$96+ Cheap flights from Midway (MDW) to Love Field (DAL)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — DAL
Aug 12 — Aug 191
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Love Field with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago Midway to Dallas Love Field are usually found in September or December, booked 30 days in advance, depart on a Thursday or Friday and return on a Saturday
Cheap flight deals from Midway to Love Field
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to Love FieldExplore the most affordable flight options available from Midway to Love Field. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 13, 2026.
Explore the most affordable flight options available from Midway to Love Field. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:55 am
MDW
- DAL
2 stops5h 00m
Southwest
Mon 8/316:00 am
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/10![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:30 am
MDW
- DAL
Nonstop2h 10m
Southwest
Sat 8/228:30 am
DAL
- MDW
2 stops5h 45m
Southwest
Deal found 7/10![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:50 am
MDW
- DAL
2 stops5h 50m
Southwest
Thu 8/203:25 pm
DAL
- MDW
1 stop4h 00m
Southwest
Deal found 7/10![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:30 am
MDW
- DAL
Nonstop2h 10m
Southwest
Tue 9/296:30 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/8![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:10 pm
MDW
- DAL
1 stop5h 16m
Delta
Mon 8/106:00 am
DAL
- MDW
1 stop5h 51m
Delta
Deal found 7/8![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:05 am
MDW
- DAL
1 stop4h 40m
Southwest
Sat 8/2211:30 am
DAL
- MDW
1 stop4h 35m
Southwest
Deal found 7/8![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:50 am
MDW
- DAL
2 stops5h 50m
Southwest
Tue 9/88:40 am
DAL
- MDW
1 stop4h 50m
Southwest
Deal found 7/8![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:40 pm
MDW
- DAL
Nonstop2h 10m
Southwest
Mon 8/311:20 pm
DAL
- MDW
1 stop3h 35m
Southwest
Deal found 7/8![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:29 am
MDW
- DAL
2 stops12h 28m
Delta
Sat 9/263:59 pm
DAL
- MDW
1 stop6h 46m
Delta
Deal found 7/8![Delta logo]()
$216
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:30 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Mon 9/219:10 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/8![Southwest logo]()
$218
Best flights from Midway to Love FieldDiscover carefully curated flight deals from Midway to Love Field that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 13, 2026.
Discover carefully curated flight deals from Midway to Love Field that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:50 am
MDW
- DAL
Nonstop2h 15m
Southwest
Fri 9/186:30 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/9![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:05 am
MDW
- DAL
1 stop5h 19m
Delta
Tue 9/83:59 pm
DAL
- MDW
1 stop6h 46m
Delta
Deal found 7/11![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:55 am
MDW
- DAL
2 stops5h 00m
Southwest
Mon 8/109:10 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/8![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:50 am
MDW
- DAL
2 stops5h 50m
Southwest
Fri 9/113:25 pm
DAL
- MDW
1 stop4h 00m
Southwest
Deal found 7/9![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/43:30 pm
MDW
- DAL
1 stop4h 40m
Southwest
Mon 10/57:15 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/8![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:15 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Tue 8/111:10 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/12![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:10 am
MDW
- DAL
Nonstop2h 10m
Southwest
Wed 9/26:30 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/12![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:30 am
MDW
- DAL
1 stop4h 15m
Southwest
Sun 8/167:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/9![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:40 pm
MDW
- DAL
1 stop4h 45m
Southwest
Sun 8/236:10 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/10![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:55 am
MDW
- DAL
2 stops5h 00m
Southwest
Tue 8/257:40 am
DAL
- MDW
1 stop4h 10m
Southwest
Deal found 7/12![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:40 pm
MDW
- DAL
1 stop4h 45m
Southwest
Sun 9/207:55 am
DAL
- MDW
1 stop4h 50m
Southwest
Deal found 7/10![Southwest logo]()
$326
Last-minute flights from Midway to Love FieldDiscover last-minute flight deals from Midway to Love Field. Data last updated July 13, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Love Field. Data last updated July 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:30 am
MDW
- DAL
Nonstop2h 10m
Southwest
Sat 8/228:30 am
DAL
- MDW
2 stops5h 45m
Southwest
Deal found 7/10![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:10 pm
MDW
- DAL
1 stop5h 16m
Delta
Mon 8/106:00 am
DAL
- MDW
1 stop5h 51m
Delta
Deal found 7/8![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:55 am
MDW
- DAL
2 stops5h 00m
Southwest
Mon 8/105:20 pm
DAL
- MDW
1 stop5h 00m
Southwest
Deal found 7/9![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:30 am
MDW
- DAL
1 stop4h 15m
Southwest
Sat 8/155:00 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/9![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:30 am
MDW
- DAL
Nonstop2h 10m
Southwest
Mon 8/177:20 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 7/9![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:05 am
MDW
- DAL
1 stop4h 40m
Southwest
Sat 8/2211:30 am
DAL
- MDW
1 stop4h 35m
Southwest
Deal found 7/8![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:50 am
MDW
- DAL
2 stops5h 50m
Southwest
Thu 8/203:25 pm
DAL
- MDW
1 stop4h 00m
Southwest
Deal found 7/10![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:55 am
MDW
- DAL
2 stops5h 00m
Southwest
Mon 8/316:00 am
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 7/10![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:40 pm
MDW
- DAL
Nonstop2h 10m
Southwest
Mon 8/311:20 pm
DAL
- MDW
1 stop3h 35m
Southwest
Deal found 7/8![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:55 am
