DAL - CHI

$79 Find Cheap Flights from Dallas Love Field to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Love Field to Chicago departing on 3/7. 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 Chicago

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

Cheapest round-trip
$157
Overall average: $287
Southwest
Sat 3/7Tue 3/10
DAL - ORD • Non-stop
Cheapest non-stop
$157
Typical prices: $187-$439
Southwest
Sat 3/7Wed 3/11
DAL - ORD • Non-stop
Top airlines
Southwest
Cheapest • from $157 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
DAL
-
ORD
Cheapest • 19% average savings
DAL
-
MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 46% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Love Field to Chicago 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 Love Field to Chicago

Sat, Mar 7 - Tue, Mar 10
Southwest Logo
8:40 am - 11:05 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
4:15 pm - 6:55 pm
ORD
-
DAL
2h 40mnonstop
$157Southwest
Sat, Mar 7 - Wed, Mar 11
Southwest Logo
6:55 pm - 9:05 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
8:35 pm - 11:05 pm
MDW
-
DAL
2h 30mnonstop
$157Southwest
Sat, Feb 21 - Sat, Feb 28
Southwest Logo
10:35 am - 1:00 pm
DAL
-
ORD
2h 25mnonstop
Southwest Logo
3:05 pm - 5:40 pm
ORD
-
DAL
2h 35mnonstop
$159Southwest
Sat, Mar 7 - Tue, Mar 10
Southwest Logo
8:40 am - 11:05 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
4:50 pm - 11:05 pm
ORD
-
DAL
6h 15m
1 stop
$167Southwest
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
10:50 am - 2:55 pm
DAL
-
MDW
4h 05m
1 stop
Southwest Logo
4:25 pm - 6:55 pm
MDW
-
DAL
2h 30mnonstop
$167Southwest
Wed, Mar 4 - Wed, Mar 4
Southwest Logo
10:25 am - 12:35 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
4:25 pm - 6:55 pm
MDW
-
DAL
2h 30mnonstop
$168Southwest
Sat, Mar 7 - Tue, Mar 10
Southwest Logo
7:35 am - 2:20 pm
DAL
-
ORD
6h 45m
1 stop
Southwest Logo
4:15 pm - 6:55 pm
ORD
-
DAL
2h 40mnonstop
$169Southwest
Tue, Mar 3 - Sat, Mar 7
Southwest Logo
4:50 pm - 7:00 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
10:00 am - 3:30 pm
MDW
-
DAL
5h 30m
1 stop
$169Southwest
Sat, Mar 7 - Sat, Mar 7
Southwest Logo
8:40 am - 11:05 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
4:15 pm - 6:55 pm
ORD
-
DAL
2h 40mnonstop
$171Southwest
Sat, Mar 7 - Tue, Mar 10
Southwest Logo
8:40 am - 11:05 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
2:40 pm - 10:40 pm
ORD
-
DAL
8h 00m
2 stops
$172Southwest
Booking Insights

KAYAK's insights & trends for Love Field to Chicago flights

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

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

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

The cheapest return flight from Dallas Love Field Airport to Chicago costs $111 on the route between Dallas Love Field Airport (DAL) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 19% cheaper than other Dallas Love Field Airport-Chicago routes. The most popular route is between Dallas Love Field Airport (DAL) and Chicago Midway Airport (MDW).

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

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

Your flight ticket price will generally be cheaper if you fly to Chicago on a Saturday and more expensive on a Friday. On your return trip to Dallas Love Field, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Dallas Love Field Airport to Chicago, 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 Dallas Love Field Airport to Chicago is October, where tickets cost $128 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $323 and $287 respectively.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Dallas Love Field to Chicago O'Hare Airport

When to book flights from Love Field to Chicago

Are your dates flexible? Find out the best times to travel from Love Field to Chicago 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 Dallas Love Field to Chicago flights

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

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

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    When flying out of Dallas Love Field you will be using Dallas Love Field. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Dallas to Chicago are Southwest and Spirit Airlines. With an average price for the route of $257 and an overall rating of 8.0, Southwest is the most popular choice. Spirit Airlines is also a great choice for the route, with an average price of $125 and an overall rating of 6.3.

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

    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 Dallas Love Field to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Dallas Love Field 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 Dallas Love Field to Chicago?

    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 Chicago with an airline and back to Dallas Love Field with another airline.

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

    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 Chicago from Dallas Love Field 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 Dallas Love Field Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $133 or less one-way and $212 or less round-trip.

Prefer to fly direct from Dallas Love Field to Chicago?

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

Direct departures

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

Direct returns

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

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

 
See real verified KAYAK customer reviews for airlines flying from Dallas to Chicago. 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 Love Field to Chicago? 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 4268 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great vacation. Can't wait till next year for another one.

The seats were comfortable, and the boarding process was pretty smooth.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Honestly horrible. The plane on the way back was delayed 6 times with no explanation on why. When I asked for a refund or some money back because I had to miss a day of work because of the desk, they told me no. Because of how poorly it was handled I will most likely never take spirit again

I hope you continue to be one of the great company

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

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.

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

Information on your arrival and departure airports