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

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from San Jose to Chicago are usually found in July or August, booked 25 days in advance, depart on a Wednesday or Saturday 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
$256 - $424
CHI
Temperature
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 inches

Popular in

December

High demand for flights, 23% potential price rise

Cheapest in

July

Best time to find cheap flights, 22% potential price drop

Round-trip from

$256

From San Jose to Chicago (CHI)

One-way from

$125

One-way flight from San Jose to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from San Jose to Chicago?

Travelers have found that booking a Tuesday departure is the best way to save up to 18% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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 in the afternoon. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight at noon.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, July can be a great choice for travel to Chicago. Flights to Chicago from San Jose in July are about $329 on average during July, but can be found for as low as $167.

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

Travelers have found it’s best to book a flight 24 days in advance to save up to 48% 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 24 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 $378, or $526 for flights within the next 24 hours.

Cheap flights from San Jose to Chicago in January, February 2022

The best prices found for SJC to CHI flights for January, February
2 Feb - 7 Feb
$176pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJC
San Jose
3 Feb - 14 Feb
$187pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJC
San Jose
11 Feb - 15 Feb
$191pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJC
San Jose

San Jose to Chicago 2022 flight deals

Cheap flights to Chicago from San Jose found for this year
2 Feb - 7 Feb
$176pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJC
San Jose
3 Feb - 14 Feb
$187pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJC
San Jose
11 Feb - 15 Feb
$191pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJC
San Jose

Non-stop flights to Chicago from San Jose

Save time with San Jose to Chicago direct flight deals
23 Apr - 27 Apr
$278pp
SJC
San Jose
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SJC
San Jose
6 May - 10 May
$288pp
SJC
San Jose
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJC
San Jose
31 Mar - 4 Apr
$292pp
SJC
San Jose
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SJC
San Jose

Last minute flights from San Jose to Chicago

Late deals on round-trip flights to Chicago from San Jose, departing today and this week
27 Jan - 7 Feb
$239pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJC
San Jose
27 Jan - 30 Jan
$304pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJC
San Jose
27 Jan - 7 Feb
$314pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
   
2 STOPS
SJC
San Jose

One-way flights to Chicago from San Jose

The cheapest one-way flights from San Jose to Chicago
2:00 am - 6:58 pm
Alaska Airlines
2 Stops
14h 58m
SJC - ORD
Alaska Airlines
$125
Gotogate
5:25 am - 5:18 pm
Delta
2 Stops
9h 53m
SJC - MDW
Delta
$137
Delta
2:48 am - 9:07 am
United Airlines
Nonstop
4h 19m
SJC - ORD
United Airlines
$139
United

Related info for your journey

Useful info, stats and facts about <span class="emphasized">San Jose</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From San Jose to Chicago

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 2 daily outbound flights to Chicago from 8 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. American Airlines, United 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 American Airlines with this kind of flexibility.

Can I find flights from San Jose to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from San Jose to Chicago for under $200. The cheapest flight booked recently is on Multiple Airlines for just $176, but on average you can expect to pay $212.

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 $344.

Are there last-minute flights available from San Jose to Chicago for under $300?

There are currently 20+ open flights from San Jose to Chicago within the next 7 days for less than $300.

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 $103 on Alaska Airlines. Other airlines that offer cheap prices include Delta from $132 and United Airlines from $139 one-way.

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 $541, our data indicates the cheapest price to be $96. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $176.

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: Major Airline, American Airlines or Alaska Airlines.

What are the most reliable airlines from San Jose to Chicago?

Before booking your flight to Chicago from San Jose, check out the most reliable airlines to get you to your destination on time: American Airlines (100%), Qatar Airways (100%), Alaska Airlines( 100%).

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.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from San Jose?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from San Jose need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from San Jose must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from San Jose are not required to quarantine after entering Chicago.

Do I need a test to fly back to San Jose from Chicago?

Returning to San Jose from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to San Jose.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering San Jose.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for San Jose to Chicago

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

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from San Jose to Chicago.
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing San Jose

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 7 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.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$100 $193 No cancel fee 62%
Spirit Airlines
$108 $269 No cancel fee 65%
Alaska Airlines
$108 $265 No cancel fee 75%
Delta
$127 $407 No cancel fee N/A
United Airlines
$129 $370 No cancel fee 69%
American Airlines
$153 $389 No cancel fee 71%
Southwest
$404 $628 No cancel fee 63%

Hourly flight availability from San Jose to Chicago

See what time of day planes typically take off from San Jose towards Chicago.
Morning 6 AM to noon 80% of SJC to CHI departures
Afternoon Noon to 6 PM 17% of SJC to CHI departures
Early morning Midnight to 6 AM 3% of SJC to CHI departures
Evening 6 PM to midnight 0% of SJC to CHI departures
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.
Sunday
3 daily flights
Monday
3 daily flights
Tuesday
3 daily flights
Wednesday
3 daily flights
Thursday
3 daily flights
Friday
3 daily flights
Saturday
0 flights
Home North America USA Illinois Chicago Cheap flights from San Jose to Chicago