
Popular airlines from Luis Munoz Marin Intl. Airport (SJU) to Chicago O'Hare Intl. Airport (ORD)
- Spirit Airlines
Spirit Airlines
- United
United
- JetBlue Airways
JetBlue Airways
- American Airlines
American Airlines
- Delta
Delta
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier Airlines
- Plan, book, fly with confidence
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Cheap Flights from San Juan to Chicago (SJU-ORD)
Prices were available within the past 7 days and start at $94 for one-way flights and $189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.










Find the cheapest month to fly from San Juan (SJU) to Chicago (ORD)
January is typically the cheapest month to fly
Graph displaying average flight prices per month
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
Origin airport | Luis Munoz Marin Intl. |
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, United |
Roundtrip price | $189 |
Distance | 2073 mi |
Average flight time | 4 hours 15 mins |
San Juan to Chicago Flights
The cheapest times to fly from San Juan to Chicago
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 San Juan to Chicago are during the month of August. You can find some of the cheapest flights from San Juan to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from San Juan to Chicago
Sunday is one of the best days to book for cheap flights from San Juan to Chicago: 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 San Juan to Chicago
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 San Juan to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $94 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 San Juan to Chicago 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. Bundling together your San Juan to Chicago 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.
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Top Routes from San Juan
- San Juan to Newark Liberty Intl. Airport (SJU - EWR)
- San Juan to Santo Domingo (SJU - SDQ)
- San Juan to Punta Cana (SJU - PUJ)
- San Juan to Miami (SJU - MIA)
- San Juan to Tampa (SJU - TPA)
- San Juan to Fort Lauderdale (SJU - FLL)
- San Juan to New York (SJU - LGA)
- San Juan to Boston (SJU - BOS)
- San Juan to Hartford (SJU - BDL)
- San Juan to New York (SJU - JFK)
- San Juan to Medellín (SJU - MDE)
- San Juan to Trenton (SJU - TTN)
Top Routes to Chicago
- Newark Liberty Intl. Airport to Chicago (EWR - ORD)
- Phoenix to Chicago (PHX - ORD)
- Los Angeles to Chicago (LAX - ORD)
- Tampa to Chicago (TPA - ORD)
- Miami to Chicago (MIA - ORD)
- New York to Chicago (LGA - ORD)
- Boston to Chicago (BOS - ORD)
- Fort Lauderdale to Chicago (FLL - ORD)
- Orange County to Chicago (SNA - ORD)
- Denver to Chicago (DEN - ORD)
- New York to Chicago (JFK - ORD)
- Dallas to Chicago (DAL - ORD)
Top Routes from San Juan
- JetBlue Airways San Juan to Newark Liberty Intl. Airport
- JetBlue Airways San Juan to Santo Domingo
- JetBlue Airways San Juan to Punta Cana
- American Airlines San Juan to Miami
- JetBlue Airways San Juan to Tampa
- JetBlue Airways San Juan to Fort Lauderdale
- Spirit Airlines San Juan to New York
- JetBlue Airways San Juan to Boston
- JetBlue Airways San Juan to Hartford
- JetBlue Airways San Juan to New York
Top Routes to Chicago
- Frontier Airlines Phoenix to Chicago
- Spirit Airlines Los Angeles to Chicago
- Spirit Airlines Tampa to Chicago
- Spirit Airlines New York to Chicago
- JetBlue Airways Boston to Chicago
- Spirit Airlines Fort Lauderdale to Chicago
- Alaska Airlines Orange County to Chicago
- Frontier Airlines Denver to Chicago
- JetBlue Airways New York to Chicago
- Alaska Airlines Seattle to Chicago
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Chicago
Ponce
Expedia's Latest Trends
- Chicago (ORD) to Dallas (DFW) Flights
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