Cheap flights from San Jose (SJC) to Chicago (CHI)

SJC — CHI
Oct 4 — Oct 111

The best prices from San Jose to Chicago are usually found in October or January, booked 22 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

How to find the cheapest flight from San Jose (SJC) to Chicago (CHI)

All the information you need to plan the best SJC to CHI flight in 2022: compare San Jose to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

SJC - CHI

Price

$283 - $696

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inJuneHigh demand for flights, 35% potential price rise
Cheapest inOctoberBest time to find cheap flights, 38% potential price drop
Round-trip from$283From San Jose to Chicago (CHI)
One-way from$131One-way flight from San Jose to Chicago (CHI)

What is the cheapest day to fly round-trip from San Jose to Chicago?

Travelers have found that booking a Friday departure is the best way to save up to 17% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

How far in advance should I book a flight from San Jose to Chicago?

Travelers have found it’s best to book a flight 23 days in advance to save up to 42% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 23 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from San Jose to Chicago 1-2 weeks in advance for as low as $546, or $725 for flights within the next 24 hours.

What is the cheapest month to fly from San Jose to Chicago?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, October can be a great choice for travel to Chicago. Flights to Chicago from San Jose in October are about $455 on average during October, but can be found for as low as $164.

When is the cheapest time to fly from San Jose to Chicago (SJC - CHI)?

A simple way to save on the total cost of your ticket is to fly from San Jose to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight in the evening.

Cheap flights from San Jose to Chicago in September, October 2022

The best prices found for SJC to CHI flights for September, October
Oct 24 - Nov 3
SJC

San Jose

ORD

Chicago O'Hare Intl

2 stops

13h 39m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

13h 36m
$266

Multiple Airlines

Pick Dates

Deal found 9/26/22

Oct 19 - Oct 19
SJC

San Jose

ORD

Chicago O'Hare Intl

1 stop

9h 48m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

13h 36m
$267

Multiple Airlines

Pick Dates

Deal found 9/26/22

Oct 25 - Nov 1
SJC

San Jose

ORD

Chicago O'Hare Intl

2 stops

11h 46m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

13h 23m
$268

Multiple Airlines

Pick Dates

Deal found 9/27/22

San Jose to Chicago 2022 flight deals

Cheap flights to Chicago from San Jose found for this year
Nov 12 - Nov 16
SJC

San Jose

ORD

Chicago O'Hare Intl

1 stop

13h 20m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

13h 36m
$242

Multiple Airlines

Pick Dates

Deal found 9/26/22

Dec 1 - Dec 7
SJC

San Jose

ORD

Chicago O'Hare Intl

1 stop

8h 52m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

13h 35m
$244

Multiple Airlines

Pick Dates

Deal found 9/26/22

Dec 1 - Dec 5
SJC

San Jose

ORD

Chicago O'Hare Intl

1 stop

12h 45m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

8h 23m
$247

Multiple Airlines

Pick Dates

Deal found 9/26/22

Cheap United Airlines flights from San Jose to Chicago

Oct 25 - Nov 2
SJC

San Jose

ORD

Chicago O'Hare Intl

Nonstop

4h 16m
ORD

Chicago O'Hare Intl

SJC

San Jose

Nonstop

4h 51m
$262

United Airlines

Pick Dates

Deal found 9/29/22

Oct 18 - Oct 25
SJC

San Jose

ORD

Chicago O'Hare Intl

Nonstop

4h 16m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

7h 08m
$271

United Airlines

Pick Dates

Deal found 9/29/22

Oct 18 - Oct 25
SJC

San Jose

ORD

Chicago O'Hare Intl

1 stop

6h 24m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

8h 43m
$280

United Airlines

Pick Dates

Deal found 9/29/22

  • If you’re traveling from San Jose to Chicago, one of the more common airlines traveling that route is United Airlines. Flights from United Airlines traveling this route typically cost $627.68 RT. This price is typically 42% more expensive than other airlines that offer San Jose to Chicago flights. When booking this route, the cheapest RT price found was $404. The most popular departure airport in San Jose when flying to Chicago is San Jose Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from San Jose to Chicago, United Airlines flights are 20% more popular than any other airline flying that same route.

Cheap Delta flights from San Jose to Chicago

Nov 8 - Nov 15
SJC

San Jose

MDW

Chicago Midway

1 stop

8h 34m
MDW

Chicago Midway

SJC

San Jose

1 stop

9h 15m
$280

Delta

Pick Dates

Deal found 9/29/22

Nov 8 - Nov 15
SJC

San Jose

ORD

Chicago O'Hare Intl

2 stops

12h 48m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

6h 39m
$284

Delta

Pick Dates

Deal found 9/29/22

Nov 8 - Nov 15
SJC

San Jose

ORD

Chicago O'Hare Intl

2 stops

12h 48m
ORD

Chicago O'Hare Intl

SJC

San Jose

2 stops

9h 58m
$289

Delta

Pick Dates

Deal found 9/29/22

  • One of the most popular airlines traveling from San Jose to Chicago is Delta. Flights from Delta traveling this route typically cost $531.20 RT. This price is typically 53% cheaper than other airlines that offer San Jose to Chicago flights. When booking this route, the cheapest RT price found was $178. San Jose Airport is the most common San Jose airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from San Jose to Chicago, Delta flights are 19% more popular than any other airline flying that same route.

