MDW

$109 Find Cheap Flights from Dallas to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$170
Typical prices: $164-$362
Frontier
Fri 11/23Tue 11/27
DFW - MDW • Non-stop
Cheapest one-way
$110
Typical prices: $113-$241
Frontier
Fri 11/16
DFW - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest and Frontier. Average duration is 2h 14m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 24% average savings
Most popular
Insights
Insights
Avoid delays
Most punctual • 75% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 10 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 39% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $176 (round-trip)
Shortest trip • 6h 06m (one-way)
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Dallas to Midway

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

Recent round-trip flight deals from Dallas to Midway

Mon, Nov 23 - Fri, Nov 27
Frontier Logo
5:01 am - 7:23 amDFW  Dallas/Fort Worth-MDW Chicago Midway
2h 22mnonstop
Frontier Logo
8:51 am - 11:36 amMDW  Chicago Midway-DFW Dallas/Fort Worth
2h 45mnonstop
$170Frontier
Thu, Nov 12 - Tue, Nov 17
Frontier Logo
8:54 am - 11:25 amDFW  Dallas/Fort Worth-MDW Chicago Midway
2h 31mnonstop
Frontier Logo
6:08 am - 12:13 pmMDW  Chicago Midway-DFW Dallas/Fort Worth
6h 05m1 stop Atlanta Hartsfield-Jackson
$170Frontier
Fri, Jan 22 - Mon, Jan 25
Frontier Logo
9:51 am - 12:13 pmDFW  Dallas/Fort Worth-MDW Chicago Midway
2h 22mnonstop
Frontier Logo
1:18 pm - 7:30 pmMDW  Chicago Midway-DFW Dallas/Fort Worth
6h 12m1 stop Atlanta Hartsfield-Jackson
$171Frontier
Fri, Feb 19 - Sat, Feb 27
Frontier Logo
9:51 am - 12:13 pmDFW  Dallas/Fort Worth-MDW Chicago Midway
2h 22mnonstop
Frontier Logo
1:18 pm - 11:01 pmMDW  Chicago Midway-DFW Dallas/Fort Worth
9h 43m1 stop Atlanta Hartsfield-Jackson
$171Frontier
Tue, Dec 15 - Tue, Dec 15
Southwest Logo
8:45 am - 11:00 amDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
3:30 pm - 5:55 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
$199Southwest
Wed, Dec 2 - Wed, Dec 9
Southwest Logo
8:25 pm - 10:40 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:50 am - 11:20 amMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$199Southwest
Tue, Dec 15 - Wed, Dec 16
Southwest Logo
8:45 am - 11:00 amDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$199Southwest
Sat, Dec 5 - Sat, Dec 5
Delta Logo
6:20 am - 11:59 amDFW  Dallas/Fort Worth-MDW Chicago Midway
5h 39m1 stop Minneapolis St Paul
Delta Logo
4:08 pm - 9:55 pmMDW  Chicago Midway-DFW Dallas/Fort Worth
5h 47m1 stop Atlanta Hartsfield-Jackson
$219Delta
Tue, Dec 1 - Wed, Dec 2
Delta Logo
7:15 am - 12:04 pmDFW  Dallas/Fort Worth-MDW Chicago Midway
4h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 11:16 amMDW  Chicago Midway-DFW Dallas/Fort Worth
5h 16m1 stop Atlanta Hartsfield-Jackson
$219Delta
Wed, Dec 9 - Sat, Dec 12
Delta Logo
6:12 am - 12:04 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 52m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 2:17 pmMDW  Chicago Midway-DAL Dallas Love Field
8h 17m1 stop Atlanta Hartsfield-Jackson
$219Delta
Booking Insights

Price, demand and travel trends for Dallas to Chicago Midway Airport 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 to Chicago Midway Airport?

Round-trip flights from Dallas to Chicago Midway Airport typically range from $164 to $362. The lowest price found in the past 5 days was $170, on Frontier.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Dallas to Chicago Midway Airport. It’s 4% cheaper than the average day, while Sunday is the most expensive, with prices 32% higher.

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

•February is the cheapest month to fly from Dallas to Chicago Midway Airport at $154 round-trip.
•September ($311) and June ($304) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 101% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Dallas to Chicago Midway Airport the cheapest?

Flights from Dallas to Chicago Midway Airport are cheapest 10 weeks before departure. Booking in this window typically costs about 43% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Dallas to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Key details for Dallas to Chicago Midway Airport flights

Low season

February

Cheapest flight

$110
Beat the crowds with an average 29% drop in travelers.
The most popular month to fly with an average 38% increase in travelers.
One-way flight from Dallas/Fort Worth Airport to Chicago Midway Airport

When to book flights from Dallas to Midway

Are your dates flexible? Find out the best times to travel from Dallas to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Dallas to Chicago Midway Airport 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 to Chicago Midway Airport?

