Find Cheap Flights from San Jose to Chicago O'Hare International (SJC - ORD)

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Sat 11/18
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Good to Know

Low Season:
August
Best time to beat the crowds
2%
expected price decrease
High Season:
December
Most popular time to fly
3%
expected price increase
Average Price:
$379
(avg. price over the last 2 weeks)
Good Deal:
$268
or less (round trip)

When to Book Flights from San Jose to Chicago O'Hare International

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

Top tips for Finding a Cheap Flight

When looking for a cheap flight, consider that 25% of our users selected a flight on this route for $268 or less.
The cheapest flight from San Jose to Chicago O'Hare International was found 30 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
Morning departure is around 14% 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 O'Hare International Flights

How long does a flight from San Jose to Chicago O'Hare International take?
An average nonstop flight takes 4h 05m, covering a distance of 1825 miles.
How many flights are there between San Jose and Chicago O'Hare International?
There are 163 (nonstop) flights between San Jose and Chicago O'Hare International per week, averaging 23 per day.
Which airlines provide the cheapest flights from San Jose to Chicago O'Hare International?
In the past 3 days, the cheapest round-trip tickets were found on Multiple Airlines ($105), Frontier ($125) and United ($387).
Do I need a passport to fly between San Jose and Chicago O'Hare International?
No.
Which airlines fly most frequently between San Jose and Chicago O'Hare International?
American Airlines (6 times daily), British Airways (6 times daily), United (4 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly San Jose to Chicago O'Hare International?
For San Jose to Chicago O'Hare International, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago O'Hare International back to San Jose, the best deals are generally found on Wednesday, with Monday being the most expensive.

Book cheap flights from San Jose to Chicago O'Hare International (round-trip)

Airports
Origin
San Jose
$105
only
$105
Destination
Chicago
$105
only
$105
Mon, Dec 4
SJC
ORD
20h 27m
Mon, Dec 11
ORD
SJC
8h 00m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Dec 2
SJC
ORD
13h 10m
Tue, Dec 5
ORD
SJC
6h 50m
Trip: 4 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PVD
TPA
Excellent 9.3

Cheap, comfortable and friendly staff

Getting off the plane took forever on both legs.

FSD
DEN
Okay 4.6

The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late

LGA
MIA
Mediocre 3.6

Flight Very late , when departure already at night Uncomfortable seats $45 for a bag and I have drop it off myself after pay

MIA
CVG
Good 6.0

More snack/food options

PBI
ISP
Mediocre 2.0

Was unable to make it

Thu, Dec 14
SJC
ORD
27h 12m
Mon, Dec 18
ORD
SJC
8h 00m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Nov 30
SJC
ORD
19h 55m
Sat, Dec 2
ORD
SJC
13h 35m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PHL
MIA
Excellent 10.0

Same as all the other airlines in my opinion. Just way more afreoadable.

MIA
PHL
Okay 5.6

Flight was on time. The flight was fast and the crew was helpful and courteous

It was cramped. Couldn't recline back. Was only offered water

MIA
CVG
Good 6.0

More snack/food options

MIA
ISP
Excellent 8.5

The terminal was empty. Plenty of seats. Boarding doesn't take long. Arrival at ISP is nice because it is small and empty.

MCO
DEN
Okay 4.6

The seats were clean; the cabin looked very nice. The plane got me from point A to B safely. smoothest Lansing ever!

Flight was delayed 2.5 hours. No communication from the cockpit, 2 out of the 4 flight attendants we really crabby. Undersea storage was unusually small. I’m 5’8” and my knees were pressed against the seat in front of me and the seats are hard. My legs were numb for part of the trip.

Thu, Nov 30
SJC
ORD
19h 55m
Mon, Dec 4
ORD
SJC
8h 00m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 17
SJC
ORD
11h 02m
Tue, Jan 23
ORD
SJC
19h 59m
Trip: 7 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
DEN
ORD
Okay 5.3

Low cost

They make you pay for everything. Even peanuts. No entertainment.

LGA
MIA
Mediocre 3.6

Flight Very late , when departure already at night Uncomfortable seats $45 for a bag and I have drop it off myself after pay

MCO
DEN
Okay 4.6

The seats were clean; the cabin looked very nice. The plane got me from point A to B safely. smoothest Lansing ever!

Flight was delayed 2.5 hours. No communication from the cockpit, 2 out of the 4 flight attendants we really crabby. Undersea storage was unusually small. I’m 5’8” and my knees were pressed against the seat in front of me and the seats are hard. My legs were numb for part of the trip.

PHL
MIA
Excellent 10.0

Same as all the other airlines in my opinion. Just way more afreoadable.

MIA
CVG
Good 6.0

More snack/food options

Mon, Jan 22
SJC
ORD
13h 12m
Wed, Jan 24
ORD
SJC
13h 37m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 1
SJC
ORD
9h 25m
Mon, Feb 5
ORD
SJC
13h 37m
Trip: 5 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
DEN
SLC
Okay 5.6

Food, entertainment NA, didn’t use. Rest of flight uneventful, happy to say. Because this was so late due to previous leg of journey delayed, our planned transportation to hotel wa not available.

PHL
MIA
Excellent 10.0

Same as all the other airlines in my opinion. Just way more afreoadable.

MIA
PHL
Okay 5.6

Flight was on time. The flight was fast and the crew was helpful and courteous

It was cramped. Couldn't recline back. Was only offered water

MIA
ISP
Excellent 8.5

The terminal was empty. Plenty of seats. Boarding doesn't take long. Arrival at ISP is nice because it is small and empty.

PBI
ISP
Mediocre 2.0

Was unable to make it

Mon, Mar 19
SJC
ORD
4h 05m
Wed, Mar 21
ORD
SJC
4h 36m
Trip: 3 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 7 reviews
Overall
7.2
Boarding
7.3
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
LAX
Okay 4.0

Had xtra legroom and Wi-Fi

I paid the xtra $99 for the economy plus but my headphone jack didn’t work so I couldn’t watch a movie and my tray table was broken so I had to hold my drink and fumble with my food. The flight attendant tried to fix it but couldn’t. Made my 6 hour flight feel like 12 hours.

FAT
DEN
Excellent 8.0

Heavy Hispanic woman got ill and I was really worried she might pass away because she kept laying forward asleep or passed out on the back of the seat in front of her. Finally they found a doctor who was bilingual and he took great care of her. So bravo for that UA!

Heavy Hispanic woman got ill and I was really worried she might pass away because she kept laying forward asleep or passed out on the back of the seat in front of her. Finally they found a doctor who was bilingual and he took great care of her. So bravo for that UA!

SJC
ORD
Excellent 8.3

Staff nice and seat was comfortable.

The computers were down in SJC so everyone was waiting in line to check in and drop off luggage. It was a very long and slow process, but staff were friendly and professional even with difficult passengers. The thing that bugged me was they kept telling us not to worry and that the flight would be delayed so that we all could make it. I was the last one on the plane and I know there had to be at least 10 that didn't make it in time. I think the flight was only delayed by like 15min or so. I don't think they should tell people not to worry because the plane will wait for them, when it didn't wait for all. I get it that you want to also please those in the plane already and those waiting at destination so I'm not upset. Just giving feedback.

SJC
EWR
Mediocre 3.6

Arrived on time

Narrow seat

DCA
IAH
Good 7.3

Crew was great and helpful!

Not enough options for people with celiac.

Fri, Apr 20
SJC
ORD
5h 59m
Mon, Apr 23
ORD
SJC
6h 11m
Trip: 4 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PBI
ISP
Mediocre 2.0

Was unable to make it

MCO
DEN
Okay 4.6

The seats were clean; the cabin looked very nice. The plane got me from point A to B safely. smoothest Lansing ever!

Flight was delayed 2.5 hours. No communication from the cockpit, 2 out of the 4 flight attendants we really crabby. Undersea storage was unusually small. I’m 5’8” and my knees were pressed against the seat in front of me and the seats are hard. My legs were numb for part of the trip.

FSD
DEN
Okay 4.6

The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late

DEN
ORD
Excellent 10.0

On time. Very organized.

MIA
PHL
Okay 5.6

Flight was on time. The flight was fast and the crew was helpful and courteous

It was cramped. Couldn't recline back. Was only offered water

Sun, Apr 1
SJC
ORD
4h 16m
Sun, Apr 8
ORD
SJC
4h 35m
Trip: 8 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 14 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SJC
ORD
Excellent 9.6

efficient, courteous staff

SJC
ORD
Excellent 10.0

Flight boarded on time and landed 30 minutes early. Best part is the gate was open in Chicago so we truly arrived early. Flight crew was great too. Very helpful and courteous.

Nothing.

SJC
ORD
Good 7.3

Ease of boarding and on time flights

Leg room and entertainment

SJC
ORD
Good 6.0

The plane had several problems mechanically. After we boarded we spent another hour waiting for the problems to be repaired. It added an extra hour to sitting.

SJC
ORD
Mediocre 2.0

Water and sodas

Onboarding crew made me pay 200 usd for extra weight without telling me that I could move lbs from one bas to another and pay less.

Wed, May 9
SJC
ORD
6h 00m
Sat, May 12
ORD
SJC
6h 15m
Trip: 4 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MCO
DEN
Okay 4.6

The seats were clean; the cabin looked very nice. The plane got me from point A to B safely. smoothest Lansing ever!

Flight was delayed 2.5 hours. No communication from the cockpit, 2 out of the 4 flight attendants we really crabby. Undersea storage was unusually small. I’m 5’8” and my knees were pressed against the seat in front of me and the seats are hard. My legs were numb for part of the trip.

LGA
MIA
Mediocre 3.6

Flight Very late , when departure already at night Uncomfortable seats $45 for a bag and I have drop it off myself after pay

MIA
CVG
Good 6.0

More snack/food options

DEN
SLC
Okay 5.6

Food, entertainment NA, didn’t use. Rest of flight uneventful, happy to say. Because this was so late due to previous leg of journey delayed, our planned transportation to hotel wa not available.

DEN
ORD
Excellent 10.0

On time. Very organized.

Fri, May 11
SJC
ORD
6h 00m
Mon, May 14
ORD
SJC
6h 15m
Trip: 4 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
FSD
DEN
Okay 4.6

The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late

DEN
ORD
Excellent 10.0

On time. Very organized.

MCO
DEN
Okay 4.6

The seats were clean; the cabin looked very nice. The plane got me from point A to B safely. smoothest Lansing ever!

Flight was delayed 2.5 hours. No communication from the cockpit, 2 out of the 4 flight attendants we really crabby. Undersea storage was unusually small. I’m 5’8” and my knees were pressed against the seat in front of me and the seats are hard. My legs were numb for part of the trip.

LGA
MIA
Mediocre 3.6

Flight Very late , when departure already at night Uncomfortable seats $45 for a bag and I have drop it off myself after pay

MIA
CVG
Good 6.0

More snack/food options

Mon, Dec 25
SJC
ORD
12h 33m
Thu, Jan 4
ORD
SJC
19h 56m
Trip: 11 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MIA
CVG
Good 6.0

More snack/food options

DEN
ORD
Excellent 10.0

On time. Very organized.

FSD
DEN
Okay 4.6

The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late

MIA
PHL
Okay 5.6

Flight was on time. The flight was fast and the crew was helpful and courteous

It was cramped. Couldn't recline back. Was only offered water

DEN
ORD
Okay 5.3

Low cost

They make you pay for everything. Even peanuts. No entertainment.

Thu, Nov 30
SJC
ORD
19h 55m
Sun, Dec 3
ORD
SJC
6h 50m
Trip: 4 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PHL
MIA
Excellent 10.0

Same as all the other airlines in my opinion. Just way more afreoadable.

MIA
ISP
Excellent 8.5

The terminal was empty. Plenty of seats. Boarding doesn't take long. Arrival at ISP is nice because it is small and empty.

