On this page, you can find and book flights from San Juan to Chicago. Covering a distance of 3,309 km, this is a popular route with approximately 23 flights per week.
The route is served by United Airlines, American Airlines, and Spirit Airlines. Ticket prices are dynamic, so we recommend using the low-fare calendar and checking information on how to get to San Juan Airport and from Chicago airports.
The table shows direct flights San Juan → Chicago on the selected date. The flight takes approximately 5 h 5 min. Regular flights are operated by United Airlines, Spirit Airlines, American Airlines and Frontier Airlines. Departures from Luis Muñoz Marín International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.
For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.
Below is a calendar of the lowest flight ticket prices for San Juan — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 516 in ,, and the most expensive are around AED 957 in n. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.
San Juan → Chicago, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | AED 816 | high | May | AED 631 | low | Sep | AED 594 | low |
| Feb | AED 816 | high | Jun | AED 816 | high | Oct | AED 612 | low |
| Mar | AED 854 | high | Jul | AED 854 | high | Nov | AED 705 | medium |
| Apr | AED 668 | medium | Aug | AED 742 | medium | Dec | AED 928 | high |
Some values are estimated based on seasonality.
Chicago's climate is distinctly seasonal: the warmest period is July and August, with an average high of 26.5°C. January is considered the coldest month, when temperatures drop to -5°C, while rainfall peaks in May.
The lowest flight prices are recorded in August and September — from AED 516. The most expensive month to fly this route is March, when the cost reaches AED 957.
September is the most balanced month for a trip, offering a comfortable 23.5°C along with the lowest ticket prices. Conversely, it is better to avoid March dates due to peak travel costs.
There are 5 airlines operating on this route, with United Airlines and American Airlines accounting for the majority of the flights. Passengers can choose from both direct flights and connecting options, with a total frequency of about 23 departures per week. You can find a detailed schedule for specific days in the list below.
Flights San Juan — Chicago depart from Luis Muñoz Marín International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
A direct flight covers the 3,309 km distance in approximately 4–4.5 hours, depending on weather conditions and the specific arrival airport.
Regular flights are operated by United Airlines, American Airlines, as well as Spirit, Frontier, and Alaska Airlines.
Yes, there are about 23 flights per week on this route, including direct flights from several major carriers.
Flight prices are constantly changing; you can check the current minimum for your dates in the low-fare calendar on this page.
Flights from San Juan arrive at the main Chicago airports, including O'Hare (ORD) and Midway (MDW).
Where travelers fly most — pick a route and check prices
