Title: Chicago to Laredo cheap flights from $588 (MDW to LRD) - Expedia.com ![rio grande texas usa mexico border](https://images.trvl-media.com/place/2131/569066c0-e2ff-4abf-b7a2-f3e6fa240057.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/2131/569066c0-e2ff-4abf-b7a2-f3e6fa240057.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $588 Cheap Flights from Chicago (MDW) to Laredo (LRD) [View $588 flight on Fri, May 15, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MDW,to:LRD,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:587.50&airProductToken=AQqkAQo2CMSYARIEMTI4NRjssAEg4Fwoy4WNAzDGho0DOEtAAFgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjUIxJgBEgQxMTQ4GOBcIIg4KOCHjQMw5oiNAzhLQAFYAWoJTUFJTkNMQVNDcghLQVZPQTBNQwozCNWCARIENDM2NhiIOCCrHCjCiY0DMJ6KjQM4UUABWAFqB0VDT05PTVlyCFFBQTJPREVOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwAQ) ## Popular airlines from Chicago Midway Airport (MDW) to Laredo, TX (LRD-Laredo Intl.) - ![](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:MDW,to:LRD,departure:4/11/2026TANYT&leg2=from:LRD,to:MDW,departure:4/18/2026TANYT&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:MDW,to:LRD,departure:4/11/2026TANYT&leg2=from:LRD,to:MDW,departure:4/18/2026TANYT&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_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:LRD,departure:4/11/2026TANYT&leg2=from:LRD,to:MDW,departure:4/18/2026TANYT&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_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:LRD,departure:4/11/2026TANYT&leg2=from:LRD,to:MDW,departure:4/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:LRD,departure:4/11/2026TANYT&leg2=from:LRD,to:MDW,departure:4/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:LRD,departure:4/11/2026TANYT&leg2=from:LRD,to:MDW,departure:4/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:LRD,departure:4/11/2026TANYT&leg2=from:LRD,to:MDW,departure:4/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheap Flights from Chicago to Laredo (MDW-LRD) Prices were available within the past 7 days and start at $588 for one-way flights and $1,175 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) Wed, Nov 4 - Thu, Nov 12 MDW Chicago LRD Laredo $1,175 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:11/4/2026TANYT&leg2=from:LRD,to:MDW,departure:11/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1175.00&airProductToken=AQqkAQo2CMSYARIEMTI4NRjssAEg4FwokKCcAzCIoZwDOEtAAFgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjUIxJgBEgQxNjgyGOBcIIg4KLWhnAMwwqKcAzhLQAFYAWoJTUFJTkNMQVNDcghLQVZPQTBNQwozCNWCARIENDkzNhiIOCCrHCj0pZwDML-mnAM4UUABWAFqB0VDT05PTVlyCFFBQTJPREVOCqYBCjMI1YIBEgQ0MjI2GKscIIg4KMz6nAMwnvucAzhRQABYAWoHRUNPTk9NWXIIUUFBMk9ERU4KNgjEmAESBDE2MzIYiDgg47QBKNr8nAMwg_6cAzhLQAFYAWoJTUFJTkNMQVNDcghLQVZPQTBNQwo3CMSYARIENDY3NxjjtAEg7LABKLP_nAMwhYCdAzhLQAFYAWoJTUFJTkNMQVNDcghLQVZPQTBNQxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 4 - Thu, Nov 12 MDW Chicago LRD Laredo $1,185 