CHI - DAL

$74 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 5/21. 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

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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Cheap Flights from Chicago to Love Field

 
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.

Recent round-trip flight deals from Chicago to Love Field

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Love Field.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
8:40 pm - 11:00 pmMDW-DAL
2h 20mnonstop
Southwest Logo
6:05 pm - 10:30 pmDAL-MDW
4h 25m1 stop
$173Southwest
Find Deal
Wed, May 21 - Sat, May 24
Southwest Logo
1:25 pm - 6:30 pmMDW-DAL
5h 05m1 stop
Southwest Logo
6:05 pm - 10:30 pmDAL-MDW
4h 25m1 stop
$183Southwest
Find Deal
Wed, May 21 - Sat, May 24
Southwest Logo
5:55 pm - 8:20 pmMDW-DAL
2h 25mnonstop
Southwest Logo
6:40 pm - 8:50 pmDAL-MDW
2h 10mnonstop
$188Southwest
Find Deal
Sat, May 24 - Sat, May 31
Southwest Logo
5:45 pm - 8:10 pmORD-DAL
2h 25mnonstop
Southwest Logo
7:40 pm - 10:00 pmDAL-ORD
2h 20mnonstop
$188Southwest
Find Deal
Sat, May 24 - Sat, May 31
Southwest Logo
7:30 am - 9:50 amMDW-DAL
2h 20mnonstop
Southwest Logo
7:50 am - 10:05 amDAL-MDW
2h 15mnonstop
$189Southwest
Find Deal
Sun, May 25 - Sun, Jun 1
Southwest Logo
7:30 am - 10:00 amORD-DAL
2h 30mnonstop
Southwest Logo
8:20 am - 10:45 amDAL-ORD
2h 25mnonstop
$189Southwest
Find Deal
Sun, May 25 - Sun, Jun 1
Southwest Logo
7:30 am - 10:00 amORD-DAL
2h 30mnonstop
Southwest Logo
7:40 pm - 10:00 pmDAL-ORD
2h 20mnonstop
$192Southwest
Find Deal
Wed, May 21 - Sat, May 24
Southwest Logo
5:40 pm - 9:40 pmMDW-DAL
4h 00m1 stop
Southwest Logo
6:45 pm - 11:10 pmDAL-MDW
4h 25m1 stop
$193Southwest
Find Deal
Tue, May 20 - Tue, May 27
Delta Logo
6:00 am - 10:56 amMDW-DAL
4h 56m1 stop
Delta Logo
3:59 pm - 9:27 pmDAL-MDW
5h 28m1 stop
$208Delta
Find Deal
Sun, May 25 - Tue, Jun 3
Delta Logo
10:25 am - 5:44 pmMDW-DAL
7h 19m1 stop
Delta Logo
3:59 pm - 9:27 pmDAL-MDW
5h 28m1 stop
$209Delta
Find Deal
Sat, May 24 - Wed, May 28
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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 $147 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 $147.

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 Tuesday, 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 October, where tickets cost $215 (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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $157 on average.

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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonJune
High seasonFebruary
Cheapest flight$74
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 3% 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 $74 for a one-way ticket and $173 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?

    Only American Airlines offers 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.

  • Which is the best airline for flights from Chicago to Dallas, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Dallas are Southwest and Delta. With an average price for the route of $286 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $329 and an overall rating of 8.0.

  • 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 $109 or less one-way and $190 or less round-trip.

Prefer to fly 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
See more direct flights

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 4294 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.1Food
Airline reviews

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.

10.0 ExcellentReginald, Mar 2025MDW - LGA
Read more Southwest reviews

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.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

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