San Jose — flights from Chicago to San Jose

Flight Deals from Chicago to San Jose from $183

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Frontier AirlinesSouthwest AirlinesAmerican AirlinesAlaska AirlinesUnited Airlines+100s more
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Good to Know

Essential information to help you plan your flight from Chicago to San Jose.

Timing Your Trip

The best day, time of day, season and booking window for this route.

Price Drop Deals

Express Deal
Southwest AirlinesSouthwest Airlinesfound Oct 6
11/03/26
8:45 pm
MDWChicago Midway Airport
4h 45m
11/03/26
11:30 pm
OAKOakland International Airport
11/10/26
11:35 pm
SFOSan Francisco International Airport
4h 25m
11/11/26
6:00 am
MDWChicago Midway Airport
$227
Southwest AirlinesSouthwest Airlinesfound Oct 6
11/03/26
9:05 pm
MDWChicago Midway Airport
4h 50m
11/03/26
11:55 pm
SFOSan Francisco International Airport
11/10/26
11:35 pm
SFOSan Francisco International Airport
4h 25m
11/11/26
6:00 am
MDWChicago Midway Airport
$227
Southwest AirlinesSouthwest Airlinesfound Oct 6
11/03/26
5:45 pm
MDWChicago Midway Airport
6h 15mDENDenver International Airport
11/03/26
10:00 pm
OAKOakland International Airport
11/10/26
11:35 pm
SFOSan Francisco International Airport
4h 25m
11/11/26
6:00 am
MDWChicago Midway Airport
$237
Southwest AirlinesSouthwest Airlinesfound Oct 6
11/03/26
6:05 am
MDWChicago Midway Airport
6h 25mDENDenver International Airport
11/03/26
10:30 am
OAKOakland International Airport
11/10/26
11:35 pm
SFOSan Francisco International Airport
4h 25m
11/11/26
6:00 am
MDWChicago Midway Airport
$237
Flight plus hotel
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Southwest AirlinesSouthwest Airlinesfound Oct 6
11/03/26
6:05 am
MDWChicago Midway Airport
7h 5mDENDenver International Airport
11/03/26
11:10 am
SFOSan Francisco International Airport
11/10/26
11:35 pm
SFOSan Francisco International Airport
4h 25m
11/11/26
6:00 am
MDWChicago Midway Airport
$237
Alaska AirlinesAlaska Airlinesfound Oct 6
11/03/26
2:15 pm
ORDChicago O Hare Airport
7h 21mSANSan Diego International Airport
11/03/26
7:36 pm
SJCNorman Y. Mineta San Jose International Airport
11/10/26
9:39 am
SJCNorman Y. Mineta San Jose International Airport
7h 20mSANSan Diego International Airport
11/10/26
6:59 pm
ORDChicago O Hare Airport
$295
American AirlinesAmerican Airlinesfound Oct 6
11/03/26
5:00 pm
ORDChicago O Hare Airport
6h 34mPHXPhoenix Sky Harbor International Airport
11/03/26
9:34 pm
SJCNorman Y. Mineta San Jose International Airport
11/10/26
12:58 pm
SJCNorman Y. Mineta San Jose International Airport
7h 0mPHXPhoenix Sky Harbor International Airport
11/10/26
9:58 pm
ORDChicago O Hare Airport
$299
Southwest AirlinesSouthwest Airlinesfound Oct 6
11/03/26
8:45 pm
MDWChicago Midway Airport
4h 45m
11/03/26
11:30 pm
OAKOakland International Airport
11/10/26
8:30 am
OAKOakland International Airport
6h 50mLGBLong Beach /Daugherty Field/ Airport
11/10/26
5:20 pm
MDWChicago Midway Airport
$237
Alaska AirlinesAlaska Airlinesfound Oct 6
11/03/26
2:15 pm
ORDChicago O Hare Airport
7h 21mSANSan Diego International Airport
11/03/26
7:36 pm
SJCNorman Y. Mineta San Jose International Airport
11/10/26
7:37 am
SJCNorman Y. Mineta San Jose International Airport
9h 22mSANSan Diego International Airport
11/10/26
6:59 pm
ORDChicago O Hare Airport
$295
Southwest AirlinesSouthwest Airlinesfound Oct 6
11/03/26
9:05 pm
MDWChicago Midway Airport
4h 50m
11/03/26
11:55 pm
SFOSan Francisco International Airport
11/10/26
8:30 am
OAKOakland International Airport
6h 50mLGBLong Beach /Daugherty Field/ Airport
11/10/26
5:20 pm
MDWChicago Midway Airport
$237

