$100+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — DAL
May 11 — May 181
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 August, booked 51 days in advance, depart on a Thursday or Saturday and return on a Wednesday
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 April 11, 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 April 11, 2026.
This Southwest deal was found by Cheapflights users on 4/7. 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 5/910:15 am
MDW
- DAL
Nonstop2h 25m
Southwest
Tue 5/127:35 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/7![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 4/7. 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 5/93:05 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Mon 5/112:10 pm
DAL
- MDW
1 stop3h 50m
Southwest
Deal found 4/7![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 4/8. 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 4/3012:45 pm
MDW
- DAL
1 stop5h 10m
Southwest
Mon 5/47:05 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/8![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 4/7. 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 4/3012:45 pm
MDW
- DAL
1 stop5h 10m
Southwest
Sat 5/212:40 pm
DAL
- MDW
1 stop4h 10m
Southwest
Deal found 4/7![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 4/10. 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 5/128:45 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Wed 5/136:15 am
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/10![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 4/9. 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.
Thu 5/75:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Thu 5/149:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/9![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 4/7. 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 5/1610:15 am
MDW
- DAL
Nonstop2h 25m
Southwest
Sun 5/176:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 4/7![Southwest logo]()
$222
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 April 11, 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 April 11, 2026.
This Southwest deal was found by Cheapflights users on 4/7. 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 4/2910:05 am
MDW
- DAL
1 stop3h 45m
Southwest
Sat 5/23:15 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 4/7![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 4/8. 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 5/233:05 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Sat 6/66:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 4/8![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 4/10. 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 5/303:05 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Mon 6/19:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/10![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 4/6. 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 6/194:20 pm
MDW
- DAL
Nonstop2h 15m
Southwest
Mon 6/2210:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/6![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 4/7. 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 5/910:00 am
MDW
- DAL
2 stops6h 00m
Southwest
Sun 5/177:35 am
DAL
- MDW
1 stop4h 25m
Southwest
Deal found 4/7![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 4/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:25 pm
MDW
- DAL
1 stop5h 55m
Southwest
Wed 5/279:40 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 4/11![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 4/7. 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 6/207:40 am
MDW
- DAL
1 stop5h 50m
Southwest
Wed 6/249:55 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/7![Southwest logo]()
$258
This Southwest deal was found by Cheapflights users on 4/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/610:15 am
MDW
- DAL
1 stop4h 15m
Southwest
Tue 6/912:00 pm
DAL
- MDW
2 stops5h 00m
Southwest
Deal found 4/11![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 4/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:10 am
MDW
- DAL
2 stops5h 35m
Southwest
Sun 5/176:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 4/11![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 4/9. 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 6/210:05 am
MDW
- DAL
Nonstop2h 25m
Southwest
Thu 6/410:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/9![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 4/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Tue 5/267:35 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/11![Southwest logo]()
$285
Last-minute flights from Midway to Love FieldDiscover last-minute flight deals from Midway to Love Field. Data last updated April 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Love Field. Data last updated April 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/8. 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 4/3012:45 pm
MDW
- DAL
1 stop5h 10m
Southwest
Mon 5/47:05 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/8![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 4/7. 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 4/3012:45 pm
MDW
- DAL
1 stop5h 10m
Southwest
Sat 5/212:40 pm
DAL
- MDW
1 stop4h 10m
Southwest
Deal found 4/7![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 4/7. 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 5/28:10 am
MDW
- DAL
2 stops6h 35m
Southwest
Mon 5/47:45 pm
DAL
- MDW
1 stop4h 10m
Southwest
Deal found 4/7![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 4/7. 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 5/93:05 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Mon 5/117:05 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/7![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 4/7. 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 5/910:30 am
MDW
- DAL
1 stop3h 55m
Southwest
Tue 5/126:05 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 4/7![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 4/10. 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 5/128:45 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Wed 5/136:15 am
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 4/10![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 4/6. 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 5/145:00 pm
MDW
- DAL
Nonstop2h 30m
Southwest
Tue 5/196:05 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 4/6![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 4/7. 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 5/1610:15 am
MDW
- DAL
Nonstop2h 25m
Southwest
Sun 5/176:00 am
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 4/7![Southwest logo]()
$222
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 April 11, 2026.
Search for one-way flight options from Midway to Love Field. Find affordable one-way fares based on user searches. Data last updated April 11, 2026.
