Title: Chicago to Harlingen cheap flights from $138 (CHI to HRL) - Expedia.com ![Beach condos, hotel with swimming pool, boardwalk access to sandy shoreline tropical South Beach, South Padre Island, exquisite barrier Gulf Coast of Texas, people enjoy beach activities aerial](https://images.trvl-media.com/place/1515/72916b6c-9126-4460-883a-7e0e2c7f43c5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/1515/72916b6c-9126-4460-883a-7e0e2c7f43c5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $138 Cheap Flights from Chicago (CHI) to Harlingen (HRL) [View $138 flight on Wed, Jun 3, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:ORD,to:HRL,departure:6/3/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:137.20&airProductToken=AQpoCjIIwYIBEgQzMDUyGK4cIKOxASjw3I4DMI3ejgM4QkAAWAFqBUJBU0lDcghRV0FaVU5CVgoyCMGCARIEMzU3NRijsQEgp1woqt-OAzCF4I4DOEJAAVgBagVCQVNJQ3IIUVdBWlVOQlYSDAgBEAEYASoCQUEyABgBIgQIARABKAIoAygEMAs) ## Popular airlines from Chicago to Harlingen, TX (HRL-Valley Intl.) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:HRL,departure:4/22/2026TANYT&leg2=from:HRL,to:CHI,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:HRL,departure:4/22/2026TANYT&leg2=from:HRL,to:CHI,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:HRL,departure:4/22/2026TANYT&leg2=from:HRL,to:CHI,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:HRL,departure:4/22/2026TANYT&leg2=from:HRL,to:CHI,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://a.travel-assets.com/air/airlines/sy_sq.svg) Sun Country Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:HRL,departure:4/22/2026TANYT&leg2=from:HRL,to:CHI,departure:4/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"SY"}}]) ## Cheap Flights from Chicago to Harlingen (CHI-HRL) Prices were available within the past 7 days and start at $138 for one-way flights and $275 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Oct 24 - Sat, Oct 31 ORD Chicago HRL Harlingen $275 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:10/24/2026TANYT&leg2=from:HRL,to:ORD,departure:10/31/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:274.40&airProductToken=AQpoCjIIwYIBEgQyNTMxGK4cIKOxASjCqJsDMOWpmwM4QkAAWAFqBUJBU0lDcghRV0FaVU5CVgoyCMGCARIEMzM0NBijsQEgp1wojKubAzDsq5sDOEJAAVgBagVCQVNJQ3IIUVdBWlVOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, Jun 9 - Tue, Jun 23 MDW Chicago HRL Harlingen $275 Roundtrip found 8 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:HRL,departure:6/9/2026TANYT&leg2=from:HRL,to:MDW,departure:6/23/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:274.40&airProductToken=AQpjCjAI15wBEgQyNzg1GOywASDHowEou6OPAzDWpI8DOFZAAFgBagNXR0FyB1ZEQVdXMkcKLwjXnAESBDQ3OTQYx6MBIKdcKI-mjwMw0KaPAzhWQAFYAWoDV0dBcgdWREFXVzJHEgwIARABGAEqAldOMgAYASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Fri, May 8 - Wed, May 13 ORD Chicago HRL Harlingen $276 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:5/8/2026TANYT&leg2=from:HRL,to:ORD,departure:5/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:275.40&airProductToken=AQpiCi8I15wBEgQzNzU2GK4cIICVASidu4wDMMy8jAM4VkAAWAFqA1dHQXIHVkxBVVcyRwovCNecARIEMTExOBiAlQEgp1wo-byMAzC_vYwDOFZAAVgBagNXR0FyB1ZMQVVXMkcSDAgBEAEYASoCV04yABgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Thu, Apr 