MDW
- DAL
2 stops5h 00m
Southwest
Sat 8/298:30 am
DAL
- MDW
2 stops5h 45m
Southwest
Deal found 7/10![Southwest logo]()
$221
One-way flights from Midway to Love FieldSearch for one-way flight options from Midway to Love Field. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
Search for one-way flight options from Midway to Love Field. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:30 am
MDW
- DAL
Nonstop2h 10m
Southwest
Deal found 7/10![Southwest logo]()
$96
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:30 am
MDW
- DAL
1 stop3h 45m
Southwest
Deal found 7/9![Southwest logo]()
$101
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:30 am
MDW
- DAL
1 stop3h 45m
Southwest
Deal found 7/8![Southwest logo]()
$102
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:10 pm
MDW
- DAL
1 stop5h 16m
Delta
Deal found 7/9![Delta logo]()
$106
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:50 am
MDW
- DAL
2 stops5h 50m
Southwest
Deal found 7/8![Southwest logo]()
$107
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:55 am
MDW
- DAL
2 stops5h 50m
Southwest
Deal found 7/10![Southwest logo]()
$112
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:25 am
MDW
- DAL
Nonstop2h 10m
Southwest
Deal found 7/8![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/103:20 pm
MDW
- DAL
1 stop5h 00m
Southwest
Deal found 7/8![Southwest logo]()
$124
Find flight deals from Midway to Love Field
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Love Field (DAL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $206 (Southwest) |
One-way from | $96 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $444 |
Good round-trip deal | $372 or less |
Good one-way deal | $184 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Love Field that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 13, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Dallas Love Field Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Tue 9/15
9:50 am-12:05 pm
Nonstop2h 15m
Dallas Love Field
Fri 9/18
6:30 pm-8:40 pm
Nonstop2h 10m
$218
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Mon 8/10
5:55 am-10:55 am
2 stops5h 00m
Dallas Love Field
Mon 8/10
9:10 pm-11:20 pm
Nonstop2h 10m
$225
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Tue 9/8
8:50 am-2:40 pm
2 stops5h 50m
Dallas Love Field
Fri 9/11
3:25 pm-7:25 pm
1 stop4h 00m
$289
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sun 10/4
3:30 pm-8:10 pm
1 stop4h 40m
Dallas Love Field
Mon 10/5
7:15 pm-9:25 pm
Nonstop2h 10m
$294
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Thu 9/3
6:05 am-11:24 am
1 stop5h 19m
Dallas Love Field
Tue 9/8
3:59 pm-10:45 pm
1 stop6h 46m
$295
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Wed 8/5
5:15 pm-7:30 pm
Nonstop2h 15m
Dallas Love Field
Tue 8/11
1:10 pm-3:20 pm
Nonstop2h 10m
$297
Quickest round-trip
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Wed 8/26
11:10 am-1:20 pm
Nonstop2h 10m
Dallas Love Field
Wed 9/2
6:30 pm-8:40 pm
Nonstop2h 10m
$297
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Mon 8/10
5:30 am-9:45 am
1 stop4h 15m
Dallas Love Field
Sun 8/16
7:45 pm-9:55 pm
Nonstop2h 10m
$312
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Fri 8/21
1:40 pm-6:25 pm
1 stop4h 45m
Dallas Love Field
Sun 8/23
6:10 pm-8:20 pm
Nonstop2h 10m
$317
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Thu 8/20
5:55 am-10:55 am
2 stops5h 00m
Dallas Love Field
Tue 8/25
7:40 am-11:50 am
1 stop4h 10m
$322
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Midway to Love Field
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Love Field in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Dallas Love Field Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Dallas Love Field Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Dallas Love Field Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Dallas Love Field Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Dallas Love Field Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Love Field
Have a flexible travel schedule? Discover the best time to fly to Love Field from Midway with our price prediction graph.
MDW-DAL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Dallas Love Field Airport
How far ahead should I book a flight from Chicago Midway Airport to Dallas Love Field Airport?
The price you pay for your flight from Chicago Midway Airport to Dallas Love Field Airport may vary depending on when you book. For the best chance of a lower fare, look to book 29 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago Midway Airport to Dallas Love Field Airport?
Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Dallas Love Field Airport (average of $247). Flying from Chicago Midway Airport to Dallas Love Field Airport in March is currently the most expensive (average of $483). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to DAL?
Find hourly flight availability from Midway to Love Field. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 13, 2026.
It’s optimal to fly from Chicago Midway Airport to Dallas Love Field Airport in the evening. By choosing this option you can save up to 27% on the cost of your flight, compared to a flight in the afternoon.
What is the cheapest day to fly from Chicago Midway Airport to Dallas Love Field Airport?
Use this chart to determine the cheapest time to fly round-trip from Midway to Love Field. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Dallas Love Field Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Love Field
Get insights into the airlines that provide service to Love Field. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Love Field. Reviews last updated July 13, 2026.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Dallas Love Field Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentIla,Mar 2025
HOU - DAL
Related info for your journey
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Top airline flying from Midway to Love Field
Discover the top airline that operate flights from Midway to Love Field. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$191 | Average$386 | FlexibilityNo cancel fee | On-time63% |