$109+ Cheap flights from Harlingen (HRL) to Chicago (CHI)
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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
Sep 11 — Sep 181
Round-trip
1 adult, Economy
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Find cheap flights from Harlingen to Chicago 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 Harlingen to Chicago
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Cheapest flights from Harlingen to ChicagoExplore the most affordable flight options available from Harlingen to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.
Explore the most affordable flight options available from Harlingen to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:18 pm -
1 stop7h 41m
Tue 9/224:11 pm -
1 stop5h 41m
Deal found 8/11![United Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:18 pm -
1 stop6h 08m
Sat 9/124:11 pm -
1 stop5h 41m
Deal found 8/10![United Airlines logo]()
$220
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:46 pm -
1 stop6h 44m
Sat 10/173:50 pm -
1 stop7h 00m
Deal found 8/10![American Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:43 pm -
1 stop5h 35m
Sat 9/53:54 pm -
1 stop7h 00m
Deal found 8/12![American Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:43 pm -
1 stop5h 35m
Mon 8/315:00 am -
1 stop5h 04m
Deal found 8/10![American Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:59 pm -
1 stop6h 06m
Sat 9/1912:47 pm -
1 stop6h 52m
Deal found 8/11![United Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:45 am -
1 stop7h 40m
Tue 9/225:00 am -
1 stop4h 58m
Deal found 8/9![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:53 pm -
1 stop7h 21m
Sat 9/2612:09 pm -
1 stop4h 49m
Deal found 8/12![American Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:13 pm -
2 stops9h 39m
Mon 11/26:20 am -
1 stop7h 03m
Deal found 8/7![Delta logo]()
$344
Best flights from Harlingen to ChicagoDiscover carefully curated flight deals from Harlingen to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 12, 2026.
Discover carefully curated flight deals from Harlingen to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 12, 2026.
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:43 pm -
1 stop5h 35m
Mon 8/313:54 pm -
1 stop7h 00m
Deal found 8/7![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:05 am -
2 stops13h 25m
Tue 9/2210:40 am -
1 stop5h 19m
Deal found 8/11![United Airlines logo]()
$384
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:18 pm -
1 stop7h 41m
Sat 9/58:10 pm -
2 stops19h 49m
Deal found 8/10![United Airlines logo]()
$489
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:05 am -
2 stops10h 33m
Sat 9/268:45 am -
1 stop7h 14m
Deal found 8/11![United Airlines logo]()
$493
This United Airlines deal was found by Cheapflights users on 8/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:05 am -
2 stops10h 33m
Tue 10/278:40 am -
2 stops11h 07m
Deal found 8/12![United Airlines logo]()
$497
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:59 pm -
1 stop7h 33m
Mon 8/318:10 pm -
2 stops17h 14m
Deal found 8/7![United Airlines logo]()
$520
This United Airlines deal was found by Cheapflights users on 8/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:18 pm -
1 stop7h 05m
Thu 10/159:20 pm -
2 stops18h 39m
Deal found 8/12![United Airlines logo]()
$520
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:18 pm -
1 stop7h 41m
Mon 9/77:45 pm -
2 stops20h 14m
Deal found 8/11![United Airlines logo]()
$558
Last-minute flights from Harlingen to ChicagoDiscover last-minute flight deals from Harlingen to Chicago. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Harlingen to Chicago. Data last updated August 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:43 pm -
1 stop5h 35m
Mon 8/315:00 am -
1 stop5h 04m
Deal found 8/10![American Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:43 pm -
1 stop5h 35m
Sat 9/53:54 pm -
1 stop7h 00m
Deal found 8/12![American Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/11:59 pm -
1 stop7h 33m
Sat 9/56:30 am -
1 stop6h 54m
Deal found 8/11![United Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:18 pm -
1 stop6h 08m
Sat 9/124:11 pm -
1 stop5h 41m
Deal found 8/10![United Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:59 pm -
1 stop6h 06m
Sat 9/1912:47 pm -
1 stop6h 52m
Deal found 8/11![United Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:18 pm -
1 stop7h 41m
Tue 9/224:11 pm -
1 stop5h 41m
Deal found 8/11![United Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:45 am -
1 stop7h 40m
Tue 9/225:00 am -
1 stop4h 58m
Deal found 8/9![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:53 pm -
1 stop7h 21m
Sat 9/2612:09 pm -
1 stop4h 49m
Deal found 8/12![American Airlines logo]()
$325
One-way flights from Harlingen to ChicagoSearch for one-way flight options from Harlingen to Chicago. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
Search for one-way flight options from Harlingen to Chicago. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Delta deal was found by Cheapflights users on 8/12. 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 10/102:13 pm -
1 stop7h 23m
Deal found 8/12![Delta logo]()
$109
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:59 pm -
1 stop6h 06m
Deal found 8/11![United Airlines logo]()
$112
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:13 pm -
2 stops9h 39m
Deal found 8/10![Delta logo]()
$114
This Delta deal was found by Cheapflights users on 8/12. 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 10/142:13 pm -
1 stop7h 23m
Deal found 8/12![Delta logo]()
$121
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:18 pm -
1 stop6h 08m
Deal found 8/11![United Airlines logo]()
$130
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:30 pm -
2 stops9h 29m
Deal found 8/11![Delta logo]()
$135
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/82:49 pm -
1 stop7h 11m
Deal found 8/12![American Airlines logo]()
$149
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:59 pm -
1 stop6h 06m
Deal found 8/11![United Airlines logo]()
$154
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/72:13 pm -
1 stop7h 23m
Deal found 8/10![Delta logo]()
$156
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:18 pm -
1 stop7h 41m
Deal found 8/11![United Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/32:47 pm -
1 stop7h 28m
Deal found 8/8![American Airlines logo]()
$159
Find flight deals from Harlingen to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Harlingen (HRL) to Chicago (CHI). 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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (United Airlines) |
One-way from | $109 (Delta) |
Popular in | January |
Cheapest in | August |
Average price | $294 |
Cheapflights Fare Finder
Customize your flight search to find flights from Harlingen to Chicago 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 12, 2026.
