$100+ Cheap flights from Love Field (DAL) to Midway (MDW)
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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — MDW
May 2 — May 91
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 April 2, 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 April 2, 2026.
This Southwest deal was found by Cheapflights users on 3/31. 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 4/309:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 5/23:05 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 3/31![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/31. 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 4/309:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Thu 5/710:10 am
MDW
- DAL
1 stop4h 40m
Southwest
Deal found 3/31![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 3/30. 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 6/19:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Wed 6/175:05 am
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 3/30![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 3/30. 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 5/202:40 pm
DAL
- MDW
1 stop5h 00m
Southwest
Wed 5/275:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 3/30![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 3/31. 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 5/51:30 pm
DAL
- MDW
1 stop3h 20m
Southwest
Sat 5/910:30 am
MDW
- DAL
1 stop3h 55m
Southwest
Deal found 3/31![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 3/30. 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 4/214:35 pm
DAL
- MDW
1 stop3h 35m
Southwest
Wed 4/2210:10 am
MDW
- DAL
2 stops5h 35m
Southwest
Deal found 3/30![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 3/29. 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 5/197:12 am
DAL
- MDW
1 stop4h 44m
Delta
Tue 5/265:12 pm
MDW
- DAL
1 stop6h 44m
Delta
Deal found 3/29![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 3/31. 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 6/17:20 pm
DAL
- MDW
1 stop4h 10m
Southwest
Thu 6/46:20 pm
MDW
- DAL
1 stop4h 40m
Southwest
Deal found 3/31![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 4/1. 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 5/26:15 am
DAL
- MDW
2 stops5h 55m
Southwest
Thu 5/712:45 pm
MDW
- DAL
1 stop4h 10m
Southwest
Deal found 4/1![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 4/1. 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 5/236:50 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Thu 5/285:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 4/1![Southwest logo]()
$221
This Southwest deal was found by Cheapflights users on 3/31. 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 5/17:05 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 5/23:05 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 3/31![Southwest logo]()
$222
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 April 2, 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 April 2, 2026.
This Southwest deal was found by Cheapflights users on 3/28. 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 5/52:45 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Sat 5/910:15 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 3/28![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 4/2. 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 5/76:20 am
DAL
- MDW
Nonstop2h 10m
Southwest
Tue 5/125:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 4/2![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/31. 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 5/49:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Thu 5/710:20 am
MDW
- DAL
1 stop3h 45m
Southwest
Deal found 3/31![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 3/28. 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 4/306:20 am
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 5/28:10 am
MDW
- DAL
2 stops6h 35m
Southwest
Deal found 3/28![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 3/30. 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 4/2311:05 am
DAL
- MDW
1 stop3h 50m
Southwest
Mon 4/2710:20 am
MDW
- DAL
1 stop3h 45m
Southwest
Deal found 3/30![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 3/29. 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 5/1311:15 am
DAL
- MDW
1 stop3h 40m
Southwest
Mon 5/184:00 pm
MDW
- DAL
1 stop5h 00m
Southwest
Deal found 3/29![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 3/29. 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 5/287:20 pm
DAL
- MDW
1 stop4h 10m
Southwest
Mon 6/14:00 pm
MDW
- DAL
1 stop5h 00m
Southwest
Deal found 3/29![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 3/29. 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 6/34:35 pm
DAL
- MDW
1 stop3h 35m
Southwest
Sat 6/66:30 am
MDW
- DAL
Nonstop2h 20m
Southwest
Deal found 3/29![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 3/29. 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 5/87:05 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Mon 5/114:00 pm
MDW
- DAL
1 stop5h 00m
Southwest
Deal found 3/29![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 3/31. 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 5/17:45 pm
DAL
- MDW
1 stop4h 10m
Southwest
Mon 5/45:55 pm
MDW
- DAL
1 stop4h 55m
Southwest
Deal found 3/31![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 3/31. 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 7/3010:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sun 8/25:00 am
MDW
- DAL
Nonstop2h 15m
Southwest
Deal found 3/31![Southwest logo]()
$245
Last-minute flights from Love Field to MidwayDiscover last-minute flight deals from Love Field to Midway. Data last updated April 2, 2026 and is based on user searches.
Discover last-minute flight deals from Love Field to Midway. Data last updated April 2, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/30. 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 4/214:35 pm
DAL
- MDW
1 stop3h 35m
Southwest
Wed 4/2210:10 am
MDW
- DAL
2 stops5h 35m
Southwest
Deal found 3/30![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 3/31. 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 4/309:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 5/23:05 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 3/31![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/31. 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 4/309:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Thu 5/710:10 am
MDW
- DAL
1 stop4h 40m
Southwest
Deal found 3/31![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 3/31. 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 5/17:05 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Sat 5/23:05 pm
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 3/31![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 3/30. 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 5/210:17 am
DAL
- MDW
1 stop6h 09m
Delta
Wed 5/65:21 pm
MDW
- DAL
1 stop5h 12m
Delta
Deal found 3/30![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 4/1. 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 5/26:15 am
DAL
- MDW
2 stops5h 55m
Southwest
Thu 5/712:45 pm
MDW
- DAL
1 stop4h 10m
Southwest
Deal found 4/1![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 3/31. 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 5/26:15 am
DAL
- MDW
2 stops5h 55m
Southwest
Mon 5/49:00 am
MDW
- DAL
1 stop4h 00m
Southwest
Deal found 3/31![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 3/31. 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 5/51:30 pm
DAL
- MDW
1 stop3h 20m
Southwest
Sat 5/910:30 am
MDW
- DAL
1 stop3h 55m
Southwest
Deal found 3/31![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 3/29. 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 5/197:12 am
DAL
- MDW
1 stop4h 44m
Delta
Wed 5/276:23 am
MDW
- DAL
1 stop5h 12m
Delta
Deal found 3/29![Delta logo]()
$218
This Southwest deal was found by Cheapflights users on 3/30. 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 5/202:40 pm
DAL
- MDW
1 stop5h 00m
Southwest
Wed 5/275:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 3/30![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 4/1. 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 5/236:50 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Thu 5/285:30 am
MDW
- DAL
Nonstop2h 25m
Southwest
Deal found 4/1![Southwest logo]()
$221
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 April 2, 2026.
