Cheap flights from San José, San José Province to Chicago from $132
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San José, San José Province to Chicago departing on 5/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from San José, San José Province to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Avianca flights from San José, San José Province to Chicago
Our best Avianca deals on San José, San José Province to Chicago flight tickets
Spirit Airlines flights from San José, San José Province to Chicago
Our best Spirit Airlines deals on San José, San José Province to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from San José, San José Province to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between San José, San José Province and Chicago?
What is the cheapest month to fly to Chicago?
The month of August is, on average, the cheapest month to fly to Chicago from San José, San José Province, with most prices found around $396. If you’re not able to fly to Chicago in August, then July is your next best option. Flight prices from San José, San José Province to Chicago during July average around $422.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $330. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San José, San José Province to Chicago for around $655.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San José, San José Province to Chicago during this time can be as low as $335. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $618.
What is the cheapest San José Juan Santamaria Intl to Chicago flight route?
Fly from San José Juan Santamaria Intl to Chicago O'Hare Intl for the best San José Juan Santamaria Intl - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from San José, San José Province when booking 3 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $478 when searching 3 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San José, San José Province for as low as $379 on momondo.
What cabin class options are available on San José Juan Santamaria Intl to Chicago flights?
There are 3 cabin classes available to choose from on San José Juan Santamaria Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from San José Juan Santamaria Intl to Chicago?
Spirit Airlines, Avianca, and United Airlines are the most popular carriers operating from San José Juan Santamaria Intl to Chicago
What airlines fly to Chicago?
Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from San José, San José Province according to our data. Spirit Airlines is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
When to book flights from San José, San José Province to Chicago
Cheap San José, San José Province to Chicago (SJO to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San José, San José Province to Chicago
Best Price Found | $132 |
|---|---|
Fastest flight time | 5h 34m |
Direct flights | Mon, Thu, Sat and Sun |
Airports in Chicago | 2 airports |
How far is San José Juan Santamaria Intl to Chicago by plane?
A flight from San José Juan Santamaria Intl to Chicago will travel around 2215.9 mi. Flights usually cover this in 7h 26m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Chicago?
Prices for flights from San José Juan Santamaria Intl Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Chicago?
As of April 2025, there are 6 operators available to choose from for flights from San José Juan Santamaria Intl Airport to Chicago.
How old do you have to be to fly from San José Juan Santamaria Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from San José, San José Province to Chicago?
Based on momondo bookings for flights between San José, San José Province and Chicago, the leading plane model is Boeing 737 MAX 8, making up 61.90% of the total bookings. Other popular models include Airbus A350-900 with 7.62%, Airbus A320neo with 5.71%, and Airbus A330-200 with 4.76%.
What is the most popular airline from San José, San José Province to Chicago?
momondo data reveals that the most frequently booked airline on the route from San José, San José Province to Chicago is Spirit Airlines, representing 29% of all bookings. The subsequent popular airlines are United Airlines at 20%, American Airlines at 16%, and Copa Airlines at 14%.
Best airlines flying from San José, San José Province to Chicago
Compare and see reviews for airlines that fly from San José, San José Province to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $242 | Free Cancellation | Rating 6.3 7,963 reviews | |||
| PriceFrom $311 | Free Cancellation | Rating 7.5 1,414 reviews | |||
| PriceFrom $321 | Free Cancellation | Rating 6.7 2,317 reviews | |||
| PriceFrom $434 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $446 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $446 | Free Cancellation | Rating 7.4 8,696 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from San José to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from San José to Chicago for you.
Can I find flights from San José to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for San José to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from San José to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from San José.
I’m not ready to book a flight from San José to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from San José are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.