$205+ Cheap flights from Midway (MDW) to Harlingen (HRL)
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.
MDW — HRL
Nov 22 — Nov 291
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to Harlingen 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 Midway to Harlingen
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to HarlingenExplore the most affordable flight options available from Midway to Harlingen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
Explore the most affordable flight options available from Midway to Harlingen. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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 12/146:40 am -
1 stop5h 30m
Mon 12/218:35 pm -
1 stop4h 25m
Deal found 10/23![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 10/19. 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.
Wed 11/1110:15 am -
2 stops10h 30m
Sat 11/1412:45 pm -
1 stop5h 25m
Deal found 10/19![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 10/21. 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 11/46:40 am -
1 stop5h 30m
Wed 11/114:30 pm -
1 stop6h 40m
Deal found 10/21![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 10/21. 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 11/195:00 pm -
1 stop4h 50m
Thu 11/261:25 pm -
1 stop4h 30m
Deal found 10/21![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 10/21. 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 11/55:15 am -
1 stop4h 55m
Tue 11/106:20 am -
1 stop6h 05m
Deal found 10/21![Southwest logo]()
$419
Best flights from Midway to HarlingenDiscover carefully curated flight deals from Midway to Harlingen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
Discover carefully curated flight deals from Midway to Harlingen that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
This Southwest deal was found by Cheapflights users on 10/22. 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 1/215:25 am -
1 stop6h 55m
Mon 1/254:40 pm -
1 stop4h 20m
Deal found 10/22![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 10/19. 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.
Fri 1/16:30 am -
1 stop5h 40m
Wed 1/67:40 am -
1 stop4h 55m
Deal found 10/19![Southwest logo]()
$258
This Southwest deal was found by Cheapflights users on 10/22. 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 1/16:30 am -
1 stop5h 40m
Thu 1/71:00 pm -
2 stops8h 20m
Deal found 10/22![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 10/21. 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 11/197:35 am -
2 stops8h 15m
Thu 11/261:25 pm -
1 stop4h 30m
Deal found 10/21![Southwest logo]()
$384
This Southwest deal was found by Cheapflights users on 10/21. 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 11/55:15 am -
1 stop4h 55m
Tue 11/106:20 am -
1 stop6h 05m
Deal found 10/21![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 10/21. 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 11/64:30 pm -
1 stop5h 00m
Tue 11/1011:35 am -
1 stop5h 35m
Deal found 10/21![Southwest logo]()
$446
Last-minute flights from Midway to HarlingenDiscover last-minute flight deals from Midway to Harlingen. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Harlingen. Data last updated October 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/21. 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 11/46:40 am -
1 stop5h 30m
Wed 11/114:30 pm -
1 stop6h 40m
Deal found 10/21![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 10/21. 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 11/55:15 am -
1 stop4h 55m
Tue 11/106:20 am -
1 stop6h 05m
Deal found 10/21![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 10/21. 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 11/64:30 pm -
1 stop5h 00m
Tue 11/1011:35 am -
1 stop5h 35m
Deal found 10/21![Southwest logo]()
$446
This Southwest deal was found by Cheapflights users on 10/19. 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.
Wed 11/1110:15 am -
2 stops10h 30m
Sat 11/1412:45 pm -
1 stop5h 25m
Deal found 10/19![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 10/21. 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 11/195:00 pm -
1 stop4h 50m
Thu 11/261:25 pm -
1 stop4h 30m
Deal found 10/21![Southwest logo]()
$378
One-way flights from Midway to HarlingenSearch for one-way flight options from Midway to Harlingen. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
Search for one-way flight options from Midway to Harlingen. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Southwest deal was found by Cheapflights users on 10/22. 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 10/285:25 pm -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 10/22. 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 11/410:15 am -
2 stops10h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 10/21. 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 11/197:35 am -
2 stops8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 10/20. 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 12/216:30 am -
1 stop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 12/223:40 pm -
2 stops8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sat 12/195:05 am -
1 stop5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$290
Find flight deals from Midway to Harlingen
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Harlingen (HRL). 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 October 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $235 (Southwest) |
One-way from | $205 (Southwest) |
Popular in | October |
Cheapest in | May |
Average price | $518 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Harlingen 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 October 23, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Harlingen that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Wed 10/28
5:25 pm-10:00 pm
1 stop4h 35m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$205
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Thu 11/19
7:35 am-3:50 pm
2 stops8h 15m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$220
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Mon 12/21
6:30 am-11:10 am
1 stop4h 40m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Wed 11/4
6:40 am-12:10 pm
1 stop5h 30m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Thu 1/21
5:25 am-12:20 pm
1 stop6h 55m
Harlingen Valley Intl
Mon 1/25
4:40 pm-9:00 pm
1 stop4h 20m
$235
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Fri 1/1
6:30 am-12:10 pm
1 stop5h 40m
Harlingen Valley Intl
Wed 1/6
7:40 am-12:35 pm
1 stop4h 55m
$258
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Tue 12/22
3:40 pm-12:10 am
2 stops8h 30m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$270
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Sat 12/19
5:05 am-10:50 am
1 stop5h 45m
Harlingen Valley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$290
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Fri 1/1
6:30 am-12:10 pm
1 stop5h 40m
Harlingen Valley Intl
Thu 1/7
1:00 pm-9:20 pm
2 stops8h 20m
$293
ChicagoHarlingen
MDW Chicago Midway - HRL Harlingen Valley Intl
MDWHRL
Chicago Midway
Thu 11/19
7:35 am-3:50 pm
2 stops8h 15m
Harlingen Valley Intl
Thu 11/26
1:25 pm-5:55 pm
1 stop4h 30m
$384
Showing 1-10 of 12 resultsSorted by cheapest first
Compare providers for flights from Midway to Harlingen
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 Harlingen in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Harlingen 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-Harlingen flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Harlingen flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Harlingen 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-Harlingen 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 Harlingen
Have a flexible travel schedule? Discover the best time to fly to Harlingen from Midway with our price prediction graph.
MDW-HRL
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.
Reviews of airlines servicing Harlingen
Get insights into the airlines that provide service to Harlingen. 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 Harlingen. Reviews last updated October 23, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Harlingen, such as Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.4
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.4
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Harlingen. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Harlingen flight routes
Other flight options
Other flights from Midway
Popular flights
Alternative routes for Midway to Harlingen
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Harlingen by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Harlingen by cabin class
Find flights from Midway to Harlingen, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Harlingen
Explore flights to Harlingen departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 23, 2026.
Midway and Harlingen flights
Browse other Midway and Harlingen flight options. Last updated on October 23, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on October 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Harlingen
Discover the top airline that operate flights from Midway to Harlingen. 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 October 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$403 | FlexibilityNo cancel fee | On-time63% |