$141+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
jul. 23 — jul. 301
Round-trip
1 adult, Economy
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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 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 juni 23, 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 juni 23, 2026.
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 8/106:43 pm
HRL
- ORD
1 stop5h 35m
American Airlines
di 8/185:00 am
ORD
- HRL
1 stop5h 04m
American Airlines
Deal found 6/18![American Airlines logo]()
$272
This American Airlines deal was found by Cheapflights users on 6/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 8/153:17 pm
HRL
- ORD
1 stop5h 59m
American Airlines
di 8/185:00 am
ORD
- HRL
1 stop5h 04m
American Airlines
Deal found 6/21![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vr 7/244:58 pm
HRL
- ORD
1 stop7h 52m
American Airlines
di 7/285:00 am
ORD
- HRL
1 stop5h 12m
American Airlines
Deal found 6/22![American Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 6/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
do 9/175:18 pm
HRL
- ORD
1 stop7h 41m
United Airlines
za 9/192:16 pm
ORD
- HRL
1 stop5h 23m
United Airlines
Deal found 6/23![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
do 10/82:00 pm
HRL
- ORD
1 stop7h 34m
Delta
zo 10/116:00 am
ORD
- HRL
1 stop7h 31m
Delta
Deal found 6/22![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 9/55:18 pm
HRL
- ORD
1 stop7h 41m
United Airlines
zo 9/67:30 am
ORD
- HRL
1 stop5h 54m
United Airlines
Deal found 6/22![United Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vr 7/244:58 pm
HRL
- ORD
1 stop7h 52m
American Airlines
za 8/111:00 am
ORD
- HRL
1 stop5h 45m
American Airlines
Deal found 6/22![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 8/155:18 pm
HRL
- ORD
1 stop6h 08m
United Airlines
di 8/188:50 am
ORD
- HRL
1 stop7h 09m
United Airlines
Deal found 6/22![United Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 7/204:58 pm
HRL
- ORD
1 stop7h 52m
American Airlines
ma 7/275:00 am
ORD
- HRL
1 stop5h 12m
American Airlines
Deal found 6/22![American Airlines logo]()
$366
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 juni 23, 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 juni 23, 2026.
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
wo 11/182:00 pm
HRL
- ORD
1 stop7h 34m
Delta
di 12/16:00 am
ORD
- HRL
1 stop7h 31m
Delta
Deal found 6/18![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 9/55:18 pm
HRL
- ORD
1 stop7h 41m
United Airlines
zo 9/67:30 am
ORD
- HRL
1 stop5h 54m
United Airlines
Deal found 6/22![United Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vr 7/244:58 pm
HRL
- ORD
1 stop7h 52m
American Airlines
di 7/285:00 am
ORD
- HRL
1 stop5h 12m
American Airlines
Deal found 6/22![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 6/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vr 9/115:18 pm
HRL
- ORD
1 stop6h 09m
United Airlines
zo 9/136:30 am
ORD
- HRL
1 stop6h 54m
United Airlines
Deal found 6/23![United Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 8/155:18 pm
HRL
- ORD
1 stop6h 08m
United Airlines
di 8/188:50 am
ORD
- HRL
1 stop7h 09m
United Airlines
Deal found 6/18![United Airlines logo]()
$363
This United Airlines deal was found by Cheapflights users on 6/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 8/115:18 pm
HRL
- ORD
1 stop6h 08m
United Airlines
ma 8/176:30 am
ORD
- HRL
1 stop6h 54m
United Airlines
Deal found 6/20![United Airlines logo]()
$396
This American Airlines deal was found by Cheapflights users on 6/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vr 7/244:58 pm
HRL
- ORD
1 stop7h 52m
American Airlines
za 8/111:00 am
ORD
- HRL
1 stop5h 45m
American Airlines
Deal found 6/19![American Airlines logo]()
$539
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 7/42:05 pm
HRL
- ORD
1 stop7h 35m
United Airlines
wo 7/84:05 pm
ORD
- HRL
1 stop5h 49m
United Airlines
Deal found 6/18![United Airlines logo]()
$481
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 7/115:10 am
HRL
- ORD
1 stop5h 52m
United Airlines
wo 7/155:30 am
ORD
- HRL
1 stop8h 00m
United Airlines
Deal found 6/22![United Airlines logo]()
$580
Last-minute flights from Harlingen to ChicagoDiscover last-minute flight deals from Harlingen to Chicago. Data last updated juni 23, 2026 and is based on user searches.
