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DAL - CHI

$117 Find Cheap Flights from Dallas Love Field to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$233
Typical prices: $253-$440
Southwest
Sat 10/27Sat 11/3
DAL - MDW • Non-stop
Cheapest one-way
$117
Typical prices: $164-$289
Southwest
Sat 10/27
DAL - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 14m
Direct flights
+1
Direct flights
+1
Top routes
DAL - ORD
Cheapest • 12% average savings
DAL - MDW
Most popular
Insights
Insights
When to book
15 weeks
in advance
Our data shows that travelers who book at least 15 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 42% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Lambert-St Louis (STL)
Cheapest • Avg $176 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 5h 58m (one-way)
Insights
Insights
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We hope you love your trip to Chicago!

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

 

Cheap flights from Love Field to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Tue, Oct 27 - Tue, Oct 27
Southwest Logo
7:15 am - 9:30 amDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
9:20 pm - 11:30 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 10mnonstop
$233Southwest
Wed, Nov 4 - Wed, Nov 11
Southwest Logo
8:25 pm - 10:40 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$233Southwest
Wed, Dec 23 - Wed, Dec 30
Southwest Logo
6:05 am - 8:15 amDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
9:05 pm - 11:30 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
$233Southwest
Wed, Oct 28 - Sat, Oct 31
Southwest Logo
8:05 pm - 10:20 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
6:00 am - 8:15 amMDW  Chicago Midway-DAL Dallas Love Field
2h 15mnonstop
$233Southwest
Wed, Nov 4 - Tue, Nov 10
Southwest Logo
8:25 pm - 10:40 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
7:05 am - 9:35 amMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$233Southwest
Sat, Oct 31 - Tue, Nov 3
Southwest Logo
6:15 am - 8:25 amDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
8:45 pm - 11:10 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
$233Southwest
Wed, Nov 4 - Tue, Nov 10
Southwest Logo
8:40 am - 10:55 amDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
3:10 pm - 5:35 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
$233Southwest
Sat, Oct 31 - Tue, Nov 17
Southwest Logo
2:35 pm - 4:45 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$233Southwest
Wed, Dec 9 - Tue, Dec 15
Delta Logo
6:06 am - 12:04 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:12 pm - 10:43 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 31m1 stop Atlanta Hartsfield-Jackson
$253Delta
Tue, Dec 8 - Wed, Dec 9
Delta Logo
11:00 am - 4:16 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 16m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:02 pm - 6:09 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 07m1 stop Atlanta Hartsfield-Jackson
$253Delta

Price, demand and travel trends for Dallas Love Field Airport to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Dallas Love Field Airport to Chicago typically range from $253 to $440. The lowest price found in the past 5 days was $233, on Southwest.

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

Dallas Love Field Airport (DAL) to Chicago O'Hare Intl Airport (ORD) is the cheapest Dallas Love Field Airport to Chicago route, averaging $272 round-trip. Other Dallas Love Field Airport to Chicago routes average $349, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Dallas Love Field Airport to Chicago. It’s 15% cheaper than the average day, while Sunday is the most expensive, with prices 26% higher.

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

•January is the cheapest month to fly from Dallas Love Field Airport to Chicago at $198 round-trip.
•July ($396) and August ($392) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 100% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Dallas Love Field Airport to Chicago the cheapest?

Flights from Dallas Love Field Airport to Chicago are cheapest 15 weeks before departure. Booking in this window typically costs about 50% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Dallas Love Field Airport to Chicago flights

Low season

December

Cheapest flight

$117
Beat the crowds with an average 28% drop in travelers.
The most popular month to fly with an average 57% increase in travelers.
One-way flight from Dallas Love Field Airport to Chicago Midway 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

Your Dallas Love Field Airport to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Dallas Love Field Airport to Chicago?