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:11/4/2026TANYT&leg2=from:LRD,to:MDW,departure:11/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1185.00&airProductToken=AQqmAQo3CMSYARIENDY4NBjssAEg47QBKOKhnAMwqaKcAzhLQABYAWoJTUFJTkNMQVNDcghLQVZPQTBNQwo2CMSYARIEMTMwNxjjtAEgiDgo2qKcAzCcpJwDOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjMI1YIBEgQ0ODkyGIg4IKscKNCnnAMwnaicAzhRQAFYAWoHRUNPTk9NWXIIUUFBMk9ERU4KpgEKMwjVggESBDQyMjYYqxwgiDgozPqcAzCe-5wDOEhAAFgBagdFQ09OT01ZcghIQUE0QURFTgo2CMSYARIEMTYzMhiIOCDjtAEo2vycAzCD_pwDOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjcIxJgBEgQ0Njc3GOO0ASDssAEos_-cAzCFgJ0DOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, May 14 - Mon, May 18 MDW Chicago LRD Laredo $1,195 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:5/14/2026TANYT&leg2=from:LRD,to:MDW,departure:5/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1195.00&airProductToken=AQqkAQo2CMSYARIEMTI4NRjssAEg4Fwoq_qMAzCm-4wDOEtAAFgBaglNQUlOQ0xBU0NyCEtBV09BME1DCjUIxJgBEgQxMTQ4GOBcIIg4KMD8jAMwxv2MAzhLQAFYAWoJTUFJTkNMQVNDcghLQVdPQTBNQwozCNWCARIENDkzNhiIOCCrHCiHgI0DMOOAjQM4UUABWAFqB0VDT05PTVlyCFFBQTJPREVOCqQBCjMI1YIBEgQ0Mjk3GKscIIg4KImqjQMw4KqNAzhRQABYAWoHRUNPTk9NWXIIUUFBMk9ERU4KNQjEmAESBDExNDgYiDgg4FwoiKuNAzCHrI0DOEtAAVgBaglNQUlOQ0xBU0NyCEtBV09BME1RCjYIxJgBEgQxMDc2GOBcIOywASiqrY0DMKGujQM4S0ABWAFqCU1BSU5DTEFTQ3IIS0FXT0EwTVESCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Jun 19 - Tue, Jun 23 MDW Chicago LRD Laredo $1,225 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:6/19/2026TANYT&leg2=from:LRD,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:1225.00&airProductToken=AQqmAQo3CMSYARIENDY3NBjssAEg47QBKNmQkAMwp5GQAzhLQABYAWoJTUFJTkNMQVNDcghLQVZPQTBNQwo2CMSYARIEMTMwNxjjtAEgiDgo2ZGQAzCNk5ADOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjMI1YIBEgQ0Mjg1GIg4IKscKJaVkAMw6pWQAzhRQAFYAWoHRUNPTk9NWXIIUUFBMk9ERU4KpgEKMwjVggESBDQzNTcYqxwgiDgo5r2QAzC9vpADOFFAAFgBagdFQ09OT01ZcghRQUEyT0RFTgo2CMSYARIEMTA0MxiIOCDjtAEo4L6QAzCIwJADOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjcIxJgBEgQ0Njc3GOO0ASDssAEor8GQAzCDwpADOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Jun 19 - Tue, Jun 23 MDW Chicago LRD Laredo $1,235 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:6/19/2026TANYT&leg2=from:LRD,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:1235.00&airProductToken=AQqkAQo2CMSYARIENTQ2ORjssAEgzHwo_pCQAzDjkZADOEtAAFgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjUIxJgBEgQyNjQ0GMx8IIg4KKGTkAMw05SQAzhLQAFYAWoJTUFJTkNMQVNDcghLQVZPQTBNQwozCNWCARIENDI4NRiIOCCrHCiWlZADMOqVkAM4SEABWAFqB0VDT05PTVlyCEhBQTRBREVOCqYBCjMI1YIBEgQ0MzU3GKscIIg4KOa9kAMwvb6QAzhRQABYAWoHRUNPTk9NWXIIUUFBMk9ERU4KNgjEmAESBDEwNDMYiDgg47QBKOC-kAMwiMCQAzhLQAFYAWoJTUFJTkNMQVNDcghLQVZPQTBNQwo3CMSYARIENDY3NxjjtAEg7LABKK_BkAMwg8KQAzhLQAFYAWoJTUFJTkNMQVNDcghLQVZPQTBNQxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 4 - Thu, Nov 12 MDW Chicago LRD Laredo $1,265 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:11/4/2026TANYT&leg2=from:LRD,to:MDW,departure:11/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1265.00&airProductToken=AQqkAQo2CMSYARIEMTA2MxjssAEg4Fwoo6KcAzCYo5wDOEtAAFgBaglNQUlOQ0xBU0NyCEtBV09BME1RCjUIxJgBEgQxMjIzGOBcIIg4KP-jnAMwi6WcAzhLQAFYAWoJTUFJTkNMQVNDcghLQVdPQTBNUQozCNWCARIENDkzNhiIOCCrHCj0pZwDML-mnAM4UUABWAFqB0VDT05PTVlyCFFBQTJPREVOCqQBCjMI1YIBEgQ0MjI2GKscIIg4KMz6nAMwnvucAzhVQABYAWoHRUNPTk9NWXIIVUFBN0FERU4KNQjEmAESBDI2NTYYiDggzHworfycAzDW_ZwDOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjYIxJgBEgQ0NzE0GMx8IOywASiG_5wDMOr_nAM4S0ABWAFqCU1BSU5DTEFTQ3IIS0FWT0EwTUMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Jun 