Title: CA $153 Cheap Flights from Chicago (CHI) to San Juan (SJU) - Expedia.ca ![Condado Beach which includes general coastal views and a coastal town](https://images.trvl-media.com/place/6082351/ae98bc8e-4169-4654-a33a-bab2e7b17b7e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $153 Cheap Flights from Chicago (CHI) to San Juan (SJU) [View CA $153 flight on Mon, Nov 10, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:ORD,to:SJU,departure:10/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:152.05&airProductToken=AQovCi0IzpYBEgQzMDMxGK4cILKiASio2vwCMLzc_AI4R0AAWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Chicago to San Juan (SJU-Luis Munoz Marin Intl.) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:sju,departure:23/10/2025TANYT&leg2=from:sju,to:chi,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:sju,departure:23/10/2025TANYT&leg2=from:sju,to:chi,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:sju,departure:23/10/2025TANYT&leg2=from:sju,to:chi,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:sju,departure:23/10/2025TANYT&leg2=from:sju,to:chi,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:sju,departure:23/10/2025TANYT&leg2=from:sju,to:chi,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:sju,departure:23/10/2025TANYT&leg2=from:sju,to:chi,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:chi,to:sju,departure:23/10/2025TANYT&leg2=from:sju,to:chi,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) ![notification illustration](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\* ![deals illustration](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\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Chicago (CHI) to San Juan (SJU) Prices were available within the past 7 days and start at CA $153 for one-way flights and CA $305 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Mon, Nov 10 - Fri, Nov 14 ORD Chicago SJU San Juan CA $305 Roundtrip found 10 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:10/11/2025TANYT&leg2=from:SJU,to:ORD,departure:14/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:304.10&airProductToken=AQovCi0IzpYBEgQzMDMxGK4cILKiASio2vwCMLzc_AI4R0AAWAFqAlJQcgZHQTIxTlIKLwotCM6WARIEMzAzMhiyogEgrhwo_Yn9AjCzjP0COEdAAFgBagJSUHIGR0EyMU5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Oct 25 - Mon, Nov 3 ORD Chicago SJU San Juan CA $325 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:25/10/2025TANYT&leg2=from:SJU,to:ORD,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:324.87&airProductToken=AQouCiwIzpYBEgQyMDgwGK4cILKiASiQqfsCMKir-wI4VUAAWAFqAlNEcgVVQTdOUgovCi0IzpYBEgQzMDMyGLKiASCuHCidjvwCMNOQ_AI4R0AAWAFqAlJQcgZHQTIxTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Oct 25 - Mon, Nov 3 ORD Chicago SJU San Juan CA $337 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:25/10/2025TANYT&leg2=from:SJU,to:ORD,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:336.34&airProductToken=AQpeCiwIwmwSAzQwNhiuHCCpUSiOpvsCMKGn-wI4TEAAWAFqAkROcghQSTdRQkVMMQouCMJsEgQyOTAzGKlRILKiASjlqfsCMNSr-wI4TEABWAFqAkROcghQSTRRQkVMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Mon, Nov 10 - Thu, Nov 13 ORD Chicago SJU San Juan CA $350 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:10/11/2025TANYT&leg2=from:SJU,to:ORD,departure:13/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:349.25&airProductToken=AQovCi0IzpYBEgQzMDMxGK4cILKiASio2vwCMLzc_AI4R0AAWAFqAlJQcgZHQTIxTlIKWgosCM6WARIDMzQyGLKiASDlWijZ_vwCMIKA_QI4R0AAWAFqAlJQcgZHQTIxTlIKKgjOlgESAjE5GOVaIK4cKJuC_QIw44P9AjhHQAFYAWoCUlByBkdBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Oct 24 - Tue, Oct 28 ORD Chicago SJU San Juan CA $358 Roundtrip found 10 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:24/10/2025TANYT&leg2=from:SJU,to:ORD,departure:28/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:357.56&airProductToken=AQouCiwIzpYBEgQyMDgwGK4cILKiASjeoPsCMPui-wI4VUAAWAFqAlNEcgVVQTdOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Oct 25 - Mon, Nov 3 ORD Chicago SJU San Juan CA $359 