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 Sat, May 30, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:ORD,to:HRL,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:137.20&airProductToken=AQpoCjIIwYIBEgQzMDUyGK4cIKOxASjwr44DMI2xjgM4QkAAWAFqBUJBU0lDcghRV0FaVU5CVgoyCMGCARIEMzU3NRijsQEgp1wowbKOAzCcs44DOEJAAVgBagVCQVNJQ3IIUVdBWlVOQlYSDAgBEAEYASoCQUEyABgBIgQIARABKAIoAygEMAs) ## 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:4/17/2026TANYT&leg2=from:HRL,to:CHI,departure:4/24/2026TANYT&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_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:HRL,departure:4/17/2026TANYT&leg2=from:HRL,to:CHI,departure:4/24/2026TANYT&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_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:HRL,departure:4/17/2026TANYT&leg2=from:HRL,to:CHI,departure:4/24/2026TANYT&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_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:HRL,departure:4/17/2026TANYT&leg2=from:HRL,to:CHI,departure:4/24/2026TANYT&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:4/17/2026TANYT&leg2=from:HRL,to:CHI,departure:4/24/2026TANYT&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 ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Oct 24 - Sat, Oct 31 ORD Chicago HRL Harlingen $275 Roundtrip found 4 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=AQpuCjUIxJgBEgQxNzE3GK4cIMx8KPSjmwMw1KSbAzhFQABYAWoJTUFJTkJBU0lDcghYQVdOSDNCQwo1CMSYARIEMjExNBjMfCCnXCigppsDMOmnmwM4RUABWAFqCU1BSU5CQVNJQ3IIWEFXTkgzQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, May 23 - Sat, Jun 13 ORD Chicago HRL Harlingen $275 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:5/23/2026TANYT&leg2=from:HRL,to:ORD,departure:6/13/2026TANYT&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=AQpwCjYI1YIBEgQxNzk5GK4cIIg4KNLfjQMw--CNAzhOQABYAWoKMV9iYXNpY2Vjb3IIS0FLNVBGQk4KNgjVggESBDQyODcYiDggp1wop-KNAzD24o0DOE5AAFgBagoxX2Jhc2ljZWNvcghLQUs1UEZCThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, May 26 - Tue, Jun 16 MDW Chicago HRL Harlingen $275 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:HRL,departure:5/26/2026TANYT&leg2=from:HRL,to:MDW,departure:6/16/2026TANYT&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=AQphCi8I15wBEgM2NjcY7LABIICVASiAgY4DMKCCjgM4VkAAWAFqA1dHQXIHVkRBV1cyRwouCNecARIDMzU5GICVASCnXCjIgo4DMImDjgM4VkABWAFqA1dHQXIHVkRBV1cyRxIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE) ![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 just found [](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) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, Apr 26 - Tue, Apr 28 ORD Chicago HRL Harlingen $277 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:4/26/2026TANYT&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:276.40&airProductToken=AQpnCjEIwYIBEgMzNTcYrhwgo7EBKJiviwMwt7CLAzhCQABYAWoFQkFTSUNyCFFVQVpaTkJWCjIIwYIBEgQzNjUyGKOxASCnXCjxsIsDMNWxiwM4QkABWAFqBUJBU0lDcghRVUFaWk5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Apr 13 - Mon, Apr 20 ORD Chicago HRL Harlingen $278 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:4/13/2026TANYT&leg2=from:HRL,to:ORD,departure:4/20/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:277.46&airProductToken=AQpvCjUI1YIBEgM3MTQYrhwgiDgoj6KKAzDJo4oDOE5AAFgBagoxX2Jhc2ljZWNvcghLQUE0UEZCTgo2CNWCARIENDkxORiIOCCnXCifpIoDMPOkigM4TkAAWAFqCjFfYmFzaWNlY29yCEtBQTRQRkJOCnAKNgjVggESBDQ4NzAYp1wgiDgouvGKAzCN8ooDOE5AAFgBagoxX2Jhc2ljZWNvcghLQUE0UEZCTgo2CNWCARIEMTc1MhiIOCCuHCj28ooDMJ_0igM4TkAAWAFqCjFfYmFzaWNlY29yCEtBQTRQRkJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, May 2 - Sat, May 9 ORD Chicago HRL Harlingen $280 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:5/2/2026TANYT&leg2=from:HRL,to:ORD,departure:5/9/2026TANYT&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=AQpoCjIIwYIBEgQxOTM4GK4cIKOxASjr9YsDMIr3iwM4QkAAWAFqBUJBU0lDcghRV0FaVU5CVgoyCMGCARIEMzU3NRijsQEgp1wo4PiLAzDB-YsDOEJAAVgBagVCQVNJQ3IIUVdBWlVOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Apr 12 - Tue, Apr 14 ORD Chicago HRL Harlingen $281 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:4/12/2026TANYT&leg2=from:HRL,to:ORD,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:280.60&airProductToken=AQpuCjUIxJgBEgQxNjEzGK4cIMx8KMOTigMwopSKAzhFQABYAWoJTUFJTkJBU0lDcghYQVVOQTBCQwo1CMSYARIEMTcwMRjMfCCnXCj0lIoDMLmWigM4RUABWAFqCU1BSU5CQVNJQ3IIWEFVTkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Apr 22 - Sun, Apr 26 MDW Chicago HRL Harlingen $282 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:HRL,departure:4/22/2026TANYT&leg2=from:HRL,to:MDW,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:281.70&airProductToken=AQpvCjYIxJgBEgQzNzc4GOywASDMfCilhIsDMIqFiwM4RUAAWAFqCU1BSU5CQVNJQ3IIWEFVTkEwQkMKNQjEmAESBDE3MDEYzHwgp1worYWLAzD1hosDOEVAAVgBaglNQUlOQkFTSUNyCFhBVU5BMEJDEgwIARABGAEqAkRMMgAYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Apr 23 - Sat, Apr 25 ORD Chicago HRL Harlingen $284 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:HRL,departure:4/23/2026TANYT&leg2=from:HRL,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:283.40&airProductToken=AQpnCjEIwYIBEgMzNTcYrhwgo7EBKLiNiwMw146LAzhCQABYAWoFQkFTSUNyCFFVQVpaTkJWCjIIwYIBEgQzNjUyGKOxASCnXCiRj4sDMPWPiwM4QkABWAFqBUJBU0lDcghRVUFaWk5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ## 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:4/17/2026TANYT&leg2=from:BRO,to:ORD,departure:4/19/2026TANYT&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 $367 ](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BRO,departure:4/17/2026TANYT&leg2=from:BRO,to:ORD,departure:4/19/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Chicago (CHI) to Harlingen (HRL) ### October is typically the cheapest month to fly From $175 - $438 per traveler. ## 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 | ## Book with confidence # Chicago to Harlingen Flights The cheapest times to fly from Chicago to Harlingen On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Harlingen are during the month of October. You can find some of the cheapest flights from Chicago to Harlingen with Expedia's search tool and vast selection of airlines. The best time to book a flight from Chicago to Harlingen Sunday is one of the best days to book for cheap flights from Chicago to Harlingen: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance. How to find cheap round-trip tickets from Chicago to Harlingen Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Harlingen in 2026\. You can also book with separate airlines for your outbound and return journeys, from $138 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members. Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Harlingen flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps. You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Chicago to Harlingen airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures. \*Terms apply. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. 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