$149+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — MDW
Sep 3 — Sep 101
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
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.Cheap flight deals from Love Field to Midway
Cheapest
Best
Last-minute
One-way
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 August 4, 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 August 4, 2026.
This Southwest deal was found by Cheapflights users on 7/30. 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 8/277:20 am -
Nonstop2h 15m
Thu 9/37:00 pm -
Nonstop2h 15m
Deal found 7/30![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 8/4. 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 9/55:00 pm -
Nonstop2h 15m
Sat 9/126:45 am -
Nonstop2h 10m
Deal found 8/4![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/3. 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 9/56:10 am -
1 stop5h 35m
Sun 9/67:35 am -
Nonstop2h 15m
Deal found 8/3![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 7/31. 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 9/265:00 pm -
Nonstop2h 15m
Tue 9/298:50 am -
2 stops5h 50m
Deal found 7/31![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 8/4. 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 9/112:55 pm -
Nonstop2h 10m
Sat 9/266:45 am -
Nonstop2h 10m
Deal found 8/4![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 8/2. 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 9/107:20 am -
Nonstop2h 15m
Sat 9/127:30 pm -
Nonstop2h 10m
Deal found 8/2![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 8/4. 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 9/55:00 pm -
Nonstop2h 15m
Tue 9/85:30 pm -
Nonstop2h 15m
Deal found 8/4![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 8/4. 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 9/102:55 pm -
Nonstop2h 10m
Tue 9/158:20 am -
Nonstop2h 20m
Deal found 8/4![Southwest logo]()
$317
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 August 4, 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 August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 9/55:00 pm -
Nonstop2h 15m
Sun 9/67:35 am -
Nonstop2h 15m
Deal found 8/2![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 7/30. 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 12/18:35 am -
1 stop3h 50m
Thu 12/1710:00 am -
Nonstop2h 25m
Deal found 7/30![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 8/3. 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 9/55:00 pm -
Nonstop2h 15m
Sat 9/126:45 am -
Nonstop2h 10m
Deal found 8/3![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 7/30. 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 9/229:50 am -
Nonstop2h 10m
Wed 9/308:50 am -
2 stops5h 50m
Deal found 7/30![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 8/3. 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 9/113:25 pm -
1 stop4h 00m
Mon 9/147:25 am -
Nonstop2h 10m
Deal found 8/3![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 8/3. 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 9/168:15 am -
Nonstop2h 15m
Mon 9/215:30 am -
Nonstop2h 10m
Deal found 8/3![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 8/1. 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.
Mon 8/242:55 pm -
Nonstop2h 10m
Thu 8/275:55 pm -
Nonstop2h 15m
Deal found 8/1![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 7/31. 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 10/226:00 am -
Nonstop2h 10m
Mon 10/267:15 am -
Nonstop2h 15m
Deal found 7/31![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 8/4. 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 9/165:05 pm -
Nonstop2h 10m
Sat 9/1910:05 am -
1 stop4h 00m
Deal found 8/4![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 8/4. 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 9/2612:10 pm -
Nonstop2h 10m
Wed 9/3010:30 am -
1 stop3h 45m
Deal found 8/4![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 7/31. 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 8/299:10 am -
1 stop5h 10m
Thu 9/35:30 am -
Nonstop2h 10m
Deal found 7/31![Southwest logo]()
$333
Last-minute flights from Love Field to MidwayDiscover last-minute flight deals from Love Field to Midway. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Love Field to Midway. Data last updated August 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/30. 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 8/277:20 am -
Nonstop2h 15m
Thu 9/37:00 pm -
Nonstop2h 15m
Deal found 7/30![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 8/4. 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 9/55:00 pm -
Nonstop2h 15m
Sat 9/126:45 am -
Nonstop2h 10m
Deal found 8/4![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/3. 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 9/56:10 am -
1 stop5h 35m
Sun 9/67:35 am -
Nonstop2h 15m
Deal found 8/3![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 8/4. 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 9/55:00 pm -
Nonstop2h 15m
Tue 9/85:30 pm -
Nonstop2h 15m
Deal found 8/4![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 8/2. 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 9/107:20 am -
Nonstop2h 15m
Sat 9/127:30 pm -
Nonstop2h 10m
Deal found 8/2![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 8/4. 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 9/102:55 pm -
Nonstop2h 10m
Tue 9/158:20 am -
Nonstop2h 20m
Deal found 8/4![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 8/4. 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 9/112:55 pm -
Nonstop2h 10m
Sat 9/266:45 am -
Nonstop2h 10m
Deal found 8/4![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 7/31. 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 9/265:00 pm -
Nonstop2h 15m
Tue 9/298:50 am -
2 stops5h 50m
Deal found 7/31![Southwest logo]()
$308
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 August 4, 2026.
