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 10/11. 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

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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Flights 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, Sep 24 - Tue, Sep 30
Southwest Logo
7:05 pm - 9:30 pmDAL-ORD
2h 25mnonstop
Southwest Logo
7:30 am - 9:55 amORD-DAL
2h 25mnonstop
$157Southwest
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Thu, Aug 14 - Mon, Aug 18
Southwest Logo
9:40 pm - 11:50 pmDAL-MDW
2h 10mnonstop
Southwest Logo
9:15 am - 11:30 amMDW-DAL
2h 15mnonstop
$157Southwest
Find Deal
Wed, Sep 24 - Tue, Sep 30
Southwest Logo
7:05 pm - 9:30 pmDAL-ORD
2h 25mnonstop
Southwest Logo
3:10 pm - 10:40 pmORD-DAL
7h 30m1 stop
$167Southwest
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Thu, Aug 14 - Mon, Aug 18
Southwest Logo
7:00 pm - 12:05 amDAL-MDW
5h 05m1 stop
Southwest Logo
6:50 pm - 9:05 pmMDW-DAL
2h 15mnonstop
$167Southwest
Find Deal
Wed, Sep 24 - Tue, Sep 30
Southwest Logo
8:20 am - 10:45 amDAL-ORD
2h 25mnonstop
Southwest Logo
3:10 pm - 10:05 pmORD-DAL
6h 55m2 stops
$172Southwest
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Mon, Sep 8 - Thu, Sep 11
Southwest Logo
3:20 pm - 8:25 pmDAL-MDW
5h 05m2 stops
Southwest Logo
8:55 pm - 11:10 pmMDW-DAL
2h 15mnonstop
$172Southwest
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Sat, Jul 19 - Sat, Jul 26
Southwest Logo
7:40 pm - 10:00 pmDAL-ORD
2h 20mnonstop
Southwest Logo
5:25 pm - 7:50 pmORD-DAL
2h 25mnonstop
$177Southwest
Find Deal
Sat, Jul 19 - Sat, Jul 26
Southwest Logo
9:10 pm - 11:20 pmDAL-MDW
2h 10mnonstop
Southwest Logo
5:50 am - 8:05 amMDW-DAL
2h 15mnonstop
$177Southwest
Find Deal
Wed, Aug 13 - Tue, Aug 19
Delta Logo
8:30 am - 2:19 pmDAL-ORD
5h 49m1 stop
Delta Logo
6:00 pm - 11:49 pmORD-DAL
5h 49m1 stop
$197Delta
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Mon, Aug 11 - Tue, Aug 19
Delta Logo
3:52 pm - 9:49 pmDAL-MDW
5h 57m1 stop
Delta Logo
10:11 am - 3:07 pmMDW-DAL
4h 56m1 stop
$197Delta
Find Deal
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Dallas Love Field Airport to Chicago.

Our data shows that the cheapest route for a return flight from Dallas Love Field Airport to Chicago cost $155 and was between Dallas Love Field Airport (DAL) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly from Dallas Love Field Airport (DAL) to Chicago O'Hare Intl Airport (ORD). The average price for a return flight for this route is $155.

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 Sunday. 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 July, where tickets cost $128 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is $358 and $337 respectively.

Good to know

Low seasonMarch
High seasonOctober
Cheapest flight$79
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 33% 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, 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.

  • 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 $153 or less one-way and $195 or less round-trip.

Prefer to fly 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
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
SouthwestOverall score based on 4287 reviews
7.6Entertainment
8.0Comfort
7.1Food
8.2Boarding
8.6Crew
Airline reviews

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

6.0 GoodAnonymous, May 2025HOU - MCI
Read more Southwest reviews

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The last 30 min or so, they put the heat on full. We thought we were being basted.

I like that it was on time and the staff was friendly.

No space for our carryon and needed to check at plane before boarding !

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

I will never fly with Spirit again. I was late getting through TSA after dealing with traffic and getting on the wrong shuttle. I got to the gate 2 minutes before the ticket said the gate closes and they agents were gone and doors were closed. They rescheduled my flight for 12 hours later and the agent had the nerve to tell me, “Be on time next time”. I was already upset from nothing going right for me that morning. I booked another flight through Alaska Airlines and they were very accommodating, nerer again Spirit Airlines!!!!

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

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