$117+ Cheap flights from Love Field (DAL) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — MDW
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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Find cheap flights from Love Field to Midway 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
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Cheapest flights from Love Field to MidwayExplore the most affordable flight options available from Love Field to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
Explore the most affordable flight options available from Love Field to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
This Southwest deal was found by Cheapflights users on 9/16. 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 10/136:25 pm -
Nonstop2h 15m
Tue 10/204:45 pm -
Nonstop2h 15m
Deal found 9/16![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 9/16. 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 10/136:25 pm -
Nonstop2h 15m
Sat 10/172:20 pm -
1 stop3h 55m
Deal found 9/16![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/16. 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 10/144:40 pm -
Nonstop2h 20m
Wed 10/213:30 pm -
1 stop4h 00m
Deal found 9/16![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:00 am -
1 stop6h 05m
Tue 10/209:20 pm -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 9/17. 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 10/2411:35 am -
1 stop3h 45m
Tue 10/273:30 pm -
1 stop4h 00m
Deal found 9/17![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 9/17. 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 10/281:20 pm -
1 stop3h 50m
Sat 10/3110:20 am -
1 stop3h 30m
Deal found 9/17![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 9/16. 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 10/69:35 pm -
Nonstop2h 15m
Sat 11/76:20 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 9/17. 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 10/206:35 am -
1 stop4h 20m
Wed 10/2110:10 am -
1 stop4h 40m
Deal found 9/17![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 9/17. 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 10/247:00 am -
Nonstop2h 10m
Mon 10/267:15 am -
Nonstop2h 15m
Deal found 9/17![Southwest logo]()
$255
Best flights from Love Field to MidwayDiscover carefully curated flight deals from Love Field to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
Discover carefully curated flight deals from Love Field to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
This Southwest deal was found by Cheapflights users on 9/16. 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 10/139:35 pm -
Nonstop2h 15m
Sat 10/172:20 pm -
1 stop3h 55m
Deal found 9/16![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:00 am -
1 stop4h 45m
Tue 10/202:50 pm -
Nonstop2h 15m
Deal found 9/17![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 9/16. 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 11/26:50 pm -
Nonstop2h 10m
Tue 11/38:45 pm -
Nonstop2h 25m
Deal found 9/16![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 9/19. 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 10/2210:55 pm -
Nonstop2h 15m
Mon 10/266:25 pm -
1 stop4h 30m
Deal found 9/19![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/19. 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 10/106:20 pm -
Nonstop2h 20m
Wed 10/145:40 am -
Nonstop2h 15m
Deal found 9/19![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/20. 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 10/197:35 pm -
1 stop4h 55m
Mon 10/265:50 pm -
1 stop3h 30m
Deal found 9/20![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 9/16. 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 10/167:15 pm -
Nonstop2h 10m
Fri 10/234:15 pm -
1 stop4h 25m
Deal found 9/16![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:20 pm -
Nonstop2h 20m
Sun 10/188:30 am -
Nonstop2h 15m
Deal found 9/17![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 9/20. 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 11/16:40 am -
Nonstop2h 10m
Tue 11/33:45 pm -
1 stop4h 10m
Deal found 9/20![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 9/20. 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 11/306:55 pm -
Nonstop2h 10m
Thu 12/38:50 am -
Nonstop2h 30m
Deal found 9/20![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 9/20. 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 10/281:20 pm -
1 stop3h 50m
Sun 11/12:35 pm -
1 stop4h 20m
Deal found 9/20![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 9/18. 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 11/2610:20 am -
Nonstop2h 15m
Mon 11/303:40 pm -
Nonstop2h 30m
Deal found 9/18![Southwest logo]()
$383
Last-minute flights from Love Field to MidwayDiscover last-minute flight deals from Love Field to Midway. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Love Field to Midway. Data last updated September 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/16. 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 10/69:35 pm -
Nonstop2h 15m
Sat 11/76:20 pm -
Nonstop2h 35m
Deal found 9/16![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 9/16. 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 10/136:25 pm -
Nonstop2h 15m
Tue 10/204:45 pm -
Nonstop2h 15m
Deal found 9/16![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 9/16. 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 10/132:50 pm -
1 stop4h 35m
Sat 10/172:20 pm -
1 stop3h 55m
Deal found 9/16![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 9/16. 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 10/144:40 pm -
Nonstop2h 20m
Wed 10/213:30 pm -
1 stop4h 00m
Deal found 9/16![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:00 am -
1 stop6h 05m
Sat 10/246:35 am -
Nonstop2h 15m
Deal found 9/17![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:00 am -
1 stop6h 05m
Tue 10/2012:15 pm -
1 stop5h 00m
Deal found 9/17![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 9/17. 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 10/206:35 am -
1 stop4h 20m
Wed 10/2110:10 am -
1 stop4h 40m
Deal found 9/17![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 9/17. 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 10/2411:35 am -
1 stop3h 45m
Tue 10/273:30 pm -
1 stop4h 00m
