Compare fares, departure times, stops and baggage details for this route, then open the full search when you are ready to check current availability and complete booking.
SJOORDFri, 30 Oct
Fare checked before payment All fees shown upfront Transparent cancellation policy 24×7 booking support
Lowest fareCRC187,477Air Canada
Fastest8h 29mgate to gate
Options found124flights on this route
Find your flightSJO → ORD
Available Flights & Fares
Compare fares, timings and baggage. Pick the flight that suits your trip.
Night
00:00-05:59
CRC 239,016Air Canada at 05:35Morning
06:00-11:59
CRC 187,477Air Canada at 07:45Afternoon
12:00-17:59
CRC 224,419Delta Air Lines at 13:25Evening
18:00-23:59
CRC 260,546United Airlines at 22:28
Departure & Arrival Airport Details
San Jose (SJO)
Juan Santamaria Intl
Costa Rica
Chicago (ORD)
O Hare International
USA
Flights shown for 30 Oct 2026. View all flights opens the complete search result.
Smart travel dates
Holidays and peak dates for Chicago
Fares and hotel rates usually run higher around these dates. Booking earlier or moving your trip by a day or two often costs less.
Busiest periods: Summer travel (15 Jun – 31 Aug), Holiday season (18 Dec – 02 Jan).
12OctColumbus DayMondayPeak
12OctColumbus DayMondayPeak
12OctIndigenous Peoples' DayMondayPeak
11NovVeterans DayWednesdayPeak
26NovThanksgiving DayThursdayPeak
25DecChristmas DayFridayPeak
Fixed-date national holidays. Festivals that follow the lunar calendar shift each year and are not listed here, so check the exact date for your travel year.
Compare your journey
How to travel San Jose to Chicago
Ways to make this trip that you can book on FlyX, compared by price and journey time.
OptionFromJourney timeAvailabilityAction
Connecting flight₹39,559Longer, includes a stop124 options
7 airlines operate this route.
Road distance and coach duration are approximate estimates from the air distance, not a timetable.
Airlines flying from San Jose to Chicago
Compare fares, stops, baggage and refundability across the airlines flying this route.
UN
United Airlines Flights
from CRC 260,54657 flights
Fares from
CRC 260,546
Non-stop
None in these results
Departures
57 in the list above
AM
American Airlines Flights
from CRC 252,39945 flights
Fares from
CRC 252,399
Non-stop
None in these results
Departures
45 in the list above
AI
Air Canada Flights
from CRC 187,47716 flights
Fares from
CRC 187,477
Non-stop
None in these results
Departures
16 in the list above
DE
Delta Air Lines Flights
from CRC 224,4193 flights
Fares from
CRC 224,419
Non-stop
None in these results
Departures
3 in the list above
Route Overview & Flight Facts
Fastest flight duration
8h 29m · American Airlines
First departure of the day
05:10 · Air Canada
Last departure of the day
22:28 · United Airlines
Flight options found
124
Airport codes
San Jose–SJO, Chicago–ORD
Fares and timings are indicative. The exact price is confirmed with the airline when you search.
Flight Schedule, Timings & Airfare Insights
Daily Flight Schedule & Travel Duration
The search for Fri, 30 Oct found 124 flight options. The first flight leaves around 05:10 and the last around 22:28. The fastest flight takes about 8h 29m.
Morning vs Evening Departure Fares
Lowest fare by departure window: Morning from CRC 187,477, Afternoon from CRC 224,419, Night from CRC 239,016, Evening from CRC 260,546. These observations do not predict the cheapest departure window on other dates.
Cheapest Airfare & Best Time to Book
Search your travel dates to compare current fares. Prices change with airline seat availability.
One-Way vs Round-Trip Fare Comparison
Compare the complete cost and conditions of both options for your dates. A round-trip can have different fare and change rules from two one-way tickets. One booking may contain multiple airline PNRs; confirm baggage transfer and connection protection for separate tickets.
