Cheap flights from San Jose (SJC) to Chicago (CHI) from $56
This is the cheapest one-way flight price, found on 10/1. Prices may vary by date and flight preferences.
The best prices from San Jose to Chicago are usually found in January or March, booked 23 days in advance, depart on a Tuesday or Saturday and return on a Friday
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 2023: compare San Jose to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
Popular in | June |
|---|---|
Cheapest in | January |
Round-trip from | $207 |
One-way from | $56 |
SJC - CHI Price | $207 - $364 |
|---|---|
CHI Temperature | 23 - 73.4 °F |
CHI Rainfall | 1.7 - 4.9 inches |
What is the cheapest day to fly round-trip from San Jose to Chicago?
Travelers have found that booking a Monday departure is the best way to save up to 22% 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 36% 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 $579, or $742 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, January can be a great choice for travel to Chicago. Flights to Chicago from San Jose in January are about $525 on average during January, but can be found for as low as $275.
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 evening. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight in the morning.
Cheap Spirit Airlines flights from San Jose to Chicago
Check out some of the cheapest Spirit Airlines flights we've come across from San Jose to Chicago. Deals update often to give you more flight options matching your criteria
Cheap Delta flights from San Jose to Chicago
To aid your search, here are some of the cheapest Delta flights we've found from San Jose to Chicago. Deals are refreshing constantly so come back soon for more options.
Cheap San Jose to Chicago flights in October & November 2023
The best prices found for SJC to CHI flights for October, November
These are some of the best deals we've found on flights to Chicago in 2023 at this time. Check back soon for alternative fares.
San Jose to Chicago 2023 flight deals
Cheap flights to Chicago from San Jose found for this year
These are some of the best deals we've found on flights to Chicago in 2023 at this time. Check back soon for alternative fares.
Non-stop flights to Chicago from San Jose
Save time with San Jose to Chicago direct flight deals
For a shorter flight, select one of these non-stop flights from San Jose to Chicago. Users can also choose from other San Jose to Chicago flights by using the search form above.
San Jose to Chicago flights leaving soon
Late deals on return flights to Chicago from San Jose, departing today and this week
Have a look at some of the flights available from San Jose to Chicago departing last-minute. Tip: verify your flight details before completing your reservation.
One-way flights to Chicago from San Jose
The cheapest one-way flights from San Jose to Chicago
Users traveling one-way from San Jose to Chicago can select one of these great deals. For those needing a return trip from San Jose, there is a search form available above.
Find flights from San Jose to Chicago within your budget
Use the slider to find flights from San Jose to Chicago that fit your budget.
Fly from
Fly to
Budget
$123 - $302
Route
Depart
Return
Price
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Tue 10/31
2 stops11h 55m
Chicago Midway
Tue 11/7
1 stop22h 41m
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Wed 11/1
1 stop8h 50m
Chicago O'Hare Intl
Tue 11/7
1 stop7h 51m
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Mon 10/30
2 stops12h 50m
Chicago Midway
Mon 11/6
1 stop24h 17m
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Wed 11/1
1 stop15h 26m
Chicago Midway
Wed 11/8
2 stops14h 41m
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Tue 10/24
1 stop13h 20m
Chicago O'Hare Intl
Sat 10/28
1 stop9h 59m
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Tue 10/31
1 stop10h 44m
Chicago O'Hare Intl
Tue 11/7
1 stop7h 51m
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Wed 10/25
1 stop7h 28m
Chicago O'Hare Intl
Sun 10/29
1 stop9h 14m
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Wed 1/3
1 stop19h 30m
Chicago O'Hare Intl
Sat 1/6
1 stop17h 27m
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Sat 11/4
2 stops8h 03m
Chicago O'Hare Intl
Mon 11/6
1 stop9h 33m
Reviews of airlines servicing Chicago
Get a feel of what it's like to fly with Spirit Airlines, Delta and Alaska Airlines from San Jose to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
I appreciated that we departed & arrived on time. I was very cold on the plane, despite wearing 2 jackets, & will bring a blanket next time. I appreciated the hot tea & cookie I was served. I also appreciated that our luggage was not lost or damaged.
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 6 daily outbound flights to Chicago from 6 different airlines.
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 $123, but on average you can expect to pay $137.
Are there nonstop flights from San Jose to Chicago for under $400 on Cheapflights?
Cheapflights has at least 20 direct flights from San Jose to Chicago under $400. A good price for a nonstop flight from San Jose to Chicago is less than $511.
Are there last-minute flights available from San Jose to Chicago for under $200?
There are currently 20+ open flights from San Jose to Chicago within the next 7 days for less than $200.
What days are nonstop flights available from San Jose to Chicago?
Nonstop flights are available for this route on the following days: Monday, Wednesday, Thursday, Friday, Saturday.
How many flights depart from San Jose to Chicago on average per day?
On average, you can expect to see 5 flights 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 Spirit Airlines fly from San Jose to Chicago in about 8h 50m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 1835 mi.
What is the cheapest airline to fly from San Jose to Chicago round-trip?
Cheapflights users have booked flights from San Jose to Chicago round-trip from $127. You may be able to fly from San Jose to Chicago for 75% less than the average price by searching for this airline.
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: American Airlines, Alaska Airlines or Delta.
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 $950, our data indicates the cheapest price to be $117. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $154.
What does SJC to ORD mean?
San Jose Airport is SJC and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).
Other flights from San Jose
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
| 16%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 57%of flight departures | Morning6 am to noon |
| 27%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 | 2daily flights |
|---|---|
| Monday | 8daily flights |
| Tuesday | 7daily flights |
| Wednesday | 7daily flights |
| Thursday | 8daily flights |
| Friday | 8daily flights |
| Saturday | 2daily flights |
Fly with Cheapflights
What makes Cheapflights the go-to destination for all your flight needs
How does Cheapflights help users find flights from San Jose to Chicago?
When you search for this flight from San Jose to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
Why should you use Cheapflights to find cheap flight tickets from San Jose to Chicago?
Cheapflights helps you find that perfect flight to Chicago from San Jose by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Can Cheapflights find flights from San Jose to Chicago with no change fees?
Certainly. Search results for flights to Chicago from San Jose shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from San Jose to Chicago become cheaper?
Yes! Start tracking prices for San Jose to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, navigate to the search form above to perform a search, which will then prompt you for a valid email address to use the tool.