30 - Wed, May 6 ORD Chicago HRL Harlingen $277 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:4/30/2026TANYT&leg2=from:HRL,to:ORD,departure:5/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:276.40&airProductToken=AQpiCi8I15wBEgQzNzU2GK4cIICVASid4YsDMMziiwM4VkAAWAFqA1dHQXIHVkxBVVcyRwovCNecARIEMTExOBiAlQEgp1wo-eKLAzC_44sDOFZAAVgBagNXR0FyB1ZMQVVXMkcSDAgBEAEYASoCV04yABgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, May 20 - Sat, May 30 ORD Chicago HRL Harlingen $280 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:5/20/2026TANYT&leg2=from:HRL,to:ORD,departure:5/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:279.70&airProductToken=AQqQAQouCNecARIEMzY4MhiuHCCDWCi3wI0DMM3BjQM4VkAAWAFqA1dHQXIHVkRBV1cyRwotCNecARICMzcYg1ggx6MBKI7CjQMw3sKNAzhWQAFYAWoDV0dBcgdWREFXVzJHCi8I15wBEgQyMzI1GMejASCnXCjOxI0DMJTFjQM4VkABWAFqA1dHQXIHVkRBV1cyRxIMCAEQARgBKgJXTjIAGAEiBAgBEAEoAigDKAQwAQ) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, May 5 - Tue, May 12 ORD Chicago HRL Harlingen $281 Roundtrip found 11 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:5/5/2026TANYT&leg2=from:HRL,to:ORD,departure:5/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:280.70&airProductToken=AQqQAQouCNecARIEMzY4MhiuHCCDWCjXl4wDMO2YjAM4VkAAWAFqA1dHQXIHVkxBVVcyRwotCNecARICMzcYg1ggx6MBKK6ZjAMw_pmMAzhWQAFYAWoDV0dBcgdWTEFVVzJHCi8I15wBEgQyMzI1GMejASCnXCjum4wDMLScjAM4VkABWAFqA1dHQXIHVkxBVVcyRxIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Thu, Apr 30 - Wed, May 6 ORD Chicago HRL Harlingen $282 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:4/30/2026TANYT&leg2=from:HRL,to:ORD,departure:5/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:281.70&airProductToken=AQqRAQotCNecARIDNjU4GK4cIKEDKNzgiwMwwOGLAzhWQABYAWoDV0dBcgdWTEFVVzJHCi8I15wBEgQyNjI1GKEDIMejASjC4osDMMnjiwM4VkABWAFqA1dHQXIHVkxBVVcyRwovCNecARIEMjMyNRjHowEgp1woj-SLAzDQ5IsDOFZAAVgBagNXR0FyB1ZMQVVXMkcSDAgBEAEYASoCV04yABgBIgQIARABKAIoAygEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Jun 10 - Tue, Jun 23 ORD Chicago HRL Harlingen $289 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:6/10/2026TANYT&leg2=from:HRL,to:ORD,departure:6/23/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:288.38&airProductToken=AQpwCjYI1YIBEgQxNzk5GK4cIIg4KJKqjwMwu6uPAzhOQABYAWoKMV9iYXNpY2Vjb3IIS0FLNVBGQk4KNgjVggESBDQyODcYiDggp1wo56yPAzC2rY8DOE5AAFgBagoxX2Jhc2ljZWNvcghLQUs1UEZCThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Apr 21 - Tue, Apr 28 ORD Chicago HRL Harlingen $291 Roundtrip found 13 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:4/21/2026TANYT&leg2=from:HRL,to:ORD,departure:4/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:290.79&airProductToken=AQpuCjUIxJgBEgQxNTc0GK4cIMx8KN74igMwwvmKAzhFQABYAWoJTUFJTkJBU0lDcghYQVVOQTBCQwo1CMSYARIEMTcwMRjMfCCnXCiN-ooDMNX7igM4RUABWAFqCU1BSU5CQVNJQ3IIWEFVTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Sun Country Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/SY.GIF) Thu, Apr 23 - Sun, Apr 26 ORD Chicago HRL Harlingen $503 Roundtrip found 12 