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 2/14. 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, 0 bags

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
$157
Typical prices: $207-$380
Southwest
Tue 2/17Tue 2/24
MDW - DAL • Non-stop
Cheapest one-way
$79
Typical prices: $138-$164
Southwest
Sat 2/14
MDW - DAL • Non-stop
Top routes
ORD
-
DAL
Cheapest • 1% 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 52% 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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We hope you love your trip to Love Field!
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

Tue, Feb 17 - Tue, Feb 24
Southwest Logo
8:30 pm - 10:55 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
6:30 pm - 8:40 pm
DAL
-
MDW
2h 10mnonstop
$157Southwest
Sat, Feb 14 - Tue, Feb 17
Southwest Logo
3:05 pm - 5:40 pm
ORD
-
DAL
2h 35mnonstop
Southwest Logo
10:35 am - 1:00 pm
DAL
-
ORD
2h 25mnonstop
$157Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
8:30 pm - 10:55 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
2:25 pm - 7:55 pm
DAL
-
MDW
5h 30m
1 stop
$167Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
11:55 am - 9:00 pm
ORD
-
DAL
9h 05m
1 stop
Southwest Logo
10:35 am - 1:00 pm
DAL
-
ORD
2h 25mnonstop
$167Southwest
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
7:30 pm - 9:55 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
7:05 am - 9:15 am
DAL
-
MDW
2h 10mnonstop
$168Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
5:20 am - 7:55 am
MDW
-
DAL
2h 35mnonstop
Southwest Logo
1:45 pm - 7:05 pm
DAL
-
MDW
5h 20m
2 stops
$173Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
1:45 pm - 10:40 pm
ORD
-
DAL
8h 55m
2 stops
Southwest Logo
10:35 am - 1:00 pm
DAL
-
ORD
2h 25mnonstop
$173Southwest
Sat, Mar 7 - Mon, Mar 9
Southwest Logo
5:30 am - 8:05 am
MDW
-
DAL
2h 35mnonstop
Southwest Logo
6:35 pm - 8:45 pm
DAL
-
MDW
2h 10mnonstop
$174Southwest
Wed, Feb 11 - Wed, Feb 18
Delta Logo
6:00 am - 1:28 pm
MDW
-
DAL
7h 28m
1 stop
Delta Logo
10:45 am - 5:45 pm
DAL
-
MDW
7h 00m
1 stop
$177Delta
Wed, Mar 11 - Wed, Mar 25
Delta Logo
9:50 am - 3:13 pm
ORD
-
DAL
5h 23m
1 stop
Delta Logo
3:59 pm - 9:10 pm
DAL
-
ORD
5h 11m
1 stop
$177Delta
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 cheapest return flight from Chicago to Dallas Love Field Airport costs $186 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, 1% 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, Wednesday 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 Friday 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 November and March, where the average cost of round-trip tickets is $367 and $335 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 $270, 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, which saves you about 52% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonJune
Cheapest flight$79
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 $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, JetBlue, 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 American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Dallas are Southwest and American Airlines. With an average price for the route of $290 and an overall rating of 8.0, Southwest is the most popular choice. American Airlines is also a great choice for the route, with an average price of $347 and an overall rating of 7.2.

  • 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 $161 or less one-way and $241 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 4261 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

10.0 ExcellentManetta, Jan 2026
MDW - CLT
Read more Southwest reviews

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No delays and arrived to destination 30 min early. Staff was super friendly.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Lower WiFi prices; allow us to see our flight on a map; more variety of drink choices.

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.

Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

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

Information on your arrival and departure airports