Top Deals on flights from Chicago to San Jose

Chicago, US (CHI) - San Jose, US (SJC)

Frontier AirlinesFrontier Airlines

Nov 1

5:15 pm
ORDChicago O Hare Airport
22h 31m1 stop · LAS

Nov 2

1:46 pm
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$183

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

5:55 am
MDWChicago Midway Airport
6h 30m1 stop · DEN

Nov 1

10:25 am
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$218

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

5:55 am
MDWChicago Midway Airport
8h 10m1 stop · DEN

Nov 1

12:05 pm
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$218

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

9:55 am
MDWChicago Midway Airport
11h 15m1 stop · BUR

Nov 1

7:10 pm
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$223

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

9:25 pm
MDWChicago Midway Airport
12h 20m1 stop · LAS

Nov 2

7:45 am
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$223

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

9:20 pm
MDWChicago Midway Airport
12h 45m1 stop · SAN

Nov 2

8:05 am
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$223

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

9:45 pm
MDWChicago Midway Airport
13h 10m1 stop · PHX

Nov 2

8:55 am
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$223

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

8:45 am
MDWChicago Midway Airport
13h 20m1 stop · DEN

Nov 1

8:05 pm
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$223

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

9:55 am
MDWChicago Midway Airport
13h 20m1 stop · BUR

Nov 1

9:15 pm
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$223

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 1

9:25 pm
MDWChicago Midway Airport
13h 35m1 stop · LAS

Nov 2

9:00 am
SJCNorman Y. Mineta San Jose International Airport
Search More

as low as

$223

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 3

8:45 pm
MDWChicago Midway Airport
4h 45mNonstop

Nov 3

11:30 pm
OAKOakland International Airport
Search More

as low as

$227

Chicago, US (CHI) - San Jose, US (SJC)

Southwest AirlinesSouthwest Airlines

Nov 3

9:05 pm
MDWChicago Midway Airport
4h 50mNonstop

Nov 3

11:55 pm
SFOSan Francisco International Airport
Search More

as low as

$227

Best San Jose Hotel + Flight Packages

Chicago - San Jose packages

Best San Jose Hotel + Flight + Car Packages

Chicago - San Jose packages

When is the cheapest time to fly?

Cheapest in late January at about $276

Fares from Chicago to San Jose are lowest in late January, around $276, and February is the cheapest month overall, averaging $281. They peak in late December at about $357, $81 more than the low. The yearly average is $308.

JanFebMarAprMayJunJulAugSepOctNovDec$0$60$120$180$240$300$360$420
Show the data
When is the cheapest time to fly?
MonthAverage fareEarly monthLate month
January$281$287$276
February$281$276$287
March$320$308$332
April$307$315$299
May$305$299$311
June$333$323$342
July$338$341$335
August$305$316$294
September$293$289$298
October$295$305$286
November$303$295$311
December$336$313$357

How far in advance should I book?

Cheapest about 5 weeks out at $227

Book about 5 weeks before departure for the best fares from Chicago to San Jose, around $227. Booking in the final days before the flight costs about $339, $112 more. Booking six months ahead runs about $318.

1w2w1mo2mo3mo4mo5mo$0$40$80$120$160$200$240$280$320$360
Show the data
How far in advance should I book? (selected points, lowest and highest included)
Days before departureAverage fare
180 days$318
172 days$323
164 days$328
156 days$331
148 days$331
140 days$322
132 days$299
124 days$279
116 days$269
108 days$264
100 days$259
92 days$254
84 days$248
76 days$241
68 days$239
2mo$242
52 days$241
44 days$236
36 days$228
34 days$227
28 days$229
20 days$245
12 days$276
4 days$319
0 days$339
0 days$339

What's the cheapest day of the week to fly?

Wednesday is the cheapest day of the week to fly from Chicago to San Jose. At $349 it is 11% cheaper than the average day. Sunday is the most expensive day, 11% above average.