Search for one-way flight options from Love Field to Midway. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/1. 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 9/55:00 pm -
Nonstop2h 15m
Deal found 8/1![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 7/31. 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 10/305:00 pm -
1 stop4h 10m
Deal found 7/31![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 8/3. 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 9/106:30 pm -
Nonstop2h 10m
Deal found 8/3![Southwest logo]()
$156
This Delta deal was found by Cheapflights users on 8/3. 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 9/52:57 pm -
1 stop7h 39m
Deal found 8/3![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 8/4. 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 10m
Deal found 8/4![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 8/4. 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 9/92:55 pm -
1 stop5h 15m
Deal found 8/4![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 8/3. 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 8/271:20 pm -
1 stop3h 35m
Deal found 8/3![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 8/4. 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 9/126:34 am -
2 stops10h 23m
Deal found 8/4![Delta logo]()
$171
This Southwest deal was found by Cheapflights users on 8/4. 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 8/2911:30 am -
1 stop4h 35m
Deal found 8/4![Southwest logo]()
$172
This Delta deal was found by Cheapflights users on 8/3. 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.
Wed 9/26:00 am -
2 stops10h 59m
Deal found 8/3![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 8/4. 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 9/32:55 pm -
Nonstop2h 10m
Deal found 8/4![Southwest logo]()
$185
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (Southwest) |
One-way from | $149 (Southwest) |
Popular in | January |
Cheapest in | December |
Average price | $372 |
Good round-trip deal | $359 or less |
Good one-way deal | $211 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 August 4, 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
Sat 9/5
5:00 pm-7:15 pm
Nonstop2h 15m
Chicago Midway
Sun 9/6
7:35 am-9:50 am
Nonstop2h 15m
$297
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Tue 12/1
8:35 am-12:25 pm
1 stop3h 50m
Chicago Midway
Thu 12/17
10:00 am-12:25 pm
Nonstop2h 25m
$303
Quickest round-trip
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Sat 9/5
5:00 pm-7:15 pm
Nonstop2h 15m
Chicago Midway
Sat 9/12
6:45 am-8:55 am
Nonstop2h 10m
$304
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Tue 9/22
9:50 am-12:00 pm
Nonstop2h 10m
Chicago Midway
Wed 9/30
8:50 am-2:40 pm
2 stops5h 50m
$308
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Fri 9/11
3:25 pm-7:25 pm
1 stop4h 00m
Chicago Midway
Mon 9/14
7:25 am-9:35 am
Nonstop2h 10m
$316
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Wed 9/16
8:15 am-10:30 am
Nonstop2h 15m
Chicago Midway
Mon 9/21
5:30 am-7:40 am
Nonstop2h 10m
$323
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Mon 8/24
2:55 pm-5:05 pm
Nonstop2h 10m
Chicago Midway
Thu 8/27
5:55 pm-8:10 pm
Nonstop2h 15m
$323
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 10/22
6:00 am-8:10 am
Nonstop2h 10m
Chicago Midway
Mon 10/26
7:15 am-9:30 am
Nonstop2h 15m
$323
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Wed 9/16
5:05 pm-7:15 pm
Nonstop2h 10m
Chicago Midway
Sat 9/19
10:05 am-2:05 pm
1 stop4h 00m
$329
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Sat 9/26
12:10 pm-2:20 pm
Nonstop2h 10m
Chicago Midway
Wed 9/30
10:30 am-2:15 pm
1 stop3h 45m
$329
Showing 1-10 of 20 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 August.
| 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 | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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 January is currently the most expensive (average of $487). 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 August 4, 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 15% 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 August 1, 2026.
Travelers seeking maximum savings on their Dallas Love Field Airport to Chicago Midway Airport flight should consider departing on Wednesday 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 August 4, 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.
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
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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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 August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$223 | Average$414 | FlexibilityNo cancel fee | On-time63% |