CHI - DAL

$55 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 1/21. 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
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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Everything you should know

Cheapest round-trip
$109
Overall average: $240
Southwest
Thu 1/8Thu 1/15
MDW - DAL • Non-stop
Cheapest one-way
$55
Typical prices: $121-$362
Southwest
Wed 1/21
ORD - DAL • Non-stop
Top airlines
Southwest
Cheapest • from $109 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD-DAL
Cheapest • 6% average savings
MDW-DAL
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 49% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 31% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight 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

Thu, Jan 8 - Thu, Jan 15
Southwest Logo
8:00 pm - 10:25 pmMDW-DAL
2h 25mnonstop
Southwest Logo
12:45 pm - 2:55 pmDAL-MDW
2h 10mnonstop
$109Southwest
Find Deal
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
2:15 pm - 4:55 pmORD-DAL
2h 40mnonstop
Southwest Logo
10:35 am - 1:00 pmDAL-ORD
2h 25mnonstop
$113Southwest
Find Deal
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
12:15 pm - 2:45 pmMDW-DAL
2h 30mnonstop
Southwest Logo
6:30 pm - 8:40 pmDAL-MDW
2h 10mnonstop
$117Southwest
Find Deal
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
2:15 pm - 4:55 pmORD-DAL
2h 40mnonstop
Southwest Logo
10:35 am - 1:00 pmDAL-ORD
2h 25mnonstop
$117Southwest
Find Deal
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
1:45 pm - 9:05 pmORD-DAL
7h 20m1 stop
Southwest Logo
10:35 am - 1:00 pmDAL-ORD
2h 25mnonstop
$141Southwest
Find Deal
Thu, Jan 8 - Thu, Jan 15
Southwest Logo
10:00 am - 2:15 pmMDW-DAL
4h 15m1 stop
Southwest Logo
12:45 pm - 2:55 pmDAL-MDW
2h 10mnonstop
$143Southwest
Find Deal
Wed, Dec 10 - Sat, Dec 13
Southwest Logo
1:20 pm - 3:45 pmMDW-DAL
2h 25mnonstop
Southwest Logo
4:50 pm - 7:05 pmDAL-MDW
2h 15mnonstop
$145Southwest
Find Deal
Fri, Jan 30 - Mon, Feb 2
Southwest Logo
1:30 pm - 7:00 pmMDW-DAL
5h 30m1 stop
Southwest Logo
6:30 pm - 8:40 pmDAL-MDW
2h 10mnonstop
$146Southwest
Find Deal
Wed, Dec 17 - Wed, Dec 24
Delta Logo
5:30 am - 1:15 pmORD-DAL
7h 45m1 stop
Delta Logo
4:55 pm - 12:02 amDAL-ORD
7h 07m1 stop
$177Delta
Find Deal
Wed, Nov 12 - Wed, Nov 19
Delta Logo
12:47 pm - 5:50 pmMDW-DAL
5h 03m1 stop
Delta Logo
10:11 am - 4:39 pmDAL-MDW
6h 28m1 stop
$188Delta
Find Deal
Booking Insights

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.

How much is a round-trip flight from Chicago to Dallas Love Field Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Dallas Love Field Airport departing in January.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Dallas Love Field Airport costs $137 on the route between Chicago O'Hare Intl Airport (ORD) and Dallas Love Field Airport (DAL). Over the past month, this route was, on average, 6% cheaper than other Chicago-Dallas Love Field Airport routes. The most popular route is between Chicago Midway Airport (MDW) and Dallas Love Field Airport (DAL).

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 Saturday, with Monday 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 September, where tickets cost $179 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $389 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 $237 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 3 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonJune
Cheapest flight$55
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago O'Hare 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 $55 for a one-way ticket and $109 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 O'Hare 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.

  • Which airline alliances offer flights from Chicago to Dallas Love Field?

    oneworld is the only airline alliance operating flights between Chicago and Dallas Love Field.

  • 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 Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Dallas are Southwest and Frontier. With an average price for the route of $286 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $125 and an overall rating of 5.8.

  • 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 $150 or less one-way and $221 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 airlines flying 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 4241 reviews
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

2.0 MediocrePrincess, Oct 2025MSY - DAL
Read more Southwest reviews

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

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.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

Everything you need to know for your flight from Chicago to Love Field

Information on your arrival and departure airports

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