Cheap flights from San Jose (SJC) to Chicago (CHI) from $98
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
SJC — CHI
May 17 — May 241
From?
To?
1 adult, Economy
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 October or January, booked 86 days in advance, depart on a Wednesday or Saturday and return on a Saturday
Cheap flight deals from San Jose to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 12, 2024.
Popular in | March |
|---|---|
Cheapest in | October |
Round-trip from | $223 |
One-way from | $136 |
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 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 60 days in advance to save up to 431% 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 60 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 $354, or $587 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 March. For low rates, October can be a great choice for travel to Chicago. Flights to Chicago from San Jose in October are about $418 on average during October, but can be found for as low as $126.
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 12% on your trip compared to booking a flight in the morning.
Cheap Spirit Airlines flights from San Jose to Chicago
Explore cheap flight options specifically provided by Spirit Airlines for the route between San Jose and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 12, 2024.
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
Tue 6/44:40 pmSJC - ORD
3 stops23h 00mSpirit Airlines
Tue 6/112:57 pmORD - SJC
3 stops26h 53mSpirit Airlines
Deal found 5/11$191
Mon 6/109:12 pmSJC - ORD
1 stop7h 24mSpirit Airlines
Mon 6/179:54 amORD - SJC
1 stop13h 33mSpirit Airlines
Deal found 5/11$195
Sat 5/253:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Mon 6/36:53 pmORD - SJC
3 stops22h 57mSpirit Airlines
Deal found 5/11$198
Wed 5/299:35 amSJC - ORD
1 stop10h 20mSpirit Airlines
Sun 6/21:13 pmORD - SJC
1 stop26h 13mSpirit Airlines
Deal found 5/11$203
Sat 5/253:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Mon 6/31:13 pmORD - SJC
1 stop22h 28mSpirit Airlines
Deal found 5/11$206
Thu 5/307:00 amSJC - ORD
1 stop6h 44mSpirit Airlines
Thu 5/304:44 pmORD - SJC
1 stop6h 17mSpirit Airlines
Deal found 5/11$208
Wed 5/224:40 pmSJC - ORD
1 stop12h 00mSpirit Airlines
Tue 5/289:15 pmORD - SJC
3 stops38h 39mSpirit Airlines
Deal found 5/12$209
Wed 5/294:40 pmSJC - ORD
2 stops11h 20mSpirit Airlines
Thu 5/301:13 pmORD - SJC
2 stops24h 18mSpirit Airlines
Deal found 5/11$212
Wed 5/298:00 amSJC - ORD
1 stop6h 56mSpirit Airlines
Sun 6/210:57 pmORD - SJC
2 stops16h 29mSpirit Airlines
Deal found 5/11$213
Cheap Delta flights from San Jose to Chicago
Explore cheap flight options specifically provided by Delta for the route between San Jose and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 12, 2024.
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.
Wed 7/2411:40 amSJC - ORD
2 stops10h 14mDelta
Wed 7/317:00 amORD - SJC
1 stop8h 40mDelta
Deal found 5/12$309
Wed 8/712:05 pmSJC - MDW
1 stop7h 42mDelta
Wed 8/1410:11 amMDW - SJC
2 stops10h 40mDelta
Deal found 5/11$313
Wed 8/76:30 amSJC - ORD
2 stops10h 05mDelta
Wed 8/149:30 amORD - SJC
2 stops11h 21mDelta
Deal found 5/11$318
Mon 8/57:37 pmSJC - ORD
2 stops10h 39mDelta
Wed 8/147:30 amORD - SJC
1 stop8h 14mDelta
Deal found 5/11$326
Mon 8/510:55 pmSJC - ORD
1 stop7h 21mDelta
Tue 8/137:10 amORD - SJC
2 stops13h 41mDelta
Deal found 5/11$330
