ORD8:55 pmChicago O'Hare Intl
Aug 29
ORD6:00 amChicago O'Hare Intl
7h 52m
2 stops
DAL1:52 pmDallas Love Field
$296
Delta
Aug 12
DAL6:33 pmDallas Love Field
5h 24m
1 stop
ORD11:57 pmChicago O'Hare Intl
Aug 27
ORD5:30 amChicago O'Hare Intl
5h 54m
1 stop
DAL11:24 amDallas Love Field
$301

Southwest flights from Dallas Love Field Airport to Chicago

Our best Southwest deals on Dallas Love Field Airport to Chicago flight tickets
Southwest
Aug 22
DAL6:05 amDallas Love Field
2h 10m
MDW8:15 amChicago Midway
Aug 25
MDW10:30 amChicago Midway
3h 45m
1 stop
DAL2:15 pmDallas Love Field
$199
Southwest
Aug 12
DAL6:00 amDallas Love Field
2h 10m
MDW8:10 amChicago Midway
Aug 15
MDW12:30 pmChicago Midway
4h 15m
1 stop
DAL4:45 pmDallas Love Field
$203
Southwest
Aug 22
DAL6:05 amDallas Love Field
2h 10m
MDW8:15 amChicago Midway
Aug 25
MDW8:50 amChicago Midway
5h 50m
2 stops
DAL2:40 pmDallas Love Field
$204

momondo Fare Finder

 
Customize your flight search to find flights from Dallas Love Field Airport to Chicago 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 July 7, 2026.
Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 8/22

6:05 am-8:15 am

Nonstop2h 10m

Chicago Midway

Tue 8/25

10:30 am-2:15 pm

1 stop3h 45m

$199

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 8/12

6:00 am-8:10 am

Nonstop2h 10m

Chicago Midway

Sat 8/15

12:30 pm-4:45 pm

1 stop4h 15m

$203

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 8/22

6:05 am-8:15 am

Nonstop2h 10m

Chicago Midway

Tue 8/25

8:50 am-2:40 pm

2 stops5h 50m

$204

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 9/5

8:00 am-1:20 pm

1 stop5h 20m

Chicago Midway

Tue 9/8

10:30 am-2:15 pm

1 stop3h 45m

$208

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 9/12

8:15 am-2:10 pm

2 stops5h 55m

Chicago Midway

Sat 9/19

10:05 am-2:05 pm

1 stop4h 00m

$209
Quickest round-trip

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 8/4

6:00 am-8:10 am

Nonstop2h 10m

Chicago Midway

Tue 8/11

6:00 am-8:10 am

Nonstop2h 10m

$210

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 8/15

5:00 pm-7:10 pm

Nonstop2h 10m

Chicago Midway

Mon 8/17

7:00 pm-9:15 pm

Nonstop2h 15m

$211

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 8/12

2:55 pm-8:10 pm

1 stop5h 15m

Chicago Midway

Sat 8/15

12:30 pm-4:45 pm

1 stop4h 15m

$213

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 8/12

6:33 pm-11:57 pm

1 stop5h 24m

Chicago O'Hare Intl

Wed 8/26

8:05 am-1:52 pm

1 stop5h 47m

$291

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sat 8/22

2:57 pm-8:55 pm

1 stop5h 58m

Chicago O'Hare Intl

Sat 8/29

6:00 am-1:52 pm

2 stops7h 52m

$296

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?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Dallas Love Field Airport, with most prices found around $103. If you’re not able to fly to Chicago in November, then August is your next best option. Flight prices from Dallas Love Field Airport to Chicago during August average around $130.

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 Friday when prices can be found for as low as $271. 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 $552.

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 $243. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $484.

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?

No. A direct flight is the cheapest option for a flight between Dallas Love Field Airport to Chicago.

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

$214

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 $214. The best round-trip flight deal from Dallas Love Field Airport to Chicago found on momondo in the last 72 hours is $362.
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
7.9
4,250 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 49 Southwest flights for this route in a normal week, average airfare is usually $354 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

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport