Find Cheap Flights from San Jose to Chicago (SJC - CHI)

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Good to Know

Low Season:
September
Best time to beat the crowds
3%
expected price decrease
High Season:
May
Most popular time to fly
16%
expected price increase
Average Price:
$340
(avg. price over the last 2 weeks)
Good Deal:
$248
or less (round trip)

When to Book Flights from San Jose to Chicago

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $248 or less.
The cheapest flight from San Jose to Chicago was found 23 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be April, May and June. The cheapest month to fly is September.
Morning departure is around 5% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking San Jose to Chicago Flights

How long does a flight from San Jose to Chicago take?
An average nonstop flight takes 4h 13m, covering a distance of 1839 miles.
How many flights are there between San Jose and Chicago?
There are 86 (nonstop) flights between San Jose and Chicago per week, averaging 12 per day.
Which airlines provide the cheapest flights from San Jose to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Frontier ($178), Multiple Airlines ($191) and Delta ($264).
Do I need a passport to fly between San Jose and Chicago?
No.
Which airlines fly most frequently between San Jose and Chicago?
United (4 times daily), Southwest (2 times daily), Iberia (2 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly San Jose to Chicago?
For San Jose to Chicago, Monday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago back to San Jose, the best deals are generally found on Tuesday, with Saturday being the most expensive.

Book cheap flights from San Jose to Chicago (round-trip)

Airports
Origin
San Jose
$178
only
$178
Destination
Chicago
$178
only
$178
$264
only
$264
Mon, Mar 5
SJC
ORD
13h 10m
Mon, Mar 19
ORD
SJC
13h 35m
Trip: 14 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33896 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
AUS
PHX
Good 6.0

Flight was delayed

LAX
DEN
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

MKE
LAS
Okay 5.3

It was clean, and the crew did great!

Way off schedule, way to tight of space, no way to sleep being such a late flight! As far as a beverage, they were out of everything!! Nice air line for quick trips,but to fly for 4 hrs at night from leaving at 12;00am, just impossible to sleep or really relax.

COS
SAN
Excellent 10.0

Comfortable and affordable

None

MCI
DEN
Excellent 10.0

Very smooth flight

Wed, Apr 25
SJC
ORD
8h 38m
Wed, May 9
ORD
SJC
13h 08m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 21
SJC
ORD
7h 01m
Wed, Mar 28
ORD
SJC
8h 07m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

JFK
CDG
Excellent 10.0

The food and the service

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Mon, Aug 27
SJC
ORD
6h 16m
Wed, Aug 29
ORD
SJC
6h 45m
Trip: 3 days
10.0ExcellentShow reviews
Overall 10.0 Excellent
Based on 1 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
MCO
Mediocre 2.3

I dispatched a guitar in a hard case. It was labeled fragile and sent to a separate compartment. The guitar was poorly treated and the case was broken all over. Very disappointing. On top of that I had requested window seat and got the middle seat. No food was served and there was no movies to watch or anything, considering this was a five hour flight

SJC
SJD
Okay 4.6

poor

SEA
DEN
Excellent 10.0

i wish Alaska would fly straight to Denver from Montana. I fly from Montana to Denver a lot and it ends up being a whole day of travel instead of a couple hour flight.

SJC
ORD
Excellent 10.0

Wonderful seat and attendants.

RDU
SEA
Excellent 8.3

The flight crew was incredibly sweet and helpful; one of them even gave me their personal TUMS when I said I didn't feel well.

The flight boarded 30 minutes early; I arrived to my gate at the time of when my ticket said boarding started, but they were already calling final boarding call for my flight. I completely panicked. The plane was clean but the seats are very close together and there were no complimentary snacks- even though it was a 6 hour flight. On my flight back from Seattle on Delta, we got a complimentary meal AND a complimentary snack. I was expecting my Alaskan flight to be better based on everything I'd heard from friends, but my return Delta flight showed Alaska up; it was a spacier plane with way more food offered.

Tue, Apr 10
SJC
ORD
22h 02m
Tue, Apr 17
ORD
SJC
15h 47m
Trip: 8 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33896 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MKE
LAS
Okay 5.3

It was clean, and the crew did great!

Way off schedule, way to tight of space, no way to sleep being such a late flight! As far as a beverage, they were out of everything!! Nice air line for quick trips,but to fly for 4 hrs at night from leaving at 12;00am, just impossible to sleep or really relax.

MIA
DEN
Excellent 10.0

On time Departure, Early Arrival. Excellent Flight Crew

Seats don't recline, tiny tray Table

COS
SAN
Excellent 10.0

Comfortable and affordable

None

AUS
PHX
Good 6.0

Flight was delayed

LAS
BNA
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

Tue, May 1
SJC
ORD
6h 36m
Thu, May 3
ORD
SJC
15h 44m
Trip: 3 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33896 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
LAX
DEN
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

MIA
DEN
Excellent 10.0

On time Departure, Early Arrival. Excellent Flight Crew

Seats don't recline, tiny tray Table

LAS
BNA
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

MCI
DEN
Excellent 10.0

Very smooth flight

COS
SAN
Excellent 10.0

Comfortable and affordable

None

Thu, Mar 1
SJC
ORD
20h 11m
Wed, Mar 7
ORD
SJC
7h 58m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 28
SJC
ORD
13h 06m
Tue, Mar 6
ORD
SJC
6h 36m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33896 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
LAX
DEN
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

MKE
LAS
Okay 5.3

It was clean, and the crew did great!

Way off schedule, way to tight of space, no way to sleep being such a late flight! As far as a beverage, they were out of everything!! Nice air line for quick trips,but to fly for 4 hrs at night from leaving at 12;00am, just impossible to sleep or really relax.

AUS
PHX
Good 6.0

Flight was delayed

COS
SAN
Excellent 10.0

Comfortable and affordable

None

LAS
BNA
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

Mon, Apr 30
SJC
ORD
8h 17m
Mon, May 7
ORD
SJC
18h 06m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 21
SJC
MDW
6h 21m
Tue, Mar 27
MDW
SJC
8h 38m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

JFK
CDG
Excellent 10.0

The food and the service

GDL
ATL
Excellent 9.6

Expensive food

Wed, Apr 11
SJC
MDW
8h 44m
Tue, Apr 17
MDW
SJC
8h 08m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

SLC
YYZ
Excellent 9.6

Z

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

Sat, Apr 14
SJC
ORD
8h 38m
Tue, Apr 17
ORD
SJC
15h 47m
Trip: 4 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33896 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
LAS
BNA
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

AUS
PHX
Good 6.0

Flight was delayed

LAX
DEN
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

ABQ
DEN
Mediocre 2.0

They had to fly in 2 plains to try and get us out. They didn’t offer meal vouchers until 51/3 hours into the delay.

MCI
DEN
Excellent 10.0

Very smooth flight

Sat, Apr 21
SJC
MDW
8h 47m
Sat, Apr 28
MDW
SJC
8h 42m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

GDL
ATL
Excellent 9.6

Expensive food

Wed, Jun 6
SJC
ORD
8h 47m
Thu, Jun 7
ORD
SJC
18h 51m
Trip: 2 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33896 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
LAS
BNA
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

MIA
DEN
Excellent 10.0

On time Departure, Early Arrival. Excellent Flight Crew

Seats don't recline, tiny tray Table

LAX
DEN
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

ABQ
DEN
Mediocre 2.0

They had to fly in 2 plains to try and get us out. They didn’t offer meal vouchers until 51/3 hours into the delay.

DEN
LAS
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

Wed, Aug 15
SJC
ORD
10h 20m
Sun, Aug 19
ORD
SJC
18h 00m
Trip: 5 days
10.0ExcellentShow reviews
Overall 10.0 Excellent
Based on 1 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
LIH
Excellent 10.0

Flt arrived early. The crew were all very friendly and the service was excellent.

ORD
SEA
Excellent 9.6

crew's upbeat attitude

very limited drink choices

SJC
ORD
Excellent 10.0

Wonderful seat and attendants.

SEA
MCO
Mediocre 2.3

I dispatched a guitar in a hard case. It was labeled fragile and sent to a separate compartment. The guitar was poorly treated and the case was broken all over. Very disappointing. On top of that I had requested window seat and got the middle seat. No food was served and there was no movies to watch or anything, considering this was a five hour flight

LAX
MEX
Mediocre 2.0

My luggage didn’t come on my flight. I was given a phone number to call for updates. I didn’t receive my bag until the following day. It was very unprofessional.

Tue, Jul 31
SJC
ORD
6h 16m
Tue, Aug 7
ORD
SJC
11h 12m
Trip: 8 days
10.0ExcellentShow reviews
Overall 10.0 Excellent
Based on 1 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
DEN
Excellent 10.0

i wish Alaska would fly straight to Denver from Montana. I fly from Montana to Denver a lot and it ends up being a whole day of travel instead of a couple hour flight.

PDX
SFO
Okay 4.3

The crew was funny and handled the delay nicely

No notice of 2 hour delay

SEA
LIH
Excellent 10.0

Flt arrived early. The crew were all very friendly and the service was excellent.

FAI
SEA
Excellent 9.6

Easy on off and let us sleep

ORD
SEA
Excellent 9.6

crew's upbeat attitude

very limited drink choices

Thu, May 3
SJC
ORD
4h 13m
Thu, May 10
ORD
SJC
4h 30m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 1
SJC
MDW
9h 10m
Tue, May 8
MDW
SJC
6h 13m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

Thu, May 3
SJC
ORD
6h 36m
Sun, May 6
ORD
SJC
15h 44m
Trip: 4 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33896 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MCI
DEN
Excellent 10.0

Very smooth flight

PHL
SJU
Good 6.0

boarding and treatment by staff wad excellent

$3 for a cup of coffee is outrageous.... other airlines at least include beverages and a snack (peanuts etc).

LAX
DEN
Mediocre 2.0

Checking my luggage and then re-checking my luggage !!! Very annoying and very inconvenient. This is not passenger / customer friendly !!!

MKE
LAS
Okay 5.3

It was clean, and the crew did great!

Way off schedule, way to tight of space, no way to sleep being such a late flight! As far as a beverage, they were out of everything!! Nice air line for quick trips,but to fly for 4 hrs at night from leaving at 12;00am, just impossible to sleep or really relax.

ABQ
DEN
Mediocre 2.0

They had to fly in 2 plains to try and get us out. They didn’t offer meal vouchers until 51/3 hours into the delay.

Sat, Jun 2
SJC
ORD
4h 13m
Tue, Jun 5
ORD
SJC
4h 30m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Show more results

San Jose to Chicago Flight Information

Avg. Flight Duration 4h 21m
Flights Arrive in Chicago
Flights Depart from San Jose
Flight Price $178
Distance 1839 miles
Airlines Frontier, Delta, Alaska Airlines
*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.