Tue 8/61:40 pmSJC - ORD
1 stop6h 16mDelta
Tue 8/137:30 amORD - SJC
1 stop12h 06mDelta
Deal found 5/11$334
Mon 8/57:37 pmSJC - ORD
2 stops9h 45mDelta
Wed 8/147:10 amORD - SJC
2 stops13h 41mDelta
Deal found 5/11$335
Wed 6/122:35 pmSJC - ORD
1 stop7h 23mDelta
Mon 7/12:10 pmORD - SJC
1 stop9h 56mDelta
Deal found 5/11$336
Tue 8/61:40 pmSJC - ORD
1 stop6h 16mDelta
Mon 8/127:30 amORD - SJC
1 stop16h 38mDelta
Deal found 5/11$350
Cheap San Jose to Chicago flights in May & June 2024
Find cheap flight options from San Jose to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,633,403 searches. Prices were last updated on May 12, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Tue 6/116:20 amSJC - ORD
2 stops15h 30mSpirit Airlines
Sat 6/1512:32 pmORD - SJC
1 stop12h 00mSpirit Airlines
Deal found 5/12$194
Wed 5/2212:21 pmSJC - ORD
2 stops16h 19mSpirit Airlines
Tue 5/2810:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 5/12$195
Sat 6/13:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Sat 6/812:32 pmORD - SJC
1 stop13h 27mSpirit Airlines
Deal found 5/12$198
Tue 5/284:40 pmSJC - ORD
1 stop11h 50mMultiple Airlines
Fri 5/318:30 pmORD - SJC
2 stops14h 46mMultiple Airlines
Deal found 5/12$200
Thu 5/308:46 pmSJC - ORD
1 stop7h 54mSpirit Airlines
Mon 6/37:52 pmORD - SJC
1 stop15h 49mSpirit Airlines
Deal found 5/12$202
Wed 5/294:40 pmSJC - ORD
2 stops11h 20mSpirit Airlines
Sat 6/17:30 amORD - SJC
1 stop10h 20mSpirit Airlines
Deal found 5/12$205
Fri 6/79:12 pmSJC - ORD
1 stop7h 12mSpirit Airlines
Tue 6/1110:58 pmORD - SJC
1 stop12h 31mSpirit Airlines
Deal found 5/12$206
Thu 6/67:00 amSJC - ORD
1 stop12h 17mSpirit Airlines
Tue 6/119:36 amORD - SJC
1 stop16h 23mSpirit Airlines
Deal found 5/12$208
Wed 5/224:40 pmSJC - ORD
1 stop12h 00mSpirit Airlines
Tue 5/289:15 pmORD - SJC
3 stops38h 39mSpirit Airlines
Deal found 5/12$209
San Jose to Chicago 2024 flight deals
Discover exclusive flight deals for travel between San Jose and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 12, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Tue 6/116:20 amSJC - ORD
2 stops15h 30mSpirit Airlines
Sat 6/1512:32 pmORD - SJC
1 stop12h 00mSpirit Airlines
Deal found 5/12$194
Wed 5/2212:21 pmSJC - ORD
2 stops16h 19mSpirit Airlines
Tue 5/2810:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 5/12$195
Sat 6/13:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Sat 6/812:32 pmORD - SJC
1 stop13h 27mSpirit Airlines
Deal found 5/12$198
Tue 5/284:40 pmSJC - ORD
1 stop11h 50mMultiple Airlines
Fri 5/318:30 pmORD - SJC
2 stops14h 46mMultiple Airlines
Deal found 5/12$200
Thu 5/308:46 pmSJC - ORD
1 stop7h 54mSpirit Airlines
Mon 6/37:52 pmORD - SJC
1 stop15h 49mSpirit Airlines
Deal found 5/12$202
Wed 5/294:40 pmSJC - ORD
2 stops11h 20mSpirit Airlines
Sat 6/17:30 amORD - SJC
1 stop10h 20mSpirit Airlines
Deal found 5/12$205
Fri 6/79:12 pmSJC - ORD
1 stop7h 12mSpirit Airlines
Tue 6/1110:58 pmORD - SJC
1 stop12h 31mSpirit Airlines
Deal found 5/12$206
Thu 6/67:00 amSJC - ORD
1 stop12h 17mSpirit Airlines
Tue 6/119:36 amORD - SJC
1 stop16h 23mSpirit Airlines
Deal found 5/12$208
Wed 5/224:40 pmSJC - ORD
1 stop12h 00mSpirit Airlines
Tue 5/289:15 pmORD - SJC
3 stops38h 39mSpirit Airlines
Deal found 5/12$209
Non-stop flights to Chicago from San Jose
Discover non-stop flight options from San Jose to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 12, 2024.
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.
