CHI - DAL

$79 Find Cheap Flights from Chicago to Dallas Love Field

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Love Field departing on 8/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Dallas Love Field Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Dallas, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Dallas, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Chicago to Love Field (CHI-DAL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Love Field that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Love Field

Wed, Aug 6 - Wed, Aug 13
Southwest Logo
12:50 pm - 3:05 pmMDW-DAL
2h 15mnonstop
Southwest Logo
7:20 pm - 9:30 pmDAL-MDW
2h 10mnonstop
$157Southwest
Find Deal
Wed, Aug 6 - Wed, Aug 13
Southwest Logo
7:30 am - 9:55 amORD-DAL
2h 25mnonstop
Southwest Logo
8:20 am - 10:45 amDAL-ORD
2h 25mnonstop
$157Southwest
Find Deal
Wed, Aug 6 - Wed, Aug 13
Southwest Logo
12:50 pm - 3:05 pmMDW-DAL
2h 15mnonstop
Southwest Logo
7:35 am - 12:10 pmDAL-MDW
4h 35m1 stop
$167Southwest
Find Deal
Wed, Aug 6 - Wed, Aug 13
Southwest Logo
7:30 am - 9:55 amORD-DAL
2h 25mnonstop
Southwest Logo
9:20 am - 3:20 pmDAL-ORD
6h 00m1 stop
$167Southwest
Find Deal
Wed, Aug 6 - Sat, Aug 16
Southwest Logo
1:30 pm - 3:50 pmORD-DAL
2h 20mnonstop
Southwest Logo
7:45 am - 4:25 pmDAL-ORD
8h 40m2 stops
$172Southwest
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Sat, Sep 6 - Sat, Sep 13
Southwest Logo
1:20 pm - 6:55 pmMDW-DAL
5h 35m1 stop
Southwest Logo
12:30 pm - 7:05 pmDAL-MDW
6h 35m1 stop
$177Southwest
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Thu, Aug 14 - Sun, Aug 17
Southwest Logo
7:30 am - 9:55 amORD-DAL
2h 25mnonstop
Southwest Logo
7:05 pm - 9:30 pmDAL-ORD
2h 25mnonstop
$177Southwest
Find Deal
Thu, Aug 7 - Sun, Aug 10
Southwest Logo
8:55 pm - 11:10 pmMDW-DAL
2h 15mnonstop
Southwest Logo
7:55 am - 10:10 amDAL-MDW
2h 15mnonstop
$178Southwest
Find Deal
Sat, Aug 16 - Wed, Aug 20
Delta Logo
10:31 am - 3:07 pmMDW-DAL
4h 36m1 stop
Delta Logo
5:45 am - 11:48 amDAL-MDW
6h 03m1 stop
$197Delta
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Sat, Aug 16 - Wed, Aug 20
Delta Logo
5:45 am - 10:53 amORD-DAL
5h 08m1 stop
Delta Logo
3:52 pm - 9:36 pmDAL-ORD
5h 44m1 stop
$197Delta
Find Deal
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KAYAK's insights & trends for Chicago to Love Field flights

Get data-powered insights and trends into flights from Chicago to Love Field to help you find the cheapest flights, the best time to fly and much more.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Dallas Love Field Airport.

Our data shows that the cheapest route for a return flight from Chicago to Dallas Love Field Airport cost $157 and was between Chicago Midway Airport (MDW) and Dallas Love Field Airport (DAL). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $157.

What’s the cheapest day of the week to fly from Chicago to Dallas Love Field?

The average price of all round-trip flights from Chicago to Dallas Love Field Airport clicked on KAYAK for each day over the last 12 months.

For Chicago to Dallas Love Field, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Dallas Love Field back to Chicago, the best deals are generally found on Wednesday, with Sunday being the most expensive.

What is the cheapest month to fly from Chicago to Dallas Love Field Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Dallas Love Field Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Dallas Love Field Airport is April, where tickets cost $199 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $393 and $368 respectively.

Can I save money by flying with a layover from Chicago to Dallas Love Field Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $199, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago to Dallas Love Field Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Dallas Love Field Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Dallas Love Field Airport, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonJune
High seasonMay
Cheapest flight$79
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Chicago Midway Airport to Dallas Love Field

When to book flights from Chicago to Love Field

Are your dates flexible? Find out the best times to travel from Chicago to Love Field based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Dallas Love Field flights

  • What is the cheapest flight from Chicago to Dallas Love Field Airport?

    In the last 3 days, the lowest price for a flight from Chicago to Dallas Love Field Airport was $79 for a one-way ticket and $157 for a round-trip.

  • Do I need a passport to fly between Chicago and Dallas Love Field?

    No

  • Which airports will I be using when flying from Chicago to Dallas Love Field?

    There are 2 airports in Chicago (Chicago Midway and Chicago O'Hare Intl.) and only 1 airport in Dallas Love Field (Dallas Love Field). The cheapest flights are generally found on the Chicago Midway Airport to Dallas Love Field flight route.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Dallas Love Field?

    American Airlines, and Delta offer inflight Wi-Fi service on the Chicago to Dallas Love Field flight route.

  • Which aircraft models fly most regularly from Chicago to Dallas Love Field?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago to Dallas Love Field flight route.

  • On which days can I fly direct from Chicago to Dallas Love Field?

    There are nonstop flights from Chicago to Dallas Love Field on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago to Dallas Love Field?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Dallas Love Field.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Dallas Love Field?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Dallas Love Field from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Dallas Love Field?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Dallas Love Field with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Dallas Love Field?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Dallas Love Field from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Dallas Love Field Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $133 or less one-way and $192 or less round-trip.

Prefer to fly direct from Chicago to Dallas Love Field?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Dallas Love Field.
Find which airlines fly direct from Chicago to Dallas Love Field Airport, which days they fly and book direct flights.

Direct departures

Chicago to Dallas Love Field

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Dallas Love Field to Chicago

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 3 airlines serving from Chicago to Love Field

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Dallas. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Love Field? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4243 reviews
8.1Boarding
8.6Crew
7.0Food
7.6Entertainment
8.0Comfort
Airline reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

Easy to book and to get check in and get on and off.

Excellent experience. WiFi worked on this leg of My trip

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

Pretty bad gate mgmt upon arrival. No open gates and we had to wait at midnight. Shouldn’t be a surprise that an aircraft is coming in.

Comfortable plane ride however on delays disappointment no real details as to why the delays when other flights are leaving the airport

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

It’s a great flight. Service is good. Staff is awesome.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

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