$158+ 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
HRL — CHI
Jun 5 — Jun 121
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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Best
Last-minute
One-way
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 May 6, 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 May 6, 2026.
This Southwest deal was found by Cheapflights users on 5/4. 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.
Mon 6/16:55 am
HRL
- ORD
1 stop6h 20m
Southwest
Wed 6/33:45 pm
ORD
- HRL
1 stop5h 10m
Southwest
Deal found 5/4![Southwest logo]()
$269
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:45 pm
HRL
- ORD
1 stop5h 03m
American Airlines
Wed 5/275:00 am
ORD
- HRL
1 stop5h 13m
American Airlines
Deal found 5/1![American Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 5/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:16 pm
HRL
- ORD
1 stop6h 01m
United Airlines
Sun 9/66:30 am
ORD
- HRL
1 stop6h 44m
United Airlines
Deal found 5/3![United Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:20 pm
HRL
- ORD
1 stop5h 55m
United Airlines
Wed 5/272:05 pm
ORD
- HRL
1 stop7h 49m
United Airlines
Deal found 5/2![United Airlines logo]()
$301
This United Airlines deal was found by Cheapflights users on 5/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:18 pm
HRL
- ORD
1 stop7h 27m
United Airlines
Sat 5/162:09 pm
ORD
- HRL
1 stop7h 50m
United Airlines
Deal found 5/4![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 5/5. 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.
Thu 10/82:00 pm
HRL
- ORD
1 stop7h 34m
Delta
Sun 10/116:00 am
ORD
- HRL
1 stop7h 31m
Delta
Deal found 5/5![Delta logo]()
$313
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/24:57 pm
HRL
- ORD
1 stop6h 40m
American Airlines
Tue 6/95:00 am
ORD
- HRL
1 stop5h 13m
American Airlines
Deal found 5/5![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 6/124:57 pm
HRL
- ORD
1 stop7h 42m
American Airlines
Tue 6/165:00 am
ORD
- HRL
1 stop5h 13m
American Airlines
Deal found 5/5![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 5/1. 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.
Tue 5/1912:45 pm
HRL
- ORD
2 stops9h 10m
Southwest
Wed 5/2711:55 am
ORD
- HRL
1 stop5h 25m
Southwest
Deal found 5/1![Southwest logo]()
$336
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 May 6, 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 May 6, 2026.
This Southwest deal was found by Cheapflights users on 5/3. 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.
Mon 6/16:55 am
HRL
- ORD
1 stop6h 20m
Southwest
Wed 6/311:55 am
ORD
- HRL
1 stop5h 25m
Southwest
Deal found 5/3![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 5/5. 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.
Thu 10/82:00 pm
HRL
- ORD
1 stop7h 34m
Delta
Sun 10/116:00 am
ORD
- HRL
1 stop7h 31m
Delta
Deal found 5/5![Delta logo]()
$313
This American Airlines deal was found by Cheapflights users on 5/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:00 pm
HRL
- ORD
1 stop6h 39m
American Airlines
Sat 7/112:59 pm
ORD
- HRL
1 stop5h 13m
American Airlines
Deal found 5/3![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:16 pm
HRL
- ORD
1 stop6h 01m
United Airlines
Tue 9/227:30 am
ORD
- HRL
1 stop8h 04m
United Airlines
Deal found 5/3![United Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 5/1. 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.
Tue 5/197:10 am
HRL
- ORD
1 stop6h 05m
Southwest
Thu 5/284:15 pm
ORD
- HRL
2 stops6h 45m
Southwest
Deal found 5/1![Southwest logo]()
$398
Last-minute flights from Harlingen to ChicagoDiscover last-minute flight deals from Harlingen to Chicago. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Harlingen to Chicago. Data last updated May 6, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:18 pm
HRL
- ORD
1 stop7h 27m
United Airlines
Sat 5/162:09 pm
ORD
- HRL
1 stop7h 50m
United Airlines
Deal found 5/4![United Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:45 pm
HRL
- ORD
1 stop5h 03m
American Airlines
Wed 5/275:00 am
ORD
- HRL
1 stop5h 13m
American Airlines
Deal found 5/1![American Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 5/1. 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.
Tue 5/1912:45 pm
HRL
- ORD
2 stops9h 10m
Southwest
Wed 5/2711:55 am
ORD
- HRL
1 stop5h 25m
Southwest
Deal found 5/1![Southwest logo]()
$336
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:45 pm
HRL
- ORD
1 stop5h 03m
American Airlines
Tue 5/264:44 pm
ORD
- HRL
1 stop7h 30m
American Airlines
Deal found 5/1![American Airlines logo]()
$347
This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:20 pm
HRL
- ORD
1 stop5h 55m
United Airlines
Wed 5/272:05 pm
ORD
- HRL
1 stop7h 49m
United Airlines
Deal found 5/2![United Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 5/4. 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.
