DAL - CHI

$74 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 4/18. 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
$147
Overall average: $339
Southwest
Sat 4/18Sat 4/18
DAL - ORD • Non-stop
Cheapest one-way
$74
Typical prices: $128-$353
Southwest
Sat 4/18
DAL - ORD • Non-stop
Top airlines
Cheapest • from $147 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 13m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 2% average savings
Most popular
Insights
Insights
Insights
Insights
When to travel
Cheapest • 45% price drop
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, Apr 18 - Sat, Apr 18
Southwest Logo
9:00 am - 11:30 am
DAL
-
ORD
2h 30mnonstop
Southwest Logo
2:05 pm - 4:45 pm
ORD
-
DAL
2h 40mnonstop
$147Southwest
Sat, Apr 18 - Sat, Apr 18
Southwest Logo
6:25 am - 8:35 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
3:05 pm - 5:30 pm
MDW
-
DAL
2h 25mnonstop
$147Southwest
Sat, Apr 18 - Sat, Apr 18
Southwest Logo
11:00 am - 2:35 pm
DAL
-
MDW
3h 35m
1 stop
Southwest Logo
6:15 pm - 8:40 pm
MDW
-
DAL
2h 25mnonstop
$153Southwest
Sat, Apr 18 - Sat, Apr 18
Southwest Logo
9:00 am - 11:30 am
DAL
-
ORD
2h 30mnonstop
Southwest Logo
1:55 pm - 8:15 pm
ORD
-
DAL
6h 20m
1 stop
$157Southwest
Sat, Apr 11 - Sat, Apr 11
Southwest Logo
6:25 am - 8:35 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
2:15 pm - 8:15 pm
MDW
-
DAL
6h 00m
1 stop
$157Southwest
Tue, Apr 21 - Sat, Apr 25
Southwest Logo
8:45 am - 11:10 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
2:05 pm - 4:45 pm
ORD
-
DAL
2h 40mnonstop
$162Southwest
Sat, Apr 18 - Wed, Apr 22
Southwest Logo
3:15 pm - 5:30 pm
DAL
-
MDW
2h 15mnonstop
Southwest Logo
5:30 am - 7:55 am
MDW
-
DAL
2h 25mnonstop
$162Southwest
Sat, Apr 18 - Sat, Apr 18
Southwest Logo
7:30 am - 1:20 pm
DAL
-
ORD
5h 50m
1 stop
Southwest Logo
3:05 pm - 9:55 pm
ORD
-
DAL
6h 50m
1 stop
$167Southwest
Sat, Apr 18 - Wed, Apr 22
Southwest Logo
11:00 am - 2:35 pm
DAL
-
MDW
3h 35m
1 stop
Southwest Logo
4:00 pm - 6:25 pm
MDW
-
DAL
2h 25mnonstop
$168Southwest
Wed, Apr 8 - Sat, Apr 11
Southwest Logo
8:45 am - 11:10 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
2:05 pm - 4:45 pm
ORD
-
DAL
2h 40mnonstop
$171Southwest
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.

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

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

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 $165 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, 2% 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 Tuesday, 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 $308 respectively.

Good to know

Low seasonJanuary
Cheapest flight$74
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 11% 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 $74 for a one-way ticket and $147 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 $258 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 $132 or less one-way and $229 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 4319 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

I elected to pay for the upgrades and found very little difference

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

I elected to pay for the upgrades and found very little difference

WiFi was not working and didn’t have a beverage service

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

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.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

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.

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.

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

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.

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

Information on your arrival and departure airports