FSD
DEN
Okay 4.6

The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late

MIA
CVG
Good 6.0

More snack/food options

PVD
TPA
Excellent 9.3

Cheap, comfortable and friendly staff

Getting off the plane took forever on both legs.

Sat, Jan 20
SJC
ORD
13h 14m
Mon, Jan 22
ORD
SJC
13h 37m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MIA
ISP
Excellent 8.5

The terminal was empty. Plenty of seats. Boarding doesn't take long. Arrival at ISP is nice because it is small and empty.

PVD
TPA
Excellent 9.3

Cheap, comfortable and friendly staff

Getting off the plane took forever on both legs.

PHL
MIA
Excellent 10.0

Same as all the other airlines in my opinion. Just way more afreoadable.

DEN
ORD
Excellent 10.0

On time. Very organized.

LGA
MIA
Mediocre 3.6

Flight Very late , when departure already at night Uncomfortable seats $45 for a bag and I have drop it off myself after pay

Fri, Feb 2
SJC
ORD
13h 14m
Wed, Feb 7
ORD
SJC
13h 37m
Trip: 6 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
LGA
MIA
Mediocre 3.6

Flight Very late , when departure already at night Uncomfortable seats $45 for a bag and I have drop it off myself after pay

MIA
ISP
Excellent 8.5

The terminal was empty. Plenty of seats. Boarding doesn't take long. Arrival at ISP is nice because it is small and empty.

DEN
ORD
Okay 5.3

Low cost

They make you pay for everything. Even peanuts. No entertainment.

DEN
ORD
Excellent 10.0

On time. Very organized.

FSD
DEN
Okay 4.6

The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late

Fri, Feb 9
SJC
ORD
13h 14m
Sun, Feb 11
ORD
SJC
6h 47m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PHL
MIA
Excellent 10.0

Same as all the other airlines in my opinion. Just way more afreoadable.

FSD
DEN
Okay 4.6

The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late

PBI
ISP
Mediocre 2.0

Was unable to make it

MIA
PHL
Okay 5.6

Flight was on time. The flight was fast and the crew was helpful and courteous

It was cramped. Couldn't recline back. Was only offered water

DEN
SLC
Okay 5.6

Food, entertainment NA, didn’t use. Rest of flight uneventful, happy to say. Because this was so late due to previous leg of journey delayed, our planned transportation to hotel wa not available.

Wed, Mar 28
SJC
ORD
10h 58m
Wed, Apr 4
ORD
SJC
13h 35m
Trip: 8 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PVD
TPA
Excellent 9.3

Cheap, comfortable and friendly staff

Getting off the plane took forever on both legs.

MIA
PHL
Okay 5.6

Flight was on time. The flight was fast and the crew was helpful and courteous

It was cramped. Couldn't recline back. Was only offered water

MCO
DEN
Okay 4.6

The seats were clean; the cabin looked very nice. The plane got me from point A to B safely. smoothest Lansing ever!

Flight was delayed 2.5 hours. No communication from the cockpit, 2 out of the 4 flight attendants we really crabby. Undersea storage was unusually small. I’m 5’8” and my knees were pressed against the seat in front of me and the seats are hard. My legs were numb for part of the trip.

DEN
ORD
Excellent 10.0

On time. Very organized.

MIA
ISP
Excellent 8.5

The terminal was empty. Plenty of seats. Boarding doesn't take long. Arrival at ISP is nice because it is small and empty.

Sun, Dec 24
SJC
ORD
20h 03m
Wed, Jan 3
ORD
SJC
17h 40m
Trip: 11 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 32923 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
DEN
ORD
Okay 5.3

Low cost

They make you pay for everything. Even peanuts. No entertainment.

MIA
ISP
Excellent 8.5

The terminal was empty. Plenty of seats. Boarding doesn't take long. Arrival at ISP is nice because it is small and empty.

FSD
DEN
Okay 4.6

The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late

MIA
PHL
Okay 5.6

Flight was on time. The flight was fast and the crew was helpful and courteous

It was cramped. Couldn't recline back. Was only offered water

DEN
ORD
Excellent 10.0

On time. Very organized.

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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.