Deal found 9/17![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 9/17. 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 10/247:00 am -
Nonstop2h 10m
Mon 10/267:15 am -
Nonstop2h 15m
Deal found 9/17![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 9/17. 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 10/281:20 pm -
1 stop3h 50m
Sat 10/3110:20 am -
1 stop3h 30m
Deal found 9/17![Southwest logo]()
$246
One-way flights from Love Field to MidwaySearch for one-way flight options from Love Field to Midway. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
Search for one-way flight options from Love Field to Midway. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Southwest deal was found by Cheapflights users on 9/16. 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 10/289:35 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 9/16. 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 10/1711:35 am -
1 stop3h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 9/16. 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 10/271:20 pm -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 9/16. 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 10/106:00 am -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 9/16. 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 11/146:06 am -
2 stops10h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$132
This Southwest deal was found by Cheapflights users on 9/16. 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 11/510:55 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$135
This Delta deal was found by Cheapflights users on 9/17. 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 12/176:06 am -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$146
This Southwest deal was found by Cheapflights users on 9/17. 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 10/810:55 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 9/18. 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 10/203:59 pm -
1 stop6h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$149
Find flight deals from Love Field to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Love Field (DAL) to Midway (MDW). 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 September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $233 (Southwest) |
One-way from | $117 (Southwest) |
Popular in | September |
Cheapest in | December |
Average price | $519 |
Good round-trip deal | $383 or less |
Good one-way deal | $228 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Love Field to Midway 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 7,457,451 searches. Data last updated September 21, 2026.
Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Mon 11/2
6:50 pm-9:00 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Tue 10/27
8:05 pm-10:20 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Wed 11/4
8:25 pm-10:40 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Sat 10/17
11:35 am-3:20 pm
1 stop3h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Fri 10/9
10:55 pm-1:10 am
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Fri 10/16
10:55 pm-1:10 am
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$152
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Sat 11/21
3:15 pm-8:25 pm
1 stop5h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Tue 10/13
9:35 pm-11:50 pm
Nonstop2h 15m
Chicago Midway
Sat 10/17
2:20 pm-6:15 pm
1 stop3h 55m
$239
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Sat 10/17
6:00 am-10:45 am
1 stop4h 45m
Chicago Midway
Tue 10/20
2:50 pm-5:05 pm
Nonstop2h 15m
$243
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Mon 11/2
6:50 pm-9:00 pm
Nonstop2h 10m
Chicago Midway
Tue 11/3
8:45 pm-11:10 pm
Nonstop2h 25m
$251
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Love Field to Midway
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 Love Field to Midway in September.
| 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 Dallas Love Field Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Dallas Love Field Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Dallas Love Field Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Dallas Love Field Airport-Chicago Midway 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 Dallas Love Field Airport-Chicago Midway 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 Love Field to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Love Field with our price prediction graph.
DAL-MDW
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 Dallas Love Field Airport to Chicago Midway Airport
What is the cheapest month to book a flight from Dallas Love Field Airport to Chicago Midway Airport?
Currently, December is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago Midway Airport (average of $186). Flying from Dallas Love Field Airport to Chicago Midway Airport in September is currently the most expensive (average of $519). 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 DAL to MDW?
Find hourly flight availability from Love Field to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 21, 2026.
One of the essential ways to save on airfare from Dallas Love Field Airport to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 12% on airfare.
What is the cheapest day to fly from Dallas Love Field Airport to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Love Field to Midway. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Dallas Love Field Airport to Chicago Midway Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 21, 2026.
Get a feel of what it's like to fly with Southwest from Dallas Love Field Airport to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Love Field to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Love Field to Midway
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 21, 2026.
Love Field and Midway flights
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Other flights from Love Field
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Top airline flying from Love Field to Midway
Discover the top airline that operate flights from Love Field to Midway. 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 7,457,451 searches. Data last updated September 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$233 | Average$434 | FlexibilityNo cancel fee | On-time63% |