Online Web Check-In & Boarding Pass
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How to Book Cheap Flights on FlyX
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2
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3
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4
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5
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Destination & City Travel Guide
About Chicago
Chicago’s downtown Loop puts Millennium Park, the Art Institute and the Riverwalk within a manageable area. The lakefront creates a second axis for walking, while neighbourhoods farther out need transit time of their own. Passengers landing at O’Hare may be changing flights or visiting relatives in the wider region, so check whether an overnight hotel is near the airport or downtown. The CTA Blue Line runs from the airport into the city and avoids the road congestion that can affect a taxi.
Read more about Chicago
Tips for travellers from India
The Loop is useful for the Art Institute, Millennium Park and central rail links, while a hotel near O’Hare serves an early flight or suburban appointment. These bases are a substantial distance apart. The CTA Blue Line reaches the airport from downtown, but passengers arriving at Terminal 5 first need the airport connection to the main rail-access area. The airport train and an intercity rail departure from Union Station are separate arrangements.
Air India uses Terminal 5. United domestic flights and international departures use Terminal 1, while many international arrivals are processed through Terminal 5, so an onward connection can involve a building change. In the city, pair the Art Institute with Millennium Park rather than crossing to a distant neighbourhood between them. The Riverwalk offers another central route, while the lakefront extends far beyond the downtown section. The Obama Presidential Center opened to the public in June 2026 in Jackson Park, creating a museum outing on the South Side rather than another stop beside the Loop. Plan that visit as its own district trip. A river architecture cruise also has a specific departure dock, which should be matched to the walking route. Choose between a museum-heavy day and a longer lakefront walk before booking several timed attractions.
Best time to visit Chicago
May to June or September to October, about 12–25°C, for river and lake walks.
Places to visit in Chicago
Millennium ParkArt Institute of ChicagoChicago RiverwalkNavy PierMuseum CampusDevon Avenue
How to reach Chicago
By Air: O’Hare International Airport (ORD) is about 27 km northwest of downtown Chicago; the CTA Blue Line takes about 45 minutes to the Loop. Taxis and booked cars also operate.
By Rail: Chicago Union Station serves intercity trains; the CTA Blue Line links O’Hare with downtown.
By Road: Airport taxis and app-based cars use expressways; intercity coaches use downtown stops.
What to do in Chicago
Walk from Millennium Park to the Art Institute.
Follow the Chicago Riverwalk.
Take an architecture cruise on the Chicago River.
Explore the lakefront around Museum Campus.
Chicago airport information
O’Hare International Airport (ORD). Air India operates from O’Hare Terminal 5. United uses Terminal 1 for domestic flights and international departures, while international arrivals without preclearance generally use Terminal 5.
Why Book Your Flight with FlyX?
Compare the available San Jose to Chicago options by total price, stops, baggage and fare conditions. Search your dates for current availability, then review traveller details and the final price before paying.
Payment confirmation and ticket issuance are separate steps. If your booking is awaiting a PNR or ticket, follow its status and contact FlyX support when you need help. Your issued ticket contains the airline reference and itinerary. Change and cancellation charges depend on the purchased fare and any separately disclosed service fee.
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Frequently Asked Questions
Is it worth booking San Jose to Chicago flights in advance?
There is no guaranteed cheapest booking window. Compare your planned dates early, check nearby dates and consider baggage, connection time and change conditions as well as price. On the San Jose to Chicago dates shown on this page, the lowest fare is on a Friday at CRC 187,477. This can change from week to week.
How far is San Jose from Chicago by air?
The flying distance depends on the routing the airline selects. The flight cards above show duration and stop details for each result.
Are there non-stop flights from SJO to ORD?
Not on the dates shown here. Every San Jose to Chicago option on this page has at least one stop. Non-stop service can differ by season and by day, so check nearby dates before you decide.
Which airlines fly San Jose to Chicago?
United Airlines, American Airlines, Air Canada and Delta Air Lines are listed on this route for the dates shown here. Fares, baggage allowance and refund rules differ by airline and by fare type, so compare the fare conditions and not only the headline price.
How long is the flight from San Jose to Chicago?
