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Cheap flights from San Jose to Chicago

1 nonstop flight a week. Operated by United Airlines, about 5h 33m in the air, 2,218 mi (3,569 km). Tickets from $439, nonstop from $536.

Flights from San Jose to Chicago

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Filters

Best fares from San Jose to Chicago

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $305 24 December 2026, with a connection Cheapest nonstop $536 19 December 2026, United Airlines Cheapest weekend departure $345 Sat, 19 December 2026 Cheapest month December 2026 tickets from $305

San Jose to Chicago at a glance

flight time, from 5h 32m to 5h 35m
5h 33m
straight-line distance
2,218 mi (3,569 km)
flight a week
1
next flight
14 November
departure time
13:55
lowest price, with a connection, 4 January
$439
lowest nonstop price
$536
airline
1

San Jose to Chicago ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: December 2026, tickets from $305. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is January 2027: from $439. The average across months is $372.

San Jose to Chicago flight schedule

1 flight a week, 3 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
UA 1952
United Airlines
13:55 Juan Santamaria International, terminal M
19:28 , terminal 5
5h 33m
Sat
Boeing 737

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 17 December.

FlightDepartsArrivesDurationDaysAircraft
UA 1952
United Airlines
13:25 Juan Santamaria International, terminal M
18:57 , terminal 5
5h 32m
Seasonal
Boeing 737
UA 1952
United Airlines
12:25 Juan Santamaria International, terminal M
18:57 , terminal 5
5h 32m
Seasonal
Boeing 737
UA 1952
United Airlines
13:00 Juan Santamaria International, terminal M
19:35 , terminal 5
5h 35m
Seasonal
Boeing 737

Days of the week are taken from the schedule for the next 14 days; schedules change by season. The search shows seat availability and the price for your date.

Airlines flying San Jose to Chicago

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

United Airlines1 a week

Airports

Where flights from San Jose to Chicago depart and land

Departure from San Jose

Juan Santamaria International SJO

1 flight a week, terminal M, 9 mi (15 km) from the city centre

About the airport

When to visit Chicago

Weather by month

Best time to visit: May, June, July, August, September and October, +18° to +27° by day. In November it is +10° by day and +2° at night, with 7 rainy days.

Jan
0° −7° 10 days
Feb
+2° −6° 7 days
Mar
+9° 0° 12 days
Apr
+14° +5° 13 days
May
+19° +10° 11 days
Jun
+27° +17° 9 days
Jul
+27° +19° 12 days
Aug
+27° +19° 10 days
Sep
+24° +16° 7 days
Oct
+18° +10° 11 days
Nov
+10° +2° 7 days
Dec
+4° −3° 10 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Frequently asked questions

How long is the flight from San Jose to Chicago?
A nonstop flight takes 5 hours 33 minutes on average, from 5h 32m to 5h 35m depending on the flight.
How far is Chicago from San Jose?
2,218 mi (3,569 km) in a straight line between the cities.
Which airlines fly nonstop from San Jose to Chicago?
United Airlines (1 a week).
How many flights a day are there from San Jose to Chicago?
There are 1 a week, about 0.1 a day on average.
When are the first and last flights from San Jose to Chicago?
The flight departs at 13:55 (UA1952). Local time.
What is the cheapest month to fly from San Jose to Chicago?
December 2026: tickets from $305. The most expensive is January 2027, from $439.
What is the cheapest upcoming date to fly from San Jose to Chicago?
24 December 2026 (Thursday): from $305 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from San Jose to Chicago?
United Airlines: nonstop tickets from $536 on 19 December by recent searches. Prices change daily, so compare the sellers in the search.
Which San Jose airport do flights to Chicago leave from?
Juan Santamaria International (1 a week).