Cheap flights from San Jose (SJC) to Chicago (CHI)
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 in | June | High demand for flights, 35% potential price rise |
|---|---|---|
| Cheapest in | October | Best time to find cheap flights, 38% potential price drop |
| Round-trip from | $283 | From San Jose to Chicago (CHI) |
| One-way from | $131 | One-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
San Jose
Chicago O'Hare Intl
2 stops
13h 39mChicago O'Hare Intl
San Jose
1 stop
13h 36mMultiple Airlines
San Jose
Chicago O'Hare Intl
1 stop
9h 48mChicago O'Hare Intl
San Jose
1 stop
13h 36mMultiple Airlines
San Jose
Chicago O'Hare Intl
2 stops
11h 46mChicago O'Hare Intl
San Jose
1 stop
13h 23mMultiple Airlines
San Jose to Chicago 2022 flight deals
Cheap flights to Chicago from San Jose found for this year
San Jose
Chicago O'Hare Intl
1 stop
13h 20mChicago O'Hare Intl
San Jose
1 stop
13h 36mMultiple Airlines
San Jose
Chicago O'Hare Intl
1 stop
8h 52mChicago O'Hare Intl
San Jose
1 stop
13h 35mMultiple Airlines
San Jose
Chicago O'Hare Intl
1 stop
12h 45mChicago O'Hare Intl
San Jose
1 stop
8h 23mMultiple Airlines
Cheap United Airlines flights from San Jose to Chicago
San Jose
Chicago O'Hare Intl
Nonstop
4h 16mChicago O'Hare Intl
San Jose
Nonstop
4h 51mUnited Airlines
San Jose
Chicago O'Hare Intl
Nonstop
4h 16mChicago O'Hare Intl
San Jose
1 stop
7h 08mUnited Airlines
San Jose
Chicago O'Hare Intl
1 stop
6h 24mChicago O'Hare Intl
San Jose
1 stop
8h 43mUnited Airlines
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
San Jose
Chicago Midway
1 stop
8h 34mChicago Midway
San Jose
1 stop
9h 15mDelta
San Jose
Chicago O'Hare Intl
2 stops
12h 48mChicago O'Hare Intl
San Jose
1 stop
6h 39mDelta
San Jose
Chicago O'Hare Intl
2 stops
12h 48mChicago O'Hare Intl
San Jose
2 stops
9h 58mDelta
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
San Jose
Chicago O'Hare Intl
Nonstop
4h 16mChicago O'Hare Intl
San Jose
Nonstop
4h 51mUnited Airlines
San Jose
Chicago O'Hare Intl
Nonstop
4h 16mChicago O'Hare Intl
San Jose
Nonstop
4h 51mUnited Airlines
San Jose
Chicago O'Hare Intl
Nonstop
4h 16mChicago O'Hare Intl
San Jose
Nonstop
4h 51mUnited Airlines
Last minute flights from San Jose to Chicago
Late deals on return flights to Chicago from San Jose, departing today and this week
San Jose
Chicago O'Hare Intl
2 stops
11h 54mChicago O'Hare Intl
San Jose
1 stop
13h 36mMultiple Airlines
San Jose
Chicago O'Hare Intl
1 stop
7h 58mChicago O'Hare Intl
San Jose
1 stop
13h 36mMultiple Airlines
San Jose
Chicago O'Hare Intl
2 stops
11h 54mChicago O'Hare Intl
San Jose
1 stop
13h 36mMultiple Airlines
One-way flights to Chicago from San Jose
The cheapest one-way flights from San Jose to Chicago
San Jose
Chicago Greater Rockford
2 stops
14h 22mMultiple Airlines
San Jose
Chicago O'Hare Intl
1 stop
20h 53mMultiple Airlines
San Jose
Chicago O'Hare Intl
1 stop
10h 50mMultiple Airlines
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.
Other flights from San Jose
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.
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 departures | Early morningMidnight to 6 am |
|---|---|
| 63%of flight departures | Morning6 am to noon |
| 25%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
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 | 1daily flight |
|---|---|
| Monday | 12daily flights |
| Tuesday | 9daily flights |
| Wednesday | 10daily flights |
| Thursday | 11daily flights |
| Friday | 12daily flights |
| Saturday | 2daily flights |