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:25/10/2025TANYT&leg2=from:SJU,to:ORD,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:358.60&airProductToken=AQouCiwIzpYBEgQyMDgwGK4cILKiASiQqfsCMKir-wI4VUAAWAFqAlNEcgVVQTdOUgpeCi0IzpYBEgM1NzEYsqIBIKOxASjCkPwCMPyS_AI4V0AAWAFqAlJQcgZXQTIxTzEKLQjOlgESBDMwMzAYo7EBIK4cKP2X_AIwjZn8AjhXQAFYAWoCUlByBldBMjFPMRIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Oct 21 - Tue, Oct 28 ORD Chicago SJU San Juan CA $363 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:21/10/2025TANYT&leg2=from:SJU,to:ORD,departure:28/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:362.80&airProductToken=AQpdCiwIwmwSAzQwNhiuHCCpUSih-PoCMKf5-gI4TEAAWAFqAkROcghQSTRRUlNMMQotCMJsEgM4MDMYqVEgsqIBKM36-gIwuvz6AjhMQAFYAWoCRE5yCFBJNFFCRUwxCl8KLgjCbBIEMTEwNBiyogEgqVEo4sj7AjDTyvsCOExAAFgBagJETnIIUEk0UUJFTDEKLQjCbBIEMjEwNRipUSCuHCikzPsCMNDN-wI4TEABWAFqAkROcghQSTRRUlNMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Nov 10 - Fri, Nov 14 ORD Chicago SJU San Juan CA $407 Roundtrip found 10 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:10/11/2025TANYT&leg2=from:SJU,to:ORD,departure:14/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:406.45&airProductToken=AQppCjIIwYIBEgQxNjA2GK4cIOKaASi92_wCMLXc_AI4QkAAWAFqBUJBU0lDcghPTlgyQVRCWgozCMGCARIEMjA5OBjimgEgsqIBKNnd_AIwsN_8AjhCQAFYAWoFQkFTSUNyCE9OWDJBVEJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 12 - Thu, Jan 22 ORD Chicago SJU San Juan CA $438 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:12/01/2026TANYT&leg2=from:SJU,to:ORD,departure:22/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:437.80&airProductToken=AQpFCiAIxJgBEgQzODYzGK4cIKlRKOqeggMw_J-CAzhFQABYAQohCMSYARIEMTk2MRipUSCyogEovKCCAzCjooIDOEVAAVgBCkcKIgjEmAESBDE5MTMYsqIBIOO0ASiJkoMDMLqUgwM4RUAAWAEKIQjEmAESBDE2NjUY47QBIK4cKOaUgwMwvpWDAzhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, Jan 1 - Tue, Jan 13 ORD Chicago SJU San Juan CA $585 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:SJU,departure:01/01/2026TANYT&leg2=from:SJU,to:ORD,departure:13/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:584.80&airProductToken=AQpECiAI1YIBEgQyNjM4GK4cIIg4KMOkgQMw_KWBAzhMQABYAQogCNWCARIDNzAxGIg4ILKiASjQpoEDMNaogQM4TEABWAEKRQohCNWCARIEMjAyNBiyogEgiBgo_q2CAzDzr4IDOEtAAFgBCiAI1YIBEgQxNzM4GIgYIK4cKNCwggMw07GCAzhLQAFYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ## Find the cheapest month to fly from Chicago (CHI) to San Juan (SJU) ### January is typically the cheapest month to fly From CA $175 - CA $521 per traveller. ## Alternative airports near San Juan Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:ORD,to:SJU,departure:23/10/2025TANYT&leg2=from:SJU,to:ORD,departure:27/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) SJU Luis Munoz Marin Intl. Cheapest 16 min [Flights from CA $734](https://www.expedia.ca/Flights-Search?leg1=from:ORD,to:SJU,departure:23/10/2025TANYT&leg2=from:SJU,to:ORD,departure:27/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Travel information | Origin airport | O'Hare Intl. | | --- | --- | | Destination airport | Luis Munoz Marin Intl. | | Airlines serving | American Airlines, Delta, JetBlue Airways, Spirit Airlines, United | | Roundtrip price | CA $304 | | Distance | 3317 km | ## Book with confidence ### Illinois to San Juan Flights **The easy way to book your flights from Chicago to San Juan**  With Expedia, it’s simple to find and book flights to San Juan from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Luis Munoz Marin Intl., too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to San Juan today, tomorrow, or this week.   **Save dollars with cheap flights from CHI-All Airports, CHI to Luis Munoz Marin Intl., SJU**  Sort your search results by price to find great deals on your flight from Chicago to San Juan—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to San Juan from Chicago currently is just CA $305 rising to CA $585.   Here are more money-saving tips:  - Fly in November when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to San Juan   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to San Juan from Chicago**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to San Juan with Expedia today. \*Available to Expedia members.