$434Sun$386Mon$394Tue$349Wed$368Thu$387Fri$419Sat
Show the data
What's the cheapest day of the week to fly?
DayAverage fare
Sun$434
Mon$386
Tue$394
Wed$349
Thu$368
Fri$387
Sat$419

When is the best time of day to fly?

Late night (9pm - 12am) is the cheapest time of day to fly from Chicago to San Jose. At $336 it is 12% cheaper than the average time. Morning (5am - 12pm) is the most expensive time, 16% above average.

$444Morning$350Midday$427Afternoon$361Evening$336Late Night
Show the data
When is the best time of day to fly?
Time of dayAverage fare
Morning$444
Midday$350
Afternoon$427
Evening$361
Late Night$336

What do round-trip flights from Chicago to San Jose cost?

Share of fares in each price range, adjusted to current prices.

1%$0to $15029%$150to $30034%$300to $45018%$450to $60012%$600to $7503%$750to $9002%$900and up
Show the data
What do round-trip flights from Chicago to San Jose cost?
Price rangeShare of fares
$0 to $1501%
$150 to $30029%
$300 to $45034%
$450 to $60018%
$600 to $75012%
$750 to $9003%
$900 and up2%
Methodology: learn how we calculate these charts

The charts “When is the cheapest time to fly?”, “How far in advance should I book?”, “What's the cheapest day of the week to fly?” and “What do round-trip flights from Chicago to San Jose cost?” are built from the prices Priceline customers actually paid for flights on this route over the past 12 months or more.

Where a route has too few bookings to fill every point in a chart, we borrow the shape of the curve from a group of routes with similar price behavior and fit it to the fares booked on this route.

Because past fares don’t reflect today’s market, we then adjust the historical prices for current conditions such as inflation and fuel costs, using the round-trip fares found in recent searches on this route.

The chart “When is the best time of day to fly?” is calculated directly from the fares found in recent searches, not from historical bookings.

Frequently Asked Questions

Everything you need to know about flying from Chicago to San Jose.

What is the typical flight duration from Chicago to San Jose?

Flights from Chicago to San Jose cover about 1,830 miles. The typical nonstop flight takes 4 hours 35 minutes outbound, while the return leg is 4 hours 10 minutes — about 25 minutes shorter heading east. Both directions are served daily by Southwest from Midway and United from O'Hare.
Methodology
Flight times and distances come from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). The typical flight time is the median scheduled block time across all carriers on the route, computed the same way in both directions so the difference reflects prevailing winds rather than any change in method. Distance is the great-circle distance between the two airports, so the actual flown track is typically 2-5% longer.

Are there any direct flights from Chicago to San Jose?

Southwest Airlines and United Airlines both fly non-stop from Chicago to San Jose. Southwest operates 14 weekly flights out of Midway, with departures around 10:05 AM and 8:50 PM, while United runs 7 weekly flights from O'Hare departing around 7:58 PM. Both carriers fly daily.
Methodology
Airlines and weekly frequencies are compiled from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). We count each operating carrier's scheduled weekly departures and the days it flies; where there is no nonstop service, connecting carriers are identified by linking scheduled nonstop segments through common hub airports. Where a median fare is shown for a carrier, it reflects the real fares Priceline users found on this route in the last 72 hours.

What are the ground transportation options in San Jose?

San Jose International Airport has a full range of ground transport: taxis at both terminals, app-based rideshares like Uber and Lyft with designated pickup spots, a free VTA Route 60 bus connecting to light rail and Caltrain, and a Rental Car Center with major agencies. The VTA light rail is the most-used public option for downtown, while rideshares are the most-used overall for door-to-door convenience. The fastest to downtown is a taxi or rideshare, typically under 10 minutes, given the airport is only 3.9 miles from the city center. Car rentals are strongest for exploring Silicon Valley beyond the city.
References

When is the cheapest time to fly from Chicago to San Jose?