Tue 10/86:35 amSJC - ORD
Nonstop4h 21mUnited Airlines
Fri 10/119:12 amORD - SJC
Nonstop4h 44mUnited Airlines
Deal found 5/11$321
Wed 6/1910:30 pmSJC - ORD
Nonstop4h 09mUnited Airlines
Mon 6/247:45 pmORD - SJC
Nonstop4h 40mUnited Airlines
Deal found 5/11$351
Fri 7/56:39 amSJC - ORD
Nonstop4h 09mUnited Airlines
Tue 7/98:15 pmORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 5/11$353
Wed 7/316:39 amSJC - ORD
Nonstop4h 09mUnited Airlines
Thu 8/18:02 pmORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 5/12$370
Fri 8/166:39 amSJC - ORD
Nonstop4h 09mUnited Airlines
Mon 8/199:15 amORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 5/12$375
Tue 8/66:39 amSJC - ORD
Nonstop4h 09mUnited Airlines
Wed 8/148:10 pmORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 5/11$379
Thu 7/186:21 amSJC - ORD
Nonstop4h 09mUnited Airlines
Sat 7/208:15 pmORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 5/11$380
Tue 6/186:22 amSJC - ORD
Nonstop4h 08mUnited Airlines
Fri 6/217:45 pmORD - SJC
Nonstop4h 40mUnited Airlines
Deal found 5/11$408
Mon 8/56:39 amSJC - ORD
Nonstop4h 09mUnited Airlines
Mon 8/128:02 pmORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 5/11$410
San Jose to Chicago flights leaving soon
Find last-minute flight options from San Jose to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 12, 2024.
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.
Wed 5/2212:21 pmSJC - ORD
2 stops16h 19mSpirit Airlines
Tue 5/2810:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 5/12$195
Wed 5/224:40 pmSJC - ORD
1 stop12h 00mSpirit Airlines
Tue 5/289:15 pmORD - SJC
3 stops38h 39mSpirit Airlines
Deal found 5/12$209
Wed 5/2212:21 pmSJC - ORD
2 stops16h 19mSpirit Airlines
Tue 5/289:15 pmORD - SJC
3 stops38h 39mSpirit Airlines
Deal found 5/12$219
Wed 5/228:00 amSJC - ORD
1 stop20h 40mSpirit Airlines
Sat 5/254:05 pmORD - SJC
1 stop6h 04mSpirit Airlines
Deal found 5/12$235
Wed 5/2212:21 pmSJC - ORD
2 stops16h 19mSpirit Airlines
Sat 5/257:30 amORD - SJC
1 stop14h 39mSpirit Airlines
Deal found 5/12$258
Sun 5/198:46 pmSJC - ORD
2 stops20h 17mMultiple Airlines
Tue 5/2110:52 pmORD - SJC
2 stops14h 39mMultiple Airlines
Deal found 5/12$275
Sun 5/1911:16 amSJC - ORD
1 stop20h 08mSpirit Airlines
Tue 5/2110:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 5/12$277
Wed 5/2212:21 pmSJC - ORD
3 stops17h 52mSpirit Airlines
Tue 5/289:15 pmORD - SJC
3 stops38h 39mSpirit Airlines
Deal found 5/12$285
Wed 5/2212:21 pmSJC - ORD
2 stops16h 19mSpirit Airlines
Sat 5/254:05 pmORD - SJC
2 stops21h 26mSpirit Airlines
Deal found 5/12$290
One-way flights to Chicago from San Jose
Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 12, 2024.
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.
