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

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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 2021: compare San Jose to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
SJC - CHI
Price
$256 - $424
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 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

One-way from

$128

One-way flight from San Jose to Chicago

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?

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

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

Find a great deal and save up to 10% by booking at least 20 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from San Jose to Chicago within the next two weeks, with the cheapest ticket starting at $137.

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

Flights from San Jose to Chicago lean towards being more expensive in December. Prices are generally better when you fly from San Jose to Chicago in April, with the cheapest ticket starting at $33.

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.

Cheap flights from San Jose to Chicago in May, June 2021

The best prices found for SJC to CHI flights for May, June
17 May - 24 May
$208pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SJC
San Jose
21 May - 24 May
$214pp
SJC
San Jose
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJC
San Jose
17 May - 24 May
$226pp
SJC
San Jose
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJC
San Jose

San Jose to Chicago 2021 flight deals

Cheap flights to Chicago from San Jose found for this year
17 May - 24 May
$208pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SJC
San Jose
21 May - 24 May
$214pp
SJC
San Jose
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJC
San Jose
31 Aug - 8 Sep
$215pp
SJC
San Jose
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SJC
San Jose

Non-stop flights to Chicago from San Jose

Save time with San Jose to Chicago direct flight deals
31 Aug - 8 Sep
$215pp
SJC
San Jose
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SJC
San Jose
21 Aug - 1 Sep
$230pp
SJC
San Jose
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJC
San Jose
23 Aug - 8 Sep
$235pp
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
17 May - 24 May
$208pp
SJC
San Jose
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SJC
San Jose
21 May - 24 May
$214pp
SJC
San Jose
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJC
San Jose
17 May - 24 May
$226pp
SJC
San Jose
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJC
San Jose

One-way flights to Chicago from San Jose

The cheapest one-way flights from San Jose to Chicago
6:55 pm - 1:02 am
American Airlines
Nonstop
4h 07m
SJC - ORD
American Airlines
10:44 am - 1:05 am
Frontier
1 Stop
12h 21m
SJC - ORD
Frontier
$133
Kiwi.com
4:55 pm - 2:00 am
Alaska Airlines
1 Stop
7h 05m
SJC - ORD
Alaska Airlines

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

Are flight prices decreasing from San Jose to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both San Jose and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from San Jose to Chicago to control the spread of COVID-19?

Alaska Airlines is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from San Jose to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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.

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.

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 $208, but on average you can expect to pay $232.

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 $276.

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.

Is San Jose weather warmer or cooler than Chicago?

Our data indicates that the weather will be 84 °F on average in the month of July. The temperature in Chicago is typically hotter than in San Jose. If you're traveling when the temperature is at its warmest, push to plan early, as flight price and availability will have an impact on your travels. For the best results, search for flights well in advance or after peak season.

How long is the flight from San Jose to Chicago?

American Airlines, United Airlines, and Delta can get you from San Jose to Chicago in just under 4h 07m. Your travel time can differ by up to 1h 56m. This flight may include one or multiple stops.

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

Frontier, at $214, was found to be the cheapest airline from San Jose to Chicago.Alternate airlines to your destination round-trip include United Airlines and American Airlines. You may be able to fly from San Jose to Chicago for 34% 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 $80 on Frontier. Other airlines that offer cheap prices include American Airlines from $108 and United Airlines from $112 one-way.

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.
Flight duration
4h 21m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing San Jose

Airports servicing Chicago

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%
Alaska Airlines
$108 $265 No cancel fee 75%
Spirit Airlines
$108 $269 No cancel fee 65%
United Airlines
$129 $370 No cancel fee 69%
American Airlines
$153 $389 No cancel fee 71%
Delta
$127 $407 No cancel fee N/A
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 100% of SJC to CHI departures
Early morning Midnight to 6 AM 0% of SJC to CHI departures
Afternoon Noon to 6 PM 0% 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
2 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
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