This Southwest deal was found by Cheapflights users on 4/7. 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 5/75:00 pm
MDW
- DAL
Nonstop2h 30m
Southwest
Deal found 4/7![Southwest logo]()
$100
This Southwest deal was found by Cheapflights users on 4/7. 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 5/610:25 am
MDW
- DAL
1 stop4h 30m
Southwest
Deal found 4/7![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 4/8. 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 6/305:05 am
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 4/8![Southwest logo]()
$109
This Southwest deal was found by Cheapflights users on 4/7. 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 5/28:10 am
MDW
- DAL
2 stops6h 35m
Southwest
Deal found 4/7![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 4/8. 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 5/1610:00 am
MDW
- DAL
2 stops6h 00m
Southwest
Deal found 4/8![Southwest logo]()
$115
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:53 pm
MDW
- DAL
1 stop5h 05m
Delta
Deal found 4/10![Delta logo]()
$119
This Delta deal was found by Cheapflights users on 4/7. 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.
Sat 5/96:23 am
MDW
- DAL
1 stop7h 44m
Delta
Deal found 4/7![Delta logo]()
$120
This Southwest deal was found by Cheapflights users on 4/9. 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 5/185:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 4/9![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 4/7. 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 5/87:20 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 4/7![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 4/10. 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 5/910:15 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 4/10![Southwest logo]()
$129
This Delta deal was found by Cheapflights users on 4/9. 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.
Thu 4/306:00 am
MDW
- DAL
1 stop5h 32m
Delta
Deal found 4/9![Delta logo]()
$130
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 April 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $199 (Southwest) |
One-way from | $100 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $384 |
Good round-trip deal | $277 or less |
Good one-way deal | $168 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 April 11, 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
Wed 4/29
10:05 am-1:50 pm
1 stop3h 45m
Dallas Love Field
Sat 5/2
3:15 pm-5:30 pm
Nonstop2h 15m
$205
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sat 5/23
3:05 pm-5:30 pm
Nonstop2h 25m
Dallas Love Field
Sat 6/6
6:00 am-8:15 am
Nonstop2h 15m
$227
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sat 5/30
3:05 pm-5:30 pm
Nonstop2h 25m
Dallas Love Field
Mon 6/1
9:45 pm-11:55 pm
Nonstop2h 10m
$245
Quickest round-trip
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Fri 6/19
4:20 pm-6:35 pm
Nonstop2h 15m
Dallas Love Field
Mon 6/22
10:50 pm-1:00 am
Nonstop2h 10m
$245
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sat 5/9
10:00 am-4:00 pm
2 stops6h 00m
Dallas Love Field
Sun 5/17
7:35 am-12:00 pm
1 stop4h 25m
$247
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sat 5/23
5:25 pm-11:20 pm
1 stop5h 55m
Dallas Love Field
Wed 5/27
9:40 am-11:55 am
Nonstop2h 15m
$255
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sat 6/20
7:40 am-1:30 pm
1 stop5h 50m
Dallas Love Field
Wed 6/24
9:55 pm-12:05 am
Nonstop2h 10m
$258
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Sat 6/6
10:15 am-2:30 pm
1 stop4h 15m
Dallas Love Field
Tue 6/9
12:00 pm-5:00 pm
2 stops5h 00m
$271
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Wed 5/13
10:10 am-3:45 pm
2 stops5h 35m
Dallas Love Field
Sun 5/17
6:00 am-8:15 am
Nonstop2h 15m
$273
ChicagoDallas
MDW - DAL
MDWDAL
Chicago Midway
Tue 6/2
10:05 am-12:30 pm
Nonstop2h 25m
Dallas Love Field
Thu 6/4
10:50 pm-1:00 am
Nonstop2h 10m
$279
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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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?
Use this chart to determine the optimal time to book a round-trip flight from Midway to Love Field. Price data was last updated on April 10, 2026.
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 51 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, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Dallas Love Field Airport (average of $133). Flying from Chicago Midway Airport to Dallas Love Field Airport in May is currently the most expensive (average of $225). 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 April 11, 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 28% 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 April 4, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Dallas Love Field Airport flight should consider departing on Tuesday evenings 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 April 11, 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.
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
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 April 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$160 | Average$323 | FlexibilityNo cancel fee | On-time63% |