Mon 6/16:55 am
HRL
- ORD
1 stop6h 20m
Southwest
Wed 6/33:45 pm
ORD
- HRL
1 stop5h 10m
Southwest
Deal found 5/4![Southwest logo]()
$269
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/24:57 pm
HRL
- ORD
1 stop6h 40m
American Airlines
Tue 6/95:00 am
ORD
- HRL
1 stop5h 13m
American Airlines
Deal found 5/5![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 6/124:57 pm
HRL
- ORD
1 stop7h 42m
American Airlines
Tue 6/165:00 am
ORD
- HRL
1 stop5h 13m
American Airlines
Deal found 5/5![American Airlines logo]()
$329
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 May 6, 2026.
Search for one-way flight options from Harlingen to Chicago. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This United Airlines deal was found by Cheapflights users on 5/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:20 pm
HRL
- ORD
1 stop7h 25m
United Airlines
Deal found 5/3![United Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 5/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:00 pm
HRL
- ORD
1 stop7h 50m
American Airlines
Deal found 5/3![American Airlines logo]()
$170
This United Airlines deal was found by Cheapflights users on 5/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:20 pm
HRL
- ORD
1 stop7h 25m
United Airlines
Deal found 5/3![United Airlines logo]()
$205
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/166:00 am
HRL
- ORD
1 stop5h 08m
American Airlines
Deal found 5/5![American Airlines logo]()
$210
This American Airlines deal was found by Cheapflights users on 5/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:18 pm
HRL
- ORD
1 stop6h 21m
American Airlines
Deal found 5/3![American Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 5/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/14:57 pm
HRL
- ORD
1 stop7h 42m
American Airlines
Deal found 5/3![American Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 5/3. 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 5/236:05 am
HRL
- ORD
2 stops15h 50m
Southwest
Deal found 5/3![Southwest logo]()
$321
This United Airlines deal was found by Cheapflights users on 5/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:10 am
HRL
- ORD
2 stops13h 29m
United Airlines
Deal found 5/3![United Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 5/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:20 pm
HRL
- ORD
2 stops14h 07m
United Airlines
Deal found 5/3![United Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 5/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/98:04 pm
HRL
- ORD
2 stops12h 41m
American Airlines
Deal found 5/3![American Airlines logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/111:49 pm
HRL
- ORD
3 stops14h 52m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$619
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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (Southwest) |
One-way from | $158 (United Airlines) |
Popular in | January |
Cheapest in | August |
Average price | $321 |
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 May 6, 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 - ORD
HRLORD
Harlingen Valley Intl
Mon 6/1
6:55 am-1:15 pm
1 stop6h 20m
Chicago O'Hare Intl
Wed 6/3
11:55 am-5:20 pm
1 stop5h 25m
$269
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Thu 10/8
2:00 pm-9:34 pm
1 stop7h 34m
Chicago O'Hare Intl
Sun 10/11
6:00 am-1:31 pm
1 stop7h 31m
$313
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Tue 7/7
5:00 pm-11:39 pm
1 stop6h 39m
Chicago O'Hare Intl
Sat 7/11
2:59 pm-8:12 pm
1 stop5h 13m
$339
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Sat 9/19
5:16 pm-11:17 pm
1 stop6h 01m
Chicago O'Hare Intl
Tue 9/22
7:30 am-3:34 pm
1 stop8h 04m
$380
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Tue 5/19
7:10 am-1:15 pm
1 stop6h 05m
Chicago O'Hare Intl
Thu 5/28
4:15 pm-11:00 pm
2 stops6h 45m
$398
Cheapest one-way
Quickest one-way
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Tue 6/16
6:00 am-11:08 am
1 stop5h 08m
$210
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Sat 7/11
5:18 pm-11:39 pm
1 stop6h 21m
$215
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Sat 5/23
6:05 am-9:55 pm
2 stops15h 50m
$321
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Tue 6/16
5:10 am-8:25 pm
2 stops15h 15m
$321
HarlingenChicago
HRL - ORD
HRLORD
Harlingen Valley Intl
Fri 7/10
5:10 am-6:39 pm
2 stops13h 29m
$346
Showing 1-10 of 13 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 May.
| 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 May 6, 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.
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from 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 May 6, 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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Harlingen and Chicago flights
Browse other Harlingen and Chicago flight options. Last updated on May 6, 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 May 6, 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$393 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$252 | Average$328 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$259 | Average$438 | FlexibilityNo cancel fee | On-time71% |