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DAL - CHI

Find cheap flights from Dallas Love Field to Chicago from $98

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 7/9. 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
0 bags
Sat 6/8
Sat 6/15

Search 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
In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
4:38 pm - 9:38 pmDAL-ORD
5h 00m1 stop
5:59 pm - 11:56 pmORD-DAL
5h 57m1 stop
$196Delta
Find Deal
Tue, Jun 18 - Sat, Jun 29
10:25 am - 5:59 pmDAL-MDW
7h 34m1 stop
6:49 pm - 11:56 pmMDW-DAL
5h 07m1 stop
$196Delta
Find Deal
Tue, Jul 23 - Tue, Jul 30
4:24 pm - 9:41 pmDAL-ORD
5h 17m1 stop
7:00 am - 2:00 pmORD-DAL
7h 00m1 stop
$216Delta
Find Deal
Tue, Jul 23 - Thu, Aug 1
6:00 am - 11:52 amDAL-MDW
5h 52m1 stop
6:00 am - 1:47 pmMDW-DAL
7h 47m1 stop
$216Delta
Find Deal
Sun, Jun 2 - Sat, Jun 15
6:35 pm - 8:55 pmDAL-ORD
2h 20mnonstop
7:00 am - 9:25 amORD-DAL
2h 25mnonstop
$257Southwest
Find Deal
Tue, May 21 - Thu, May 23
11:20 am - 5:55 pmDAL-ORD
6h 35m1 stop
7:00 am - 9:25 amORD-DAL
2h 25mnonstop
$267Southwest
Find Deal
Tue, May 21 - Thu, May 23
2:10 pm - 10:35 pmDAL-ORD
8h 25m2 stops
1:45 pm - 4:10 pmORD-DAL
2h 25mnonstop
$272Southwest
Find Deal
Tue, May 21 - Thu, May 23
2:34 pm - 5:40 amDAL-ORD
15h 06m1 stop
9:20 pm - 1:34 pmORD-DAL
16h 14m1 stop
$424Alaska Airlines
Find Deal
Wed, May 29 - Wed, Jun 5
2:30 pm - 4:58 pmDAL-ORD
26h 28m1 stop
6:20 am - 1:30 pmORD-DAL
31h 10m1 stop
$500Alaska Airlines
Find Deal
Wed, Oct 30 - Tue, Nov 5
2:34 pm - 5:40 amDAL-ORD
15h 06m1 stop
7:29 pm - 1:34 pmORD-DAL
18h 05m1 stop
$504Alaska Airlines
Find Deal
Wed, May 29 - Sat, Jun 1

Flights from Love Field to Chicago - Travel Insights & Trends

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Dallas Love Field Airport to Chicago.
Our data shows that the cheapest route for a one-way flight from Dallas Love Field Airport to Chicago cost $142 and was between Dallas Love Field Airport and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $439.

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

The average price of all flights from Dallas Love Field Airport to Chicago clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Dallas Love Field to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Tuesdays for the best 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 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 January, where tickets cost $129 on average. On the other hand, the most expensive months are July and June, where the average cost of tickets is $271 and $228 respectively.

How far in advance should I book a flight from Dallas Love Field Airport to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Dallas Love Field Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Dallas Love Field Airport to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 62 days before departure.

Which airlines provide the cheapest flights from Dallas Love Field to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Dallas Love Field to Chicago found on KAYAK was with Delta for $98. Delta proposed a round-trip connection from $196 and Southwest from $257.

How many flights are there between Dallas Love Field Airport and Chicago per day?

Each day, there are between 13 and 22 nonstop flights that take off from Dallas Love Field Airport and land in Chicago, with an average flight time of 2h 16m. The most common departure time is 6:00 am and most flights take off in the morning, while the most flights land at Chicago Midway Airport. Each week, there are 138 flights. The most frequent day of departure is Thursday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Dallas Love Field Airport and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Dallas Love Field to Chicago take?

The duration of a nonstop flight to Chicago from Dallas Love Field is typically 2h 20m. The journey crosses a distance of 802 miles.

What’s the earliest departure time from Dallas Love Field to Chicago?

Early birds can take the earliest flight from Dallas Love Field Airport at 6:00 am and will be landing in Chicago at 8:15 am.

