DAL - CHI

$123 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 5/30. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$245
Typical prices: $317-$253
Southwest
Wed 5/27Wed 6/3
DAL - ORD • Non-stop
Cheapest one-way
$123
Typical prices: $98-$139
Southwest
Sat 5/30
DAL - ORD • Non-stop
Top airlines
Cheapest • from $245 (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 15m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 11% average savings
Most popular
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% 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

Wed, May 27 - Wed, Jun 3
Southwest Logo
8:45 am - 11:10 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
11:55 am - 2:25 pm
ORD
-
DAL
2h 30mnonstop
$245Southwest
Thu, Jun 11 - Sun, Jun 14
Southwest Logo
10:50 pm - 1:00 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
5:00 am - 7:15 am
MDW
-
DAL
2h 15mnonstop
$245Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
8:45 am - 11:10 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
11:55 am - 2:25 pm
ORD
-
DAL
2h 30mnonstop
$250Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
1:10 pm - 3:25 pm
DAL
-
MDW
2h 15mnonstop
Southwest Logo
8:55 pm - 11:10 pm
MDW
-
DAL
2h 15mnonstop
$250Southwest
Wed, May 20 - Tue, Jun 2
Southwest Logo
8:45 am - 11:10 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
11:55 am - 2:25 pm
ORD
-
DAL
2h 30mnonstop
$251Southwest
Wed, May 20 - Sun, May 24
Southwest Logo
6:15 am - 8:25 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
7:20 am - 9:45 am
MDW
-
DAL
2h 25mnonstop
$251Southwest
Sat, May 30 - Mon, Jun 1
Southwest Logo
9:00 am - 11:30 am
DAL
-
ORD
2h 30mnonstop
Southwest Logo
3:45 pm - 10:55 pm
ORD
-
DAL
7h 10m
1 stop
$255Southwest
Tue, Jun 9 - Wed, Jun 17
Southwest Logo
12:00 pm - 3:55 pm
DAL
-
MDW
3h 55m
1 stop
Southwest Logo
8:55 pm - 11:10 pm
MDW
-
DAL
2h 15mnonstop
$255Southwest
Sat, May 30 - Sun, May 31
Southwest Logo
12:40 pm - 4:50 pm
DAL
-
MDW
4h 10m
1 stop
Southwest Logo
5:00 am - 7:25 am
MDW
-
DAL
2h 25mnonstop
$256Southwest
Sat, May 30 - Fri, Jun 5
Delta Logo
6:44 pm - 12:03 am
DAL
-
ORD
5h 19m
1 stop
Delta Logo
6:06 pm - 11:56 pm
ORD
-
DAL
5h 50m
1 stop
$265Delta
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 May.

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 $191 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, 11% 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 Wednesday and more expensive on a Monday. On your return trip to Dallas Love Field, you should consider flying back on a Thursday, 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 November, where tickets cost $103 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $178 and $177 respectively.

Can I save money by flying with a layover from Dallas Love Field Airport to Chicago?

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 $351, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
Cheapest flight$123
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 2% increase in price.
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 $123 for a one-way ticket and $245 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 Frontier?

    The two airlines most popular with KAYAK users for flights from Dallas to Chicago are Southwest and Frontier. With an average price for the route of $279 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 $216 and an overall rating of 5.6.

  • 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 $167 or less one-way and $286 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 airlines flying 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 4314 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

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

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

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

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

Information on your arrival and departure airports