Wed 6/126:00 amSJC - ORD
3 stops22h 00mSpirit Airlines
Deal found 5/10$98
Wed 6/198:04 pmSJC - ORD
1 stop8h 20mSpirit Airlines
Deal found 5/11$104
Wed 6/267:00 amSJC - ORD
2 stops26h 33mMultiple Airlines
Deal found 5/11$109
Wed 5/224:40 pmSJC - ORD
1 stop12h 00mSpirit Airlines
Deal found 5/10$111
Wed 6/126:00 amSJC - RFD
1 stop6h 50mMultiple Airlines
Deal found 5/10$114
Wed 6/197:00 amSJC - ORD
2 stops10h 06mMultiple Airlines
Deal found 5/11$114
Fri 7/57:50 amSJC - ORD
1 stop11h 27mSpirit Airlines
Deal found 5/12$116
Fri 7/57:50 amSJC - RFD
2 stops30h 00mMultiple Airlines
Deal found 5/11$118
Mon 5/274:40 pmSJC - ORD
1 stop12h 00mSpirit Airlines
Deal found 5/10$118
Find flights from San Jose to Chicago within your budget
Customize your flight search to find flights from San Jose to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 12, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$191 - $353
Route
Depart
Return
Price
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Tue 6/4
3 stops23h 00m
Chicago O'Hare Intl
Tue 6/11
3 stops26h 53m
$191
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Mon 6/10
1 stop7h 24m
Chicago O'Hare Intl
Mon 6/17
1 stop13h 33m
$195
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Sat 5/25
1 stop8h 10m
Chicago O'Hare Intl
Mon 6/3
3 stops22h 57m
$198
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Tue 5/28
1 stop11h 50m
Chicago O'Hare Intl
Fri 5/31
2 stops14h 46m
$200
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Mon 6/10
3 stops24h 33m
Chicago O'Hare Intl
Mon 6/17
2 stops29h 54m
$202
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Wed 5/29
1 stop10h 20m
Chicago O'Hare Intl
Sun 6/2
1 stop26h 13m
$203
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Sat 5/25
1 stop8h 10m
Chicago O'Hare Intl
Mon 6/3
2 stops17h 26m
$205
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Wed 7/24
2 stops10h 14m
Chicago O'Hare Intl
Wed 7/31
1 stop8h 40m
$309
San JoseChicago O'Hare Intl
SJC - ORD
SJCORD
San Jose
Fri 7/5
Nonstop4h 09m
Chicago O'Hare Intl
Tue 7/9
Nonstop4h 43m
$353
When is the best time to book a flight from San Jose to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from San Jose to Chicago. Price data was last updated on May 10, 2024.
The best time to book flights from San Jose to Chicago is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
When is the cheapest time to fly from San Jose to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Jose to Chicago. Price data was last updated on May 5, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their San Jose to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Average price of flights to Chicago by month
Plan your trip from San Jose to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from San Jose to Chicago is currently $111 while a round-trip flight costs $228. Price data was last updated on May 5, 2024.
Currently, February is the cheapest month in which you can book a flight from San Jose to Chicago (average of $244). Flying from San Jose to Chicago in June is currently the most expensive (average of $348). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$248
February
$244
March
$280
April
$258
May
$278
June
$348
July
$330
August
$274
September
$258
October
$248
November
$270
December
$248
Temperature and rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.
CHI Temperature | 23 - 73.4 °F |
|---|
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 12, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Delta and United 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.
9,152 reviews
Comfort
7.9
Entertainment
7.3
Overall
8.1
Food
7.3
Boarding
8.2
Crew
8.6
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
9,152 reviews
9,152 reviews
Comfort
7.9
Entertainment
7.3
Overall
8.1
Food
7.3
Boarding
8.2
Crew
8.6
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
10,745 reviews
9,152 reviews
Comfort
7.9
Entertainment
7.3
Overall
8.1
Food
7.3
Boarding
8.2
Crew
8.6
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
10,981 reviews
9,152 reviews
Comfort
7.9
Entertainment
7.3
Overall
8.1
Food
7.3
Boarding
8.2
Crew
8.6
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
14,608 reviews
9,152 reviews
Comfort
7.9
Entertainment
7.3
Overall
8.1
Food
7.3
Boarding
8.2
Crew
8.6
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
1,504 reviews
9,152 reviews
Comfort
7.9
Entertainment
7.3
Overall
8.1
Food
7.3
Boarding
8.2
Crew
8.6
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
Related info for your journey
Find useful and relevant information for your journey from San Jose to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for San Jose to ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from San Jose to Chicago
Discover the top 6 airlines that operate flights from San Jose to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 12, 2024.
Search flights from San Jose to Chicago by cabin class
Find flights from San Jose to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from San Jose to Chicago
Find hourly flight availability from San Jose to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 12, 2024.
| 53%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 47%of flight departures | Morning6 am to noon |
| 0%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Midnight
6 AM
Noon
6 PM
Weekly flight availability from San Jose to Chicago
Explore weekly flight availability from San Jose to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 12, 2024.
| Sunday | 2daily flights |
|---|---|
| Monday | 8daily flights |
| Tuesday | 7daily flights |
| Wednesday | 7daily flights |
| Thursday | 8daily flights |
| Friday | 8daily flights |
| Saturday | 2daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Fly with Cheapflights
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
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, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.