DAL - CHI

$149 Find Cheap Flights from Dallas Love Field to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$297
Typical prices: $230-$414
Southwest
Fri 11/9Sun 11/18
DAL - MDW • Non-stop
Cheapest one-way
$149
Typical prices: $153-$290
Southwest
Sun 10/7
DAL - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 13m
Direct flights
+1
Direct flights
+1
Top routes
DAL - ORD
Cheapest • 13% average savings
DAL - MDW
Most popular
Insights
Insights
When to book
9 weeks
in advance
Our data shows that travelers who book at least 9 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 38% 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)
Fort Leonard Wood Waynesville Regional (TBN)
Shortest trip • 4h 02m (one-way)
Insights
Insights
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Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Love Field to Chicago

Mon, Nov 9 - Wed, Nov 18
Southwest Logo
10:55 pm - 1:05 amDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
8:50 am - 11:20 amMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$297Southwest
Thu, Sep 17 - Mon, Sep 21
Southwest Logo
9:10 pm - 11:25 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
5:30 am - 7:40 amMDW  Chicago Midway-DAL Dallas Love Field
2h 10mnonstop
$297Southwest
Tue, Sep 22 - Mon, Sep 28
Southwest Logo
7:35 am - 9:50 amDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:40 pm - 10:55 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 15mnonstop
$297Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
6:30 pm - 8:40 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
5:30 am - 7:40 amMDW  Chicago Midway-DAL Dallas Love Field
2h 10mnonstop
$297Southwest
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
9:10 pm - 11:25 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:40 pm - 10:55 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 15mnonstop
$297Southwest
Sat, Sep 26 - Mon, Sep 28
Southwest Logo
5:00 pm - 7:15 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
5:55 pm - 8:10 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 15mnonstop
$297Southwest
Mon, Oct 12 - Sat, Oct 17
Southwest Logo
10:55 pm - 1:05 amDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
10:40 am - 12:55 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 15mnonstop
$297Southwest
Thu, Oct 1 - Sat, Oct 17
Southwest Logo
10:55 pm - 1:05 amDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
6:55 pm - 9:10 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 15mnonstop
$297Southwest
Tue, Sep 15 - Sat, Sep 19
Delta Logo
3:59 pm - 10:44 pmDAL  Dallas Love Field-MDW Chicago Midway
6h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:30 pm - 9:57 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 27m1 stop Atlanta Hartsfield-Jackson
$317Delta
Sat, Oct 3 - Tue, Oct 6
Delta Logo
3:59 pm - 10:44 pmDAL  Dallas Love Field-MDW Chicago Midway
6h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 2:11 pmMDW  Chicago Midway-DAL Dallas Love Field
8h 07m1 stop Atlanta Hartsfield-Jackson
$317Delta
Booking Insights

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 from Dallas Love Field Airport to Chicago 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 start at $297. Prices are typical for this route right now, with typical round-trip fares ranging from $230 to $414. The lowest price found in the past 5 days was $297 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 $257 round-trip. Other Dallas Love Field Airport to Chicago routes average $332, 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?

Wednesday is the cheapest day of the week to fly from Dallas Love Field Airport to Chicago, it is 18% cheaper than the average day. Sunday is the most expensive day with flight prices 22% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is 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 ($395) and June ($373) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 99% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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

Flights from Dallas Love Field Airport to Chicago are cheapest 9 weeks before departure. Booking in this window typically costs about 45% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Dallas Love Field Airport to Chicago flights

Low season

December

Cheapest flight

$149
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 16% increase in price.
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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.

  • What airlines are available from Dallas Love Field Airport to Chicago?

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

  • 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 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 travelers should check the fare details before booking.

  • 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 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 $321 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.

  • 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) - 43% of one-stop connections
    • Orlando (MCO) - 14% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 14% of one-stop connections
    • Lambert-St Louis (STL) - 14% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

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

    Yes. Being flexible with your travel dates can save you up to 33% on the Dallas Love Field Airport to Chicago route. Wednesday is the cheapest departure day at $265 round-trip on average, while Sunday is the most expensive at $391, a difference of $126. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • 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%.

  • What popular places can I visit in Chicago?

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

  • 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 8:13 am
    • Latest: departs at 10:55 pm and lands at 1:08 am.

    The flight takes about 2h 13m.

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

    Last-minute fares on this route - booked within 2 weeks of departure - run 36% above the route average of $320. Book 9 weeks before departure for the lowest fares.

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

    A nonstop flight from Dallas Love Field Airport to Chicago takes 2h 13m, 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.

  • 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 $297 to $1,418. That means the highest observed fare was about 5x higher than the lowest one.

  • 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 $151, which is 29% below the typical average for this route.

  • 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 4h 02m via Fort Leonard Wood Waynesville Regional (TBN) and 4h 58m via Chicago O'Hare Intl (ORD).

  • 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
    · Dollar
    · Ace

    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 $30:

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

  • 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 $230 to $414, with an average of $320 over the past 12 months. Anything below $230 counts as a good deal.

  • 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.

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 can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $265 - about $126 less than Sunday (32% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 9 weeks before you fly. On this route, that window historically saves about 45% 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 $197 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 $144 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

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

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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Direct returns

Chicago to Dallas Love Field

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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

Information on your arrival and departure airports

Dallas Love Field (DAL)