Every option on this page has at least one stop, and the shortest total journey time is about 8h 29m including the layover. Non-stop service on this route can vary by season and by day.
What is the baggage allowance on San Jose to Chicago flights?
Allowance is set by the airline and the fare you pick, not by the route. Fares on this page include 2 Pieces and 1 Pieces. Cabin baggage is counted separately, and the exact allowance for the fare you choose is shown in the fare conditions before payment.
What is the cheapest San Jose to Chicago flight fare?
The lowest San Jose to Chicago fare on this page is CRC 187,477. Fares on the same dates run up to CRC 1,536,206, depending on airline, timing and fare type. Airline prices change often, so search your dates for the current fare.
What time do San Jose to Chicago flights depart?
On the dates shown here, the first departure is around 05:10 and the last around 22:28, local time at San Jose. Use the departure-time filter on the results above to narrow to a morning, afternoon or evening slot.
Why does the price change after clicking Book Now?
Airline seat inventory and fares change continuously. Selecting Book Now runs a live fare verification with the airline so the price you approve is the price you pay. If it has moved, you see the new figure before any payment.
Before you book this route
Check the airport codes SJO–ORD, local departure and arrival dates, and every connecting airport. Connections can have different document and baggage requirements from your final destination.
Where these fares come from
The fares, durations, stops and baggage shown here come from real airline search results for this route. They are examples for the dates on this page, not a full timetable and not a locked price. Run a search to see what is available for your own dates.
Fares shown are for departures on .
Check official travel requirements
Confirm passport, visa and transit rules for your nationality and full itinerary with the relevant government and operating airline. IATA travel-document information explains why requirements vary.
The SJO to ORD cards above show selected flight options. Airline prices and seat availability can move quickly, so the final fare is rechecked in the booking flow.
Before you book
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Lowest San Jose to Chicago airfare, in 30 days and in 90 days
Cheapest Fare
Fare
Date
Airline
Departure
Lowest Airfare
CRC 187,477
30/10/2026
Air Canada
07:45
Cheapest Airfare Within 30 Days
CRC 183,729
07/11/2026
Air Canada
07:45
Cheapest Airfare Within 90 Days
CRC 178,103
06/01/2027
Air Canada
07:45
Book San Jose to Chicago Flight Tickets on FlyX
FlyX lists each San Jose to Chicago flight in these results with its fare, departure time, stops, layover airport and baggage, so you can compare air tickets side by side. To find a cheap ticket, sort by price and check what baggage the fare includes. The fare is checked with the airline again before you pay.
San Jose to Chicago Flight Schedule and Timing
The search for these dates returned 124 flight options. The first departure from San Jose is at 05:10 and the last is at 22:28. Flights leave from Juan Santamaria Intl and land at O Hare International.
Flight Route Details & Analysis
Flight Details
Information
Route
San Jose to Chicago
Flight Duration
8h 29m - 38h 5m
Airport Codes
San Jose - SJO, Chicago - ORD
Total Flights Available
124 flights0 direct124 with layovers
First Flight Departure
Departs at 05:10
Last Flight Departure
Departs at 22:28
Early Morning Flights (12 AM - 8 AM)
41 flights0 direct41 with layovers
Morning Flights (8 AM - 12 PM)
11 flights0 direct11 with layovers
Afternoon Flights (12 PM - 4 PM)
56 flights0 direct56 with layovers
Evening Flights (4 PM - 8 PM)
1 flight0 direct1 with layover
Night Flights (8 PM - 12 AM)
15 flights0 direct15 with layovers
Airport Information & Terminals
SJO: San Jose airport. Airport access in San Jose depends on arrival time, terminal, hotel location and local traffic. Confirm the airport name on the ticket, then choose between official taxi, app cab, airport bus, rail or hotel transfer based on luggage and time of day.
ORD: Chicago airport system. Chicago flights commonly use O'Hare or Midway. O'Hare is a huge hub with rail access; Midway can be easier for some city-side trips. Winter weather and traffic should be part of the booking decision.
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Juan Santamaria Intl
O Hare International