What’s the latest departure time from Dallas Love Field to Chicago?

If you prefer to fly at night, the latest flight from Dallas Love Field Airport to Chicago jets off at 10:20 pm and lands at 12:30 am.

Good to know

Low season

November

High season

June

Cheapest flight

$98
Best time to beat the crowds with an average 86% drop in price.
Most popular time to fly with an average 66% 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 $98 for a one-way ticket and $196 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?

    Only American Airlines offers 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.

  • 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.

See more FAQs

Prefer to fly non-stop from Dallas Love Field to Chicago?

Find which airlines fly direct from Love Field to Chicago, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

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
DeltaOverall score based on 10778 reviews
8.2Boarding
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

I love the free wifi and headrest screens. I would consider Delta even more because of this but the seats aren't so great. The snacks aren't very good in my opinion. I bought a Bloody Mary and that was great! So just be comfortable with better snacks and the airline world will be yours.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

I paid for extra leg room. The flimsy plastic seat underneath the floatation seat did not line up with the arm rests. It seemed as if the plastic part was zip tied on but immovable. This caused severe uncomfortable for the duration of the flight.

Plane was clean but they do not allow bag drop until 1 hour before flight. Just encouraging late fees and other issues. The worst I have experienced. Total hostage situation, pay or you miss your flight.

Everything was good, and most importantly on time. They have been extremely tardy in some of my flights

Book cheap flights from Dallas to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Dallas to Chicago found on KAYAK in the last 72 hours.
7/9Tue
1 stopDelta
7h 35mDAL-ORD
$98
8/13Tue
1 stopDelta
7h 39mDAL-MDW
$104
6/29Sat
1 stopDelta
5h 18mDAL-ORD
$114
5/20Mon
nonstopSouthwest
2h 25mDAL-ORD
$143
5/20Mon
nonstopSouthwest
2h 10mDAL-MDW
$143
5/14Tue
1 stopDelta
5h 35mDAL-ORD
$150
5/20Mon
1 stopSouthwest
5h 20mDAL-ORD
$152
6/4Tue
1 stopAlaska Airlines
9h 15mDAL-ORD
$217
6/12Wed
1 stopAlaska Airlines
15h 06mDAL-ORD
$220
5/29Wed
1 stopAlaska Airlines
15h 06mDAL-ORD
$268

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Last minute flights from Love Field to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Dallas to Chicago that are departing in the next 10 days.
5/11Sat
multi-stopDelta
6h 51mDAL-ORD
5/18Sat
multi-stopDelta
5h 39mORD-DAL
$279
5/14Tue
multi-stopDelta
5h 35mDAL-ORD
5/15Wed
multi-stopDelta
5h 45mORD-DAL
$303
5/14Tue
multi-stopDelta
6h 10mDAL-MDW
5/15Wed
multi-stopDelta
4h 52mMDW-DAL
$336
5/13Mon
nonstopSouthwest
2h 25mDAL-ORD
5/16Thu
nonstopSouthwest
2h 25mORD-DAL
$339
5/13Mon
nonstopSouthwest
2h 25mDAL-ORD
5/16Thu
multi-stopSouthwest
7h 00mORD-DAL
$348
5/13Mon
nonstopSouthwest
2h 10mDAL-MDW
5/14Tue
nonstopSouthwest
2h 20mMDW-DAL
$350
5/14Tue
multi-stopDelta
5h 35mDAL-ORD
5/15Wed
multi-stopDelta
5h 40mORD-DAL
$409
5/11Sat
multi-stopAlaska Airlines
15h 06mDAL-ORD
5/14Tue
multi-stopAlaska Airlines
19h 48mORD-DAL
$1,013
5/13Mon
multi-stopAlaska Airlines
9h 19mDAL-ORD
5/20Mon
multi-stopAlaska Airlines
16h 14mORD-DAL
$1,033
5/11Sat
multi-stopAlaska Airlines
21h 31mDAL-ORD
5/22Wed
multi-stopAlaska Airlines
28h 54mORD-DAL
$1,034

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Dallas Love Field - Chicago Flights

Departure:

Dallas Love Field (undefined)United States

Return flight deals:

Chicago - Dallas Love Field

Cabin classes:

$439