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:4/23/2026TANYT&leg2=from:HRL,to:ORD,departure:4/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:502.76&airProductToken=AQpUCigI07IBEgMyNjIYrhwgzHwojZSLAzD3lIsDOFNAAFgBcgdTNERBQ0FZCigI07IBEgM2MjEYzHwgp1womJqLAzDXm4sDOFNAAVgBcgdTNERBQ0FZClQKKAjTsgESAzYyMhinXCDMfCj_sYsDMLqziwM4SUAAWAFyB0k3REFDQVkKKAjTsgESAzI2MRjMfCCuHCi4tIsDMJi1iwM4SUABWAFyB0k3REFDQVkSCggBEAEYASoCU1kYASIECAEQASgCKAMoBDAN) ## Alternative airports near Harlingen Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BRO,departure:4/22/2026TANYT&leg2=from:BRO,to:ORD,departure:4/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) BRO Brownsville-South Padre Island Intl. 33 min [Flights from $357 ](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BRO,departure:4/22/2026TANYT&leg2=from:BRO,to:ORD,departure:4/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Travel information | Origin airport | Midway Intl. | | ------------------- | -------------------------------------------------------------------------- | | Destination airport | Valley Intl. | | Airlines serving | American Airlines, Delta, Southwest Airlines, Sun Country Airlines, United | | Roundtrip price | $274 | | Distance | 1214 mi | \*Flight schedules are subject to change. \*Available to One Key members. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Iwo Jima Monument ](https://www.expedia.com/Iwo-Jima-Monument-Hotels.0-l6236802-0.Travel-Guide-Filter-Hotels) - [Hotels near Iwo Jima Memorial Museum ](https://www.expedia.com/Iwo-Jima-Memorial-Museum-Hotels.0-l553248621532643251-0.Travel-Guide-Filter-Hotels) - [Hotels near Rio Grande Valley Museum ](https://www.expedia.com/Rio-Grande-Valley-Museum-Hotels.0-l553248621532643250-0.Travel-Guide-Filter-Hotels) - [Hotels near Harlingen Soccer Complex ](https://www.expedia.com/Harlingen-Soccer-Complex-Hotels.0-l6236794-0.Travel-Guide-Filter-Hotels) - [Hotels near Harlingen Arts & Heritage Museum ](https://www.expedia.com/Harlingen-Arts-Heritage-Museum-Hotels.0-l553248621533114240-0.Travel-Guide-Filter-Hotels) - [Harlingen Hotels ](https://www.expedia.com/Harlingen-Hotels.d1515.Travel-Guide-Hotels) - [Flights to Harlingen ](https://www.expedia.com/Cheap-Flights-To-Harlingen.d1515.Travel-Guide-Flights) - [Minneapolis - St. Paul to Harlingen ](https://www.expedia.com/lp/flights/178287/1515/minneapolis-st-paul-to-harlingen) - [Fort Lauderdale to Harlingen ](https://www.expedia.com/lp/flights/601750/1515/fort-lauderdale-to-harlingen) - [Chicago to Harlingen ](https://www.expedia.com/lp/flights/178248/1515/chicago-to-harlingen) - [Iwo Jima Monument ](https://www.expedia.com/Iwo-Jima-Monument-Harlingen.d6236802.Vacation-Attraction) - [Iwo Jima Memorial Museum ](https://www.expedia.com/Iwo-Jima-Memorial-Museum-Harlingen.d553248621532643251.Vacation-Attraction) - [Rio Grande Valley Museum ](https://www.expedia.com/Rio-Grande-Valley-Museum-Harlingen.d553248621532643250.Vacation-Attraction) - [Harlingen Soccer Complex ](https://www.expedia.com/Harlingen-Soccer-Complex-Harlingen.d6236794.Vacation-Attraction) - [Car rentals near Iwo Jima Memorial Museum ](https://www.expedia.com/Car-Rentals-In-Iwo-Jima-Memorial-Museum.d553248621532643251.Car-Rental-Guide) - [Car rentals near Harlingen Soccer Complex ](https://www.expedia.com/Car-Rentals-In-Harlingen-Soccer-Complex.d6236794.Car-Rental-Guide) - [Car rentals near Harlingen ](https://www.expedia.com/Car-Rentals-In-Harlingen.d1515.Car-Rental-Guide)