If you want a cheap flight from San Jose Costa Rica to Chicago, you've got three airlines to choose from. You can use the search box to filter your preferences, but we've found that the cheapest day to fly is 18 / Feb / 2025.
Make sure you use the search options above to search for flights to other airports in Chicago, not just Chicago O'hare International Airport. The more options you look at, the better your chance of finding a cheap deal. Just so you know, the flight typically takes 10 hrs.
There are about ten flights to or via Chicago every week, so you have plenty of options. Keep your eye out for flights with Air Canada, Aeromexico and JetBlue – these are the most popular airlines for flying to .
You can expect accommodation prices to be higher at this time of year too. Last-minute deals do crop up, but it's best to book everything in advance to avoid disappointment.