Use the filters below to find and compare flights from Harlingen to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Wed 8/26
6:43 pm-12:18 am
1 stop5h 35m
Chicago O'Hare Intl
Mon 8/31
3:54 pm-10:54 pm
1 stop7h 00m
$354
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Tue 9/15
5:05 am-6:30 pm
2 stops13h 25m
Chicago O'Hare Intl
Tue 9/22
10:40 am-3:59 pm
1 stop5h 19m
$384
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Tue 9/1
5:18 pm-12:59 am
1 stop7h 41m
Chicago O'Hare Intl
Sat 9/5
8:10 pm-3:59 pm
2 stops19h 49m
$489
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Thu 9/24
5:05 am-3:38 pm
2 stops10h 33m
Chicago O'Hare Intl
Sat 9/26
8:45 am-3:59 pm
1 stop7h 14m
$493
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Tue 10/13
5:05 am-3:38 pm
2 stops10h 33m
Chicago O'Hare Intl
Tue 10/27
8:40 am-7:47 pm
2 stops11h 07m
$497
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Wed 8/26
1:59 pm-9:32 pm
1 stop7h 33m
Chicago O'Hare Intl
Mon 8/31
8:10 pm-1:24 pm
2 stops17h 14m
$520
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Mon 10/12
5:18 pm-12:23 am
1 stop7h 05m
Chicago O'Hare Intl
Thu 10/15
9:20 pm-3:59 pm
2 stops18h 39m
$520
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Fri 9/4
5:18 pm-12:59 am
1 stop7h 41m
Chicago O'Hare Intl
Mon 9/7
7:45 pm-3:59 pm
2 stops20h 14m
$558
Cheapest one-way
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Sat 9/12
1:59 pm-8:05 pm
1 stop6h 06m
$154
HarlingenChicago
HRL Harlingen Valley Intl - ORD Chicago O'Hare Intl
HRLORD
Harlingen Valley Intl
Sat 10/10
2:13 pm-9:36 pm
1 stop7h 23m
$156
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Harlingen to Chicago
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 Harlingen to Chicago in August.
| 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 Harlingen-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Harlingen-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Harlingen-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Harlingen-Chicago 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 Harlingen-Chicago 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 Harlingen to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Harlingen with our price prediction graph.
HRL-CHI
HRL-ORD
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 Harlingen to Chicago
HRL-CHI
HRL-ORD
What is the cheapest month to book a flight from Harlingen to Chicago?
Currently, May is the cheapest month in which you can book a flight from Harlingen to Chicago (average of $298). Flying from Harlingen to Chicago in March is currently the most expensive (average of $540). 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.
How much does it cost to fly round-trip from Harlingen to Chicago?
Airfare is below average for this route at the moment.
Harlingen to Chicago flights typically cost between $284 and $294 in September.The cheapest round-trip price found within the last 5 days was $217 on United Airlines (Sep 15-Sep 22).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 12, 2026.
Read through reviews of airlines operating flights from Harlingen to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Harlingen to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 12, 2026.
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Harlingen and Chicago flights
Browse other Harlingen and Chicago flight options. Last updated on August 12, 2026.
Other flights from Harlingen
Browse through other flights departing from Harlingen. Flights are based on user searches made on Cheapflights and were last updated on August 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Harlingen to Chicago
Discover the top 2 airlines that operate flights from Harlingen to Chicago. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$417 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$288 | Average$348 | FlexibilityNo cancel fee | On-time71% |