18 - Mon, Jun 22 MDW Chicago LRD Laredo $1,275 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:6/18/2026TANYT&leg2=from:LRD,to:MDW,departure:6/22/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1275.00&airProductToken=AQqmAQo3CMSYARIENDY4OBjssAEg47QBKKiHkAMw9oeQAzhLQABYAWoJTUFJTkNMQVNDcghLQVZPQTBNQwo2CMSYARIEMTUyORjjtAEgiDgon4iQAzDYiZADOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjMI1YIBEgQ0ODkyGIg4IKscKKGLkAMw74uQAzhRQAFYAWoHRUNPTk9NWXIIUUFBMk9ERU4KpgEKMwjVggESBDQyMjYYqxwgiDgov7GQAzCWspADOFFAAFgBagdFQ09OT01ZcghRQUEyT0RFTgo2CMSYARIEMTA0MxiIOCDjtAEowLOQAzDotJADOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DCjcIxJgBEgQ0Njc3GOO0ASDssAEoj7aQAzDjtpADOEtAAVgBaglNQUlOQ0xBU0NyCEtBVk9BME1DEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 4 - Thu, Nov 12 MDW Chicago LRD Laredo $1,286 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:11/4/2026TANYT&leg2=from:LRD,to:MDW,departure:11/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1285.01&airProductToken=AQqmAQo3CMSYARIENDY4OBjssAEg47QBKLSjnAMw-qOcAzhLQABYAWoJTUFJTkNMQVNDcghLQVdPQTBNQwo2CMSYARIEMTcxOBjjtAEgiDgou6ScAzD8pZwDOEtAAVgBaglNQUlOQ0xBU0NyCEtBV09BME1DCjMI1YIBEgQ0ODkyGIg4IKscKNCnnAMwnaicAzhRQAFYAWoHRUNPTk9NWXIIUUFBMk9ERU4KpAEKMwjVggESBDQyMjYYqxwgiDgozPqcAzCe-5wDOEhAAFgBagdFQ09OT01ZcghIQUE0QURFTgo1CMSYARIEMTU4NRiIOCDgXCjs-5wDMOj8nAM4UUABWAFqCU1BSU5DTEFTQ3IIUUFVT0EwTUMKNgjEmAESBDE3MjgY4Fwg7LABKI7-nAMwgf-cAzhRQAFYAWoJTUFJTkNMQVNDcghRQVVPQTBNQxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Apr 9 - Sun, Apr 12 MDW Chicago LRD Laredo $1,287 Roundtrip found 13 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:4/9/2026TANYT&leg2=from:LRD,to:MDW,departure:4/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1286.02&airProductToken=AQqkAQo2CMSYARIEMjQxNxjssAEg4Fwoy_OJAzC-9IkDOEtAAFgBaglNQUlOQ0xBU0NyCEtBME9BME1DCjUIxJgBEgQxMTMxGOBcIIg4KO70iQMw-fWJAzhLQAFYAWoJTUFJTkNMQVNDcghLQTBPQTBNQwozCNWCARIENDkzNhiIOCCrHCjy9okDMM73iQM4UUABWAFqB0VDT05PTVlyCFFGQTBPREROCqYBCjMI1YIBEgQ0MjI2GKscIIg4KN-SigMwtpOKAzhIQABYAWoHRUNPTk9NWXIISEFBNEFERU4KNgjEmAESBDE2OTkYiDgg47QBKOeUigMwiJaKAzhLQAFYAWoJTUFJTkNMQVNDcghLQVVPQTBNQwo3CMSYARIENTI3NRjjtAEg7LABKJSXigMw3peKAzhLQAFYAWoJTUFJTkNMQVNDcghLQVVPQTBNQxIMCAEQARgBKgJVQTIAGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Apr 12 - Mon, Apr 13 MDW Chicago LRD Laredo $1,296 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:LRD,departure:4/12/2026TANYT&leg2=from:LRD,to:MDW,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1295.01&airProductToken=AQqkAQo2CMSYARIEMTI4NRjssAEg4FwolJKKAzCMk4oDOEtAAFgBaglNQUlOQ0xBU0NyCEtBVU9BME1DCjUIxJgBEgQxNjgyGOBcIIg4KMOTigMw0ZSKAzhLQAFYAWoJTUFJTkNMQVNDcghLQVVPQTBNQwozCNWCARIENDkwNBiIOCCrHCi3lYoDMJKWigM4VUABWAFqB0VDT05PTVlyCFVBQTdBREVOCqYBCjMI1YIBEgQ0MjI2GKscIIg4KP-digMw1p6KAzhIQABYAWoHRUNPTk9NWXIISEFBNEFERU4KNgjEmAESBDE2MzIYiDgg47QBKISgigMwqKGKAzhLQAFYAWoJTUFJTkNMQVNDcghLQVVPQTBNQwo3CMSYARIENTI3NBjjtAEg7LABKLSiigMwgqOKAzhLQAFYAWoJTUFJTkNMQVNDcghLQVVPQTBNQxIMCAEQARgBKgJVQTIAGAEiBAgBEAEoAigDKAQwAQ) ## Frequently asked questions ### How much does a flight