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

    • Earliest: departs at 5:01 am and lands at 7:15 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 to Chicago Midway Airport?

    Three cabin classes are available on flights from Dallas to Chicago Midway Airport:

    • Economy Class
    • Premium Economy Class
    • Business Class

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

    A nonstop flight from Dallas to Chicago Midway Airport takes 2h 14m, covering 795 miles.

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

    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 to Chicago Midway Airport flight?

    Round-trip flights from Dallas to Chicago Midway Airport range from $164 to $362, with an average of $252 over the past 12 months. Anything below $164 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 29% above the $252 route average. Book 10 weeks before departure for the lowest fares.

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

    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 $252 for nonstop.

  • How does on-time performance compare across airlines flying from Dallas to Chicago Midway Airport?

    Frontier is the only airline operating Dallas to Chicago Midway Airport flights. 75% of its flights are on time.

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

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$100 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 to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Dallas to Chicago Midway Airport flights, with 43% of flights leaving in that window. Afternoon departures account for 29%, evening flights for 28%, and night flights for 0%.

  • Have flight prices from Dallas to Chicago Midway Airport 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 $170 to $1,227. That means the highest observed fare was about 7x higher than the lowest one.

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

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

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

    One-way fares from Dallas to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $110, which is 36% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

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

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

    Flights from Dallas to Chicago Midway Airport may depart from several airports in Dallas area, including Dallas Addison (ADS), Dallas Love Field (DAL) and Dallas/Fort Worth (DFW). Flights usually arrive at Chicago Midway (MDW).

  • What time of day has the fewest delays on flights from Dallas to Chicago Midway Airport?

    Morning flights have the fewest delays on this route, while night departures tend to have the most.

  • At what point is a flight considered delayed from Dallas to Chicago Midway Airport?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Dallas to Chicago Midway Airport route, 25% of flights were delayed in the past 3 months, with delays averaging 2h 33m.

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

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

    • Atlanta Hartsfield-Jackson (ATL) - 70% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 20% of one-stop connections
    • Lambert-St Louis (STL) - 10% of one-stop connections

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

    Yes. Flexible dates can save you up to 28% on flights from Dallas to Chicago Midway Airport. Wednesday is the cheapest departure day at $243 round-trip on average, while Sunday is the most expensive at $334, a difference of $91.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Dallas to Chicago Midway Airport?

    2 airlines operate flights between Dallas and Chicago Midway Airport. The airlines offering nonstop flights on this route include:

    • Southwest
    • Frontier

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

    Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 3h 40m, compared with 6h 06m via Detroit Metropolitan Wayne County (DTW) and 6h 19m via Atlanta Hartsfield-Jackson (ATL).

  • What popular places can I visit in Chicago Midway Airport?

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

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

    Among airlines operating Dallas to Chicago Midway Airport flights:

    • Frontier: offers free seat selection
    • 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 to Chicago Midway Airport flights?

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

    • Frontier: a cabin bag and a checked bag in Economy Class
    • 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 to Chicago Midway Airport 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 Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $243, about $91 less than Sunday fares (27% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 10 weeks before you fly. On this route, that window historically saves about 43% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Dallas to Chicago Midway Airport trip for February. Fares historically average $154 round-trip in that month - typically $157 less than the most expensive month, which is September (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 $76 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 Chicago Midway Airport

Prefer to fly direct from Dallas to Chicago Midway Airport?

 
Find which airlines fly direct from Dallas to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Dallas to Chicago Midway

Monday

Frontier,Southwest

Frontier,Southwest

Tuesday

Frontier,Southwest

Frontier,Southwest

Wednesday

Frontier,Southwest

Frontier,Southwest

Thursday

Frontier,Southwest

Frontier,Southwest

Friday

Frontier,Southwest

Frontier,Southwest

Saturday

Frontier,Southwest

Frontier,Southwest

Sunday

Frontier,Southwest

Frontier,Southwest

See more direct flights

Direct returns

Chicago Midway to Dallas

Monday

Frontier,Southwest

Frontier,Southwest

Tuesday

Frontier,Southwest

Frontier,Southwest

Wednesday

Frontier,Southwest

Frontier,Southwest

Thursday

Frontier,Southwest

Frontier,Southwest

Friday

Frontier,Southwest

Frontier,Southwest

Saturday

Frontier,Southwest

Frontier,Southwest

Sunday

Frontier,Southwest

Frontier,Southwest

See more direct flights

More options for your flight from Dallas to Midway

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