Fares from Chicago to San Jose are lowest in late January, around $276. February is the cheapest month overall, averaging $281, followed by January ($281) and September ($293). July is the most expensive month at about $338, and fares peak in late December at about $357. The yearly average is $308. Fares are adjusted to current market conditions.
Methodology
Seasonal fares come from Priceline's own air booking-summary archive, analysed in-house and refreshed monthly. For each day of the year we take a representative round-trip fare, a blend of the 25th-percentile and average ticket price over the route's bookings, and smooth the series into a seasonal curve; the half-month low and high and the monthly figures quoted here are averages of that curve. Thin and international routes borrow their seasonal shape from the nearest busy routes, with the price level anchored to the route's own bookings.

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

Book about 5 weeks before departure for the best fares from Chicago to San Jose, around $227. Booking in the final days before the flight costs about $339, $112 more. Booking six months ahead runs about $318. Fares are adjusted to current market conditions.
Methodology
Booking-window guidance comes from the same monthly in-house analysis of Priceline's own air booking-summary archive. We aggregate the route's bookings by how many days before departure they were made, from about 180 days out to the day of travel, smooth the curve, and highlight the stretch of lead times with the lowest average fare. Thin and international routes borrow the curve shape from the nearest busy routes, anchored to the route's own price level. It reflects current fares and is refreshed monthly.

Are overnight (red‑eye) flights available from Chicago to San Jose?

No overnight or red-eye flights operate from Chicago to San Jose. Neither nonstop red-eyes nor connecting itineraries with an overnight long leg are scheduled on this route.
Methodology
Red-eye flights are identified from scheduled local departure and arrival times and block times in our flight-schedule database — built from published airline timetables and official schedule data, including U.S. Department of Transportation records for domestic routes. A flight counts as a red-eye when it departs in the afternoon or evening (3 p.m. or later local time) or in the early hours before 4 a.m., and is in the air at some point between midnight and 4 a.m. local time at both its departure airport and its arrival airport. An evening flight that lands before midnight at its destination is never counted, nor is a morning departure or a daytime long-haul that reaches the next calendar date only because of time zones. Each red-eye is labelled with its timing (for example, overnight and landing the next morning, or late-night and landing after midnight). For connecting itineraries the same rule is applied to the longer leg, from one representative day's flight search.

Which airlines usually operate this route from Chicago to San Jose?

Southwest Airlines flies nonstop from Chicago Midway to San Jose with 14 weekly flights, departing daily at 10:05 AM, 8:50 PM, and 8:55 PM. United Airlines operates daily nonstop service from Chicago O'Hare to San Jose, with a 7:58 PM departure. Southwest is not part of an alliance, while United is a member of Star Alliance.
Methodology
Airlines and weekly frequencies come from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). We count each operating carrier's scheduled weekly departures and the days it flies; where there is no nonstop service, connecting carriers are identified by linking scheduled nonstop segments through common hub airports. Where a typical fare is shown for a carrier, it is the median of the real fares Priceline users found on this route in the last 72 hours.

How reliable are on‑time arrivals on this route from Chicago to San Jose?

On the Chicago to San Jose route, Southwest Airlines is the most reliable carrier, with 75.8% of flights arriving within 15 minutes of schedule and a cancellation rate of just 0.5%. United Airlines follows at 68.0% on-time arrivals with a higher 1.6% cancellation rate. Southwest operates from Midway and United from O'Hare.
Methodology
On-time arrival and cancellation rates come from the U.S. Bureau of Transportation Statistics (BTS) Airline On-Time Performance dataset, which covers U.S. domestic routes only; a flight counts as on time when it arrives within 15 minutes of schedule. Carriers are ranked by arrival on-time rate on this route, and the carrier list itself comes from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI).

Which airport should I use in San Jose?

San Jose has one commercial airport, San Jose Mineta International Airport (SJC), located about 3 miles northwest of downtown. It is convenient for Silicon Valley business travel and is served by several major airlines.

How do I get to Chicago O'Hare International Airport from the city center?

The CTA Blue Line 'L' train is the most economical and popular way to reach O'Hare from downtown Chicago, running 24/7 and taking about 45 minutes for around $5. Taxis and ride-share services like Uber and Lyft offer quicker door-to-door trips of 30 to 40 minutes at a higher cost, typically $35 to $60. Metra's North Central Service and Pace buses provide additional public transit options, while driving and parking at O'Hare is also possible but generally the most expensive choice.
References

Are there hotels or sleeping facilities at San Jose airport?