Non-stop flights to Chicago from San Jose

Save time with San Jose to Chicago direct flight deals
Oct 25 - Nov 2
SJC

San Jose

ORD

Chicago O'Hare Intl

Nonstop

4h 16m
ORD

Chicago O'Hare Intl

SJC

San Jose

Nonstop

4h 51m
$262

United Airlines

Pick Dates

Deal found 9/29/22

Nov 1 - Nov 10
SJC

San Jose

ORD

Chicago O'Hare Intl

Nonstop

4h 16m
ORD

Chicago O'Hare Intl

SJC

San Jose

Nonstop

4h 51m
$277

United Airlines

Pick Dates

Deal found 9/27/22

Oct 25 - Nov 5
SJC

San Jose

ORD

Chicago O'Hare Intl

Nonstop

4h 16m
ORD

Chicago O'Hare Intl

SJC

San Jose

Nonstop

4h 51m
$292

United Airlines

Pick Dates

Deal found 9/27/22

Last minute flights from San Jose to Chicago

Late deals on return flights to Chicago from San Jose, departing today and this week
Oct 5 - Oct 11
SJC

San Jose

ORD

Chicago O'Hare Intl

2 stops

11h 54m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

13h 36m
$303

Multiple Airlines

Pick Dates

Deal found 9/26/22

Oct 5 - Oct 11
SJC

San Jose

ORD

Chicago O'Hare Intl

1 stop

7h 58m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

13h 36m
$316

Multiple Airlines

Pick Dates

Deal found 9/26/22

Oct 4 - Oct 18
SJC

San Jose

ORD

Chicago O'Hare Intl

2 stops

11h 54m
ORD

Chicago O'Hare Intl

SJC

San Jose

1 stop

13h 36m
$318

Multiple Airlines

Pick Dates

Deal found 9/27/22

One-way flights to Chicago from San Jose

The cheapest one-way flights from San Jose to Chicago
Oct 26
SJC

San Jose

RFD

Chicago Greater Rockford

2 stops

14h 22m
$113

Multiple Airlines

Pick Dates

Deal found 9/27/22

Nov 1
SJC

San Jose

ORD

Chicago O'Hare Intl

1 stop

20h 53m
$125

Multiple Airlines

Pick Dates

Deal found 9/27/22

Nov 9
SJC

San Jose

ORD

Chicago O'Hare Intl

1 stop

10h 50m
$127

Multiple Airlines

Pick Dates

Deal found 9/27/22

Related info for your journey

Useful info, stats and facts about San Jose to Chicago flights.

What airport do you fly from for flights from San Jose to Chicago?

Located just 2.9 mi from the city center, San Jose is the airport most travelers will use when flying to Chicago from San Jose. Booking flights from San Jose (SJC) to Chicago should be relatively easy as there are 8 daily outbound flights to Chicago from 9 different airlines.

Which airlines flying from San Jose to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from San Jose to Chicago have new flexible policies in place due to COVID-19. United Airlines, American Airlines, and Delta are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

Can I find flights from San Jose to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from San Jose to Chicago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $244, but on average you can expect to pay $268.

Are there nonstop flights from San Jose to Chicago for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from San Jose to Chicago under $300. A good price for a nonstop flight from San Jose to Chicago is less than $334.

Are there last-minute flights available from San Jose to Chicago for under $400?

There are currently 20+ open flights from San Jose to Chicago within the next 7 days for less than $400.

What days are nonstop flights available from San Jose to Chicago?

Nonstop flights are available for this route on the following days: Thursday, Friday.

How many flights depart from San Jose to Chicago on average per day?

On average, you can expect to see 1 flight from San Jose to Chicago a day.
Early Morning (Midnight to 6am) - 100% of flight departures

How long is the flight from San Jose to Chicago?

Airlines like United Airlines and Delta fly from San Jose to Chicago in about 4h 16m. The time it takes to get you to your destination can typically vary by up to 4h 18m. Airlines will cover a distance of 1835 mi. This flight may include one or multiple stops.

What are the cheapest airlines flying from San Jose to Chicago round-trip?

Cheapflights users have booked flights from San Jose to Chicago round-trip from $262. Another airline that can offer you cheap pricing is Delta. You may be able to fly from San Jose to Chicago for 42% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from San Jose to Chicago one-way?

One-way options have recently been found by users for as low as $131 on United Airlines. Other airlines that offer cheap prices include American Airlines from $139 and Delta from $140 one-way.

What are the most popular routes from San Jose to Chicago?

While some choose either San Jose - Chicago Midway or San Jose - Chicago Greater Rockford, San Jose - Chicago O'Hare Intl is the most popular route from San Jose to Chicago.

What are the most popular airlines that fly from San Jose to Chicago?

Before booking your flight from San Jose to Chicago check out the most popular airlines for this route: Undisclosed Carrier, American Airlines or Alaska Airlines.

What are the cheapest flights from San Jose to Chicago?

Looking for the cheapest flight from San Jose to Chicago? While on average our users pay $498, our data indicates the cheapest price to be $159. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $242.

Alternative routes for San Jose to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from San Jose to Chicago

The chart below displays the airlines Cheapflights users traveling from San Jose to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$12Average$24FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Spirit AirlinesCheapest$110Average$341FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
American AirlinesCheapest$148Average$380FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Alaska AirlinesCheapest$166Average$369FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights
United AirlinesCheapest$178Average$531FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$179Average$486FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights

Hourly flight availability from San Jose to Chicago

See what time of day planes typically take off from San Jose to Chicago
12%of flight departuresEarly morningMidnight to 6 am
63%of flight departuresMorning6 am to noon
25%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from San Jose to Chicago

See how many times per day planes take to the skies headed from San Jose to Chicago
Sunday1daily flight
Monday12daily flights
Tuesday9daily flights
Wednesday10daily flights
Thursday11daily flights
Friday12daily flights
Saturday2daily flights