from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.) cost? ### What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ### Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ### What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ### How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ### What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ### What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ### How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ### Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ### How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.) flight with Expedia? ### Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.) at the last minute? ### Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.) flight and hotel package? ### Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Laredo, TX (LRD-Laredo Intl.)? ## Travel information | Origin airport | Midway Intl. | | ------------------- | ------------ | | Destination airport | Laredo Intl. | | Roundtrip price | $1,175 | | Distance | 1185 mi | ## Book with confidence # Chicago to Laredo Flights The cheapest times to fly from Chicago to Laredo 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 Laredo are during the month of November. You can find some of the cheapest flights from Chicago to Laredo with Expedia's search tool and vast selection of airlines. The best time to book a flight from Chicago to Laredo Sunday is one of the best days to book for cheap flights from Chicago to Laredo: 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 Laredo 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 Laredo in 2026\. You can also book with separate airlines for your outbound and return journeys, from $588 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 Laredo 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 Laredo 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\. The percentages you see are averages. \*Flight schedules are subject to change. \*Available to One Key members. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Laredo Hotels ](https://www.expedia.com/Laredo-Hotels.d2131.Travel-Guide-Hotels) - [Hotels near Uni-Trade Stadium ](https://www.expedia.com/Uni-Trade-Stadium-Hotels.0-l553248621587242538-0.Travel-Guide-Filter-Hotels) - [Hotels near Laredo Little Theatre ](https://www.expedia.com/Laredo-Little-Theatre-Hotels.0-l553248621561865542-0.Travel-Guide-Filter-Hotels) - [Hotels near Sames Auto Arena ](https://www.expedia.com/Sames-Auto-Arena-Hotels.0-l6164225-0.Travel-Guide-Filter-Hotels) - [Hotels near Arena Gun Club ](https://www.expedia.com/Arena-Gun-Club-Hotels.0-l553248621587242539-0.Travel-Guide-Filter-Hotels) - [Hotels near San Agustín Church ](https://www.expedia.com/San-Agustin-Church-Hotels.0-l553248621533114223-0.Travel-Guide-Filter-Hotels) - [Flights to Laredo ](https://www.expedia.com/Cheap-Flights-To-Laredo.d2131.Travel-Guide-Flights) - [Los Angeles to Laredo ](https://www.expedia.com/lp/flights/178280/2131/los-angeles-to-laredo) - [Uni-Trade Stadium ](https://www.expedia.com/Uni-Trade-Stadium-Laredo.d553248621587242538.Vacation-Attraction) - [Sames Auto Arena ](https://www.expedia.com/Sames-Auto-Arena-Laredo.d6164225.Vacation-Attraction) - [Arena Gun Club ](https://www.expedia.com/Arena-Gun-Club-Laredo.d553248621587242539.Vacation-Attraction) - [San Agustín Church ](https://www.expedia.com/San-Agustin-Church-Laredo.d553248621533114223.Vacation-Attraction) - [Car rentals near Laredo ](https://www.expedia.com/Car-Rentals-In-Laredo.d2131.Car-Rental-Guide)