San Jose Airport has no on-site hotel, but several nearby hotels offer free airport shuttles, including DoubleTree by Hilton, Hyatt Place San Jose Airport, Hyatt House, and Fairfield Inn & Suites by Marriott San Jose Airport, all within about a mile of the terminals. The nearest hotel is within a ten-minute drive, and most nearby properties provide complimentary shuttle service. There are no sleep cabins, pods, or day rooms at the airport itself.
References

What facilities and services are available to travelers at San Jose Mineta International Airport?

San Jose Mineta International Airport offers free Wi-Fi throughout the terminals. Travelers will find a revolving art exhibition and permanent public art displays, plus a public piano near Terminal B's baggage claim. Free ebooks are available for download near Gate 24 courtesy of the San Jose Public Library. Pet relief areas are located outside the terminal, north of ticketing. Restrooms include baby changing facilities. A filtered water machine is also available in the terminal.
References

Are there accessible services or children's facilities at the Chicago and San Jose airports?

At Chicago O'Hare International Airport, travelers with disabilities can arrange wheelchair assistance directly through their airline, and the airport offers sensory-friendly resources, Sunflower lanyards for non-visible disabilities, accessible restrooms, companion plus restrooms, and service animal relief areas. TSA Cares can be contacted for security screening accommodations, and an ADA coordinator is available by phone or email. At San Jose International Airport, wheelchair assistance, accessible parking, boarding assistance, and service animal relief areas are available, with arrangements made through your airline. Both airports provide mobility assistance and programs for travelers with disabilities.
References

What aircraft are typically used on flights from Chicago to San Jose?

Southwest Airlines, the leading carrier on the Chicago to San Jose route, flies Boeing 737 aircraft including the 737 MAX 8 and 737-700, while United Airlines operates the Airbus A319. These are the aircraft currently scheduled nonstop between the two cities.
Methodology
Aircraft types come from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). For U.S. routes the type is grounded in the tail number that actually operated the flight; elsewhere it comes from the airline's filed equipment code. Where the source does not commit to a specific variant we name the aircraft family (for example Airbus A320 family) rather than guess, and where no reliable type is on file the aircraft is omitted rather than estimated. Types describe typical scheduled equipment and can vary with seasonal or day-of-week assignments and last-minute swaps.

Which airline alliances serve flights from Chicago to San Jose?

Southwest Airlines and United Airlines are the carriers currently scheduled non-stop from Chicago to San Jose, with Southwest flying from Midway and United from O'Hare. United belongs to Star Alliance, while Southwest is a major carrier that belongs to no alliance; other alliances may reach San Jose from Chicago only via connections.
Methodology
Airlines and weekly frequencies are compiled from our flight-schedule database, which combines published airline timetables, U.S. government schedule data from the Bureau of Transportation Statistics (BTS), and observed flight operations from the EUROCONTROL/OpenSky Open Performance Data Initiative (OPDI). We count each operating carrier's scheduled weekly departures and the days it flies; where there is no nonstop service, connecting carriers are identified by linking scheduled nonstop segments through common hub airports. Where a median fare is shown for a carrier, it reflects the real fares Priceline users found on this route in the last 72 hours.

What are the best airport lounge options when departing from Chicago?

Chicago O'Hare International Airport offers a robust lounge scene across its terminals, with 16 airport lounges in total. United operates the most options, including the exclusive Polaris Lounge in Terminal 1 near Gate C18 for international first and business class passengers, plus five United Clubs spread through Terminals 1 and 2, with amenities like power outlets at every seat, complimentary hot meals, and phone rooms. American Airlines runs three Admirals Club lounges in Terminal 3, and its Flagship Lounge offers a step above with fewer crowds, dedicated service desks, and airport views. Delta's Sky Club is in Terminal 5 at Gate M13, and Terminal 5 also hosts the Air France Lounge, LOT Business Class Lounge, Swissport Lounge, and SAS Lounge. The LOT Business Lounge features floor-to-ceiling airport views, 165 seats, showers, charging stations, and workspaces, while the Air France Lounge opened in October 2025 near Gate M17.
References

Are same‑day changes or standby possible on this route?

Same-day changes and standby are generally permitted with flexible or higher-cabin fares on this route, while Basic Economy tickets offer no such option.