Cheap flights from San José to Chicago

Juan Santamaria
SJO
Chicago FSS
CHI

Flight deals from San José to Chicago

Below you can see the best deals on flights San José — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 19 August, from $300.

Top 10 cheap flights from San José to Chicago

Q6
Y4
F9
$ 305

San José — Chicago

07:00—15:59
28 Aug 2026
8 h 21 m
2 stops
Q6
VB
$ 309

San José — Chicago

07:00—11:00
4 Sep 2026
7 h 15 m
1 stop
Q6
Y4
F9
$ 316

San José — Chicago

07:00—15:59
31 Aug 2026
8 h 21 m
2 stops
Q6
Y4
F9
$ 321

San José — Chicago

07:00—15:59
1 Sep 2026
8 h 21 m
2 stops
Q6
VB
$ 322

San José — Chicago

07:00—11:00
1 Sep 2026
7 h 15 m
1 stop
Q6
Y4
F9
$ 324

San José — Chicago

07:00—00:49
6 Sep 2026
8 h 6 m
2 stops
Q6
Y4
$ 324

San José — Chicago

07:00—23:47
1 Sep 2026
7 h 2 m
1 stop
Q6
Y4
$ 325

San José — Chicago

07:00—05:52
3 Sep 2026
7 h 2 m
1 stop
Q6
Y4
$ 325

San José — Chicago

07:00—23:47
3 Sep 2026
7 h 2 m
1 stop
Q6
Y4
$ 325

San José — Chicago

07:00—23:47
4 Sep 2026
7 h 2 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the San José — Chicago flight

Looking for cheap flights from San José to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your San José — Chicago ticket online at the best price.

The route has direct flights — around 3 flights per week, flights are operated by United Airlines, a nonstop flight takes about 7 h 20 min, the distance between the cities is around 3,557 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $233Min. price
NovemberCheapest
AprilPeak season
YesDirect flights
3,557 kmDistance
7 h 20 minTravel time
1Airlines
3 / wkFlights

Flight schedule from San José to Chicago

The table shows direct flights from San José to Chicago on the selected date. The flight takes approximately 7 h 20 min. Regular flights are operated by United Airlines. Departures from Juan Santamaria 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.

Today
Any time
Last update: 08 Aug 2026

Flight ticket prices by day: San José — Chicago

Below is a calendar of the lowest flight ticket prices for San José — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $233 in November, and the most expensive are around $452 in April. 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.

 
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Prices by month

Average one-way fares from San José to Chicago by month. Tickets are usually cheapest in April (around $349) and priciest in December (about $512) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$431mediumMay$373lowSep$361low
Feb$361lowJun$419mediumOct$349low
Mar$454highJul$501highNov$396medium
Apr$349lowAug$408mediumDec$512high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in November and most expensive in April. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a San José — Chicago ticket

  • Book ahead: fares for San José — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Flights San José — Chicago operate on Sundays and Saturdays — keep that in mind when picking your travel dates.
  • The cheapest month to fly to Chicago is usually November — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the San José — Chicago route are operated by 1 airline; United Airlines runs the most flights (around 100% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    1x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight SJO → ORD1x/week
      Duration
      5h 35m
      Days
      MTWTFSS
    100.0%Open →

Cities and airports on the San José — Chicago route

Flights San José — Chicago depart from Juan Santamaria 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.

Departure

San José

SJO
Costa Rica
About the cityHow to get thereWeatherAll about the country Costa Rica
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the San José — Chicago flight

How long is the flight from San José to Chicago?

A nonstop San José — Chicago flight takes about 7 h 20 min — the distance between the cities is around 3,557 km.

How far is it from San José to Chicago?

The distance from San José to Chicago is about 3,557 km, which a nonstop flight covers in around 7 h 20 min.

Are there direct flights from San José to Chicago?

Yes, there are nonstop flights San José — Chicago — around 3 flights per week.

Which airlines fly from San José to Chicago?

Airlines operating San José — Chicago include United Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do San José — Chicago flights use?

Flights from San José depart from Juan Santamaria International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from San José to Chicago?

The price of a San José — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in November, and most expensive in April. Tickets typically cost between $233 and $452. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights San José — Chicago?

Flights San José — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is November. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from San José to Chicago?

To catch a low fare San José — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually November.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from San José

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Where else you can fly from Chicago

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