Search for one-way flight options from Love Field to Midway. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
This Southwest deal was found by Cheapflights users on 3/31. 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 4/282:45 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 3/31![Southwest logo]()
$100
This Southwest deal was found by Cheapflights users on 3/30. 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 5/211:00 am
DAL
- MDW
1 stop3h 35m
Southwest
Deal found 3/30![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 3/31. 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 6/167:50 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 3/31![Southwest logo]()
$109
This Southwest deal was found by Cheapflights users on 3/31. 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 6/3012:00 pm
DAL
- MDW
1 stop3h 55m
Southwest
Deal found 3/31![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 3/29. 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 5/236:50 pm
DAL
- MDW
Nonstop2h 15m
Southwest
Deal found 3/29![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 3/31. 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 5/229:45 pm
DAL
- MDW
Nonstop2h 10m
Southwest
Deal found 3/31![Southwest logo]()
$123
This Southwest deal was found by Cheapflights users on 3/31. 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 5/3012:40 pm
DAL
- MDW
1 stop4h 10m
Southwest
Deal found 3/31![Southwest logo]()
$128
This Delta deal was found by Cheapflights users on 3/29. 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 5/266:00 am
DAL
- MDW
1 stop5h 56m
Delta
Deal found 3/29![Delta logo]()
$130
This Delta deal was found by Cheapflights users on 3/31. 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.
Fri 5/293:59 pm
DAL
- MDW
1 stop5h 10m
Delta
Deal found 3/31![Delta logo]()
$133
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 April 2, 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 | October |
Cheapest in | December |
Average price | $251 |
Good round-trip deal | $257 or less |
Good one-way deal | $207 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 2,558,603 searches. Data last updated April 2, 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
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Tue 5/5
2:45 pm-5:00 pm
Nonstop2h 15m
Chicago Midway
Sat 5/9
10:15 am-12:40 pm
Nonstop2h 25m
$199
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 5/7
6:20 am-8:30 am
Nonstop2h 10m
Chicago Midway
Tue 5/12
5:30 am-7:55 am
Nonstop2h 25m
$199
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Mon 5/4
9:45 pm-11:55 pm
Nonstop2h 10m
Chicago Midway
Thu 5/7
10:20 am-2:05 pm
1 stop3h 45m
$205
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 4/30
6:20 am-8:30 am
Nonstop2h 10m
Chicago Midway
Sat 5/2
8:10 am-2:45 pm
2 stops6h 35m
$210
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 4/23
11:05 am-2:55 pm
1 stop3h 50m
Chicago Midway
Mon 4/27
10:20 am-2:05 pm
1 stop3h 45m
$214
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Wed 5/13
11:15 am-2:55 pm
1 stop3h 40m
Chicago Midway
Mon 5/18
4:00 pm-9:00 pm
1 stop5h 00m
$219
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 5/28
7:20 pm-11:30 pm
1 stop4h 10m
Chicago Midway
Mon 6/1
4:00 pm-9:00 pm
1 stop5h 00m
$219
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Wed 6/3
4:35 pm-8:10 pm
1 stop3h 35m
Chicago Midway
Sat 6/6
6:30 am-8:50 am
Nonstop2h 20m
$228
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Fri 5/8
7:05 pm-9:15 pm
Nonstop2h 10m
Chicago Midway
Mon 5/11
4:00 pm-9:00 pm
1 stop5h 00m
$232
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Fri 5/1
7:45 pm-11:55 pm
1 stop4h 10m
Chicago Midway
Mon 5/4
5:55 pm-10:50 pm
1 stop4h 55m
$242
Showing 1-10 of 22 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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 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, April is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago Midway Airport (average of $147). Flying from Dallas Love Field Airport to Chicago Midway Airport in January is currently the most expensive (average of $278). 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 April 2, 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 at noon tend to be the most expensive. A flight in the evening could potentially save you up to 22% 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 March 28, 2026.
Travelers seeking maximum savings on their Dallas Love Field Airport to Chicago Midway Airport flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday afternoons 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 April 2, 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.
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Love Field and Midway flights
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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 2,558,603 searches. Data last updated April 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$166 | Average$308 | FlexibilityNo cancel fee | On-time63% |