CHI - DAL

$72 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 9/23. 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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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

Tue, Sep 30 - Wed, Oct 1
Southwest Logo
3:35 pm - 5:50 pmMDW-DAL
2h 15mnonstop
Southwest Logo
8:10 am - 10:25 amDAL-MDW
2h 15mnonstop
$143Southwest
Find Deal
Tue, Sep 30 - Wed, Oct 1
Southwest Logo
7:30 am - 9:55 amORD-DAL
2h 25mnonstop
Southwest Logo
8:20 am - 10:45 amDAL-ORD
2h 25mnonstop
$143Southwest
Find Deal
Wed, Oct 15 - Sat, Oct 18
Southwest Logo
12:45 pm - 3:00 pmMDW-DAL
2h 15mnonstop
Southwest Logo
2:15 pm - 4:30 pmDAL-MDW
2h 15mnonstop
$147Southwest
Find Deal
Wed, Nov 5 - Sat, Nov 8
Southwest Logo
2:15 pm - 4:50 pmORD-DAL
2h 35mnonstop
Southwest Logo
10:35 am - 1:00 pmDAL-ORD
2h 25mnonstop
$147Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
8:25 pm - 10:40 pmMDW-DAL
2h 15mnonstop
Southwest Logo
6:25 am - 8:35 amDAL-MDW
2h 10mnonstop
$151Southwest
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
7:30 am - 10:00 amORD-DAL
2h 30mnonstop
Southwest Logo
12:50 pm - 3:20 pmDAL-ORD
2h 30mnonstop
$151Southwest
Find Deal
Tue, Oct 14 - Wed, Oct 15
Southwest Logo
6:55 pm - 9:15 pmMDW-DAL
2h 20mnonstop
Southwest Logo
6:00 am - 9:55 amDAL-MDW
3h 55m1 stop
$153Southwest
Find Deal
Wed, Nov 5 - Wed, Nov 12
Southwest Logo
1:45 pm - 9:05 pmORD-DAL
7h 20m1 stop
Southwest Logo
10:35 am - 1:00 pmDAL-ORD
2h 25mnonstop
$153Southwest
Find Deal
Wed, Feb 11 - Wed, Feb 18
Delta Logo
10:35 am - 5:55 pmMDW-DAL
7h 20m1 stop
Delta Logo
10:20 am - 4:25 pmDAL-MDW
6h 05m1 stop
$197Delta
Find Deal
Sat, Nov 8 - Mon, Nov 10
Delta Logo
6:10 pm - 11:55 pmORD-DAL
5h 45m1 stop
Delta Logo
3:59 pm - 12:01 amDAL-ORD
8h 02m1 stop
$197Delta
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.

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 absolute cheapest return flight from Chicago to Dallas Love Field Airport costs $147 on the route between Chicago O'Hare Intl Airport (ORD) and Dallas Love Field Airport (DAL). However, over the past month, flights between Chicago Midway Airport (MDW) and Dallas Love Field Airport (DAL) were, on average, 1% cheaper than other Chicago-Dallas Love Field Airport routes. The most popular route is between Chicago O'Hare Intl Airport (ORD) 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 Wednesday, 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 $197 (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 $228, 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 4 weeks before departure, which saves you about 64% 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$72
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 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 $72 for a one-way ticket and $143 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.

  • 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 $281 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 $121 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 $118 or less one-way and $187 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 4238 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

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

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

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.

Excellent experience. WiFi worked on this leg of My trip

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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