    These are the earliest and latest flight times available from Dallas Love Field Airport to Chicago:

    • Earliest: departs at 6:00 am and lands at 8:14 am
    • Latest: departs at 10:55 pm and lands at 1:09 am.

    The flight takes about 2h 14m.

  • What cabin classes can I book on flights from Dallas Love Field Airport to Chicago?

    Only Economy Class is available on flights from Dallas Love Field Airport to Chicago.

  • How long is a flight from Dallas Love Field Airport to Chicago?

    A nonstop flight from Dallas Love Field Airport to Chicago takes 2h 14m, covering 802 miles.

  • Do I need a passport to fly from Dallas Love Field Airport to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Dallas Love Field Airport to Chicago flight?

    Round-trip flights from Dallas Love Field Airport to Chicago range from $253 to $440, with an average of $340 over the past 12 months. Anything below $253 counts as a good deal.

  • How expensive are last-minute Dallas Love Field Airport to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 37% above the $340 route average. Book 15 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Dallas Love Field Airport to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $176 round-trip via Lambert-St Louis (STL), compared to $342 for nonstop.

  • What is the standard checked-bag allowance on flights from Dallas Love Field Airport to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Dallas Love Field Airport to Chicago spread across the day?

    Morning is the busiest departure period on Dallas Love Field Airport to Chicago flights, with 34% of flights leaving in that window. Afternoon departures account for 34%, evening flights for 16%, and night flights for 16%.

  • Have flight prices from Dallas Love Field Airport to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $233 to $1,380. That means the highest observed fare was about 6x higher than the lowest one.

  • Which airlines offer Wi-Fi on Dallas Love Field Airport to Chicago flights?

    JetBlue is the only airline on the Dallas Love Field Airport to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Dallas Love Field Airport to Chicago looking right now?

    One-way fares from Dallas Love Field Airport to Chicago are currently lower than usual. Average one-way flight prices are about $119, which is 46% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Dallas Love Field Airport to Chicago?

    Flights from Dallas Love Field Airport to Chicago usually depart from Dallas Love Field (DAL) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Dallas Love Field Airport to Chicago pass through?

    One-stop flights from Dallas Love Field Airport to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 60% of one-stop connections
    • Orlando (MCO) - 20% of one-stop connections
    • Lambert-St Louis (STL) - 20% of one-stop connections

  • Can I save money by using flexible dates for flights from Dallas Love Field Airport to Chicago?

    Yes. Flexible dates can save you up to 32% on flights from Dallas Love Field Airport to Chicago. Saturday is the cheapest departure day at $292 round-trip on average, while Sunday is the most expensive at $429, a difference of $137.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Dallas Love Field Airport to Chicago?

    Only Southwest operates flights between Dallas Love Field Airport and Chicago.

  • How much time can I save by choosing a different layover airport from Dallas Love Field Airport to Chicago?

    Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 3h 40m, compared with 5h 58m via Atlanta Hartsfield-Jackson (ATL) and 7h 26m via Orlando (MCO).

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Dallas Love Field Airport to Chicago flights?

    Among airlines operating Dallas Love Field Airport to Chicago flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Dallas Love Field Airport to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Dallas Love Field Airport to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $292, about $137 less than Sunday fares (32% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 15 weeks before you fly. On this route, that window historically saves about 50% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Dallas Love Field Airport to Chicago trip for January. Fares historically average $198 round-trip in that month - typically $198 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Lambert-St Louis Airport (STL) can be cheaper than flying direct. The cheapest layover option averages $176 round-trip on this route - about $166 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

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

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Tuesday

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Southwest

Wednesday

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Thursday

Southwest

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Friday

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Saturday

Southwest

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Sunday

Southwest

Southwest

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Direct returns

Chicago to Dallas Love Field

Monday

Southwest

Southwest

Tuesday

Southwest

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Wednesday

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Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

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Sunday

Southwest

Southwest

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More options for your flight from Love Field to Chicago

Complete your trip to Chicago with a hotel stay or car rental

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