Discover last-minute flight deals from Harlingen to Chicago. Data last updated juni 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 6/294:57 pm
HRL
- ORD
1 stop7h 42m
American Airlines
za 7/45:00 am
ORD
- HRL
1 stop5h 12m
American Airlines
Deal found 6/22![American Airlines logo]()
$450
This United Airlines deal was found by Cheapflights users on 6/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 6/295:20 pm
HRL
- ORD
1 stop7h 25m
United Airlines
zo 7/55:30 am
ORD
- HRL
1 stop8h 00m
United Airlines
Deal found 6/20![United Airlines logo]()
$644
This United Airlines deal was found by Cheapflights users on 6/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 6/295:20 pm
HRL
- ORD
1 stop7h 25m
United Airlines
ma 7/64:05 pm
ORD
- HRL
1 stop5h 49m
United Airlines
Deal found 6/20![United Airlines logo]()
$716
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 6/304:57 pm
HRL
- ORD
1 stop7h 42m
American Airlines
za 7/45:00 am
ORD
- HRL
1 stop5h 12m
American Airlines
Deal found 6/22![American Airlines logo]()
$410
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 6/304:57 pm
HRL
- ORD
1 stop7h 42m
American Airlines
zo 8/95:00 am
ORD
- HRL
1 stop5h 04m
American Airlines
Deal found 6/18![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
do 7/26:00 am
HRL
- ORD
1 stop5h 10m
American Airlines
wo 7/85:00 am
ORD
- HRL
1 stop5h 12m
American Airlines
Deal found 6/18![American Airlines logo]()
$761
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
do 7/26:00 am
HRL
- ORD
1 stop5h 10m
American Airlines
zo 7/55:00 am
ORD
- HRL
1 stop5h 12m
American Airlines
Deal found 6/18![American Airlines logo]()
$791
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vr 7/310:45 am
HRL
- ORD
1 stop7h 31m
American Airlines
wo 7/85:00 am
ORD
- HRL
1 stop5h 12m
American Airlines
Deal found 6/18![American Airlines logo]()
$509
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 juni 23, 2026.
Search for one-way flight options from Harlingen to Chicago. Find affordable one-way fares based on user searches. Data last updated juni 23, 2026.
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 8/15:18 pm
HRL
- ORD
1 stop6h 21m
American Airlines
Deal found 6/22![American Airlines logo]()
$141
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 7/42:05 pm
HRL
- ORD
1 stop7h 35m
United Airlines
Deal found 6/18![United Airlines logo]()
$162
This United Airlines deal was found by Cheapflights users on 6/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
zo 6/285:10 am
HRL
- ORD
1 stop5h 20m
United Airlines
Deal found 6/22![United Airlines logo]()
$202
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 7/257:20 am
HRL
- ORD
1 stop5h 09m
United Airlines
Deal found 6/21![United Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 6/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
do 7/304:58 pm
HRL
- ORD
1 stop7h 52m
American Airlines
Deal found 6/19![American Airlines logo]()
$270
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
zo 7/265:10 am
HRL
- ORD
1 stop5h 51m
United Airlines
Deal found 6/21![United Airlines logo]()
$288
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 8/17:20 am
HRL
- ORD
2 stops25h 52m
United Airlines
Deal found 6/21![United Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vr 7/310:45 am
HRL
- ORD
1 stop7h 31m
American Airlines
Deal found 6/18![American Airlines logo]()
$310
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 juni 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (United Airlines) |
One-way from | $141 (American Airlines) |
Popular in | June |
Cheapest in | November |
Average price | $518 |
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 juni 23, 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
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
wo 11/18
2:00 pm-9:34 pm
1 stop7h 34m
Chicago O'Hare Intl
di 12/1
6:00 am-1:31 pm
1 stop7h 31m
$257
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
za 9/5
5:18 pm-12:59 am
1 stop7h 41m
Chicago O'Hare Intl
zo 9/6
7:30 am-1:24 pm
1 stop5h 54m
$315
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
vr 9/11
5:18 pm-11:27 pm
1 stop6h 09m
Chicago O'Hare Intl
zo 9/13
6:30 am-1:24 pm
1 stop6h 54m
$329
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
vr 7/24
4:58 pm-12:50 am
1 stop7h 52m
Chicago O'Hare Intl
di 7/28
5:00 am-10:12 am
1 stop5h 12m
$359
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
za 8/15
5:18 pm-11:26 pm
1 stop6h 08m
Chicago O'Hare Intl
di 8/18
8:50 am-3:59 pm
1 stop7h 09m
$363
Quickest round-trip
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
di 8/11
5:18 pm-11:26 pm
1 stop6h 08m
Chicago O'Hare Intl
ma 8/17
6:30 am-1:24 pm
1 stop6h 54m
$396
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
za 7/4
2:05 pm-9:40 pm
1 stop7h 35m
Chicago O'Hare Intl
wo 7/8
4:05 pm-9:54 pm
1 stop5h 49m
$481
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
vr 7/24
4:58 pm-12:50 am
1 stop7h 52m
Chicago O'Hare Intl
za 8/1
11:00 am-4:45 pm
1 stop5h 45m
$539
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
za 7/11
5:10 am-11:02 am
1 stop5h 52m
Chicago O'Hare Intl
wo 7/15
5:30 am-1:30 pm
1 stop8h 00m
$580
Cheapest one-way
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
za 7/4
2:05 pm-9:40 pm
1 stop7h 35m
$162
Showing 1-10 of 15 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 June.
| 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, October is the cheapest month in which you can book a flight from Harlingen to Chicago (average of $130). Flying from Harlingen to Chicago in March is currently the most expensive (average of $377). 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?
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 juni 23, 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.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
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 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
Lansing
Merrillville
Hammond
Porter
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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 juni 23, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Harlingen to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Harlingen and Chicago flights
Browse other Harlingen and Chicago flight options. Last updated on juni 23, 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 juni 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Harlingen to Chicago
Discover the top 3 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 juni 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$408 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$252 | Average$427 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$318 | Average$438 | FlexibilityNo cancel fee | On-time71% |