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

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Looking for a cheap flight? 25% of our users found flights on this route for $263 or less.

FAQs for Booking Chicago Midway to San Jose Flights

How long does a flight from Chicago Midway to San Jose take?
An average nonstop flight takes 6h 35m, covering a distance of 1833 miles.
How many flights are there between Chicago Midway and San Jose?
There are 22 (nonstop) flights between Chicago Midway and San Jose per week, averaging 3 per day.
Which airlines provide the cheapest flights from Chicago Midway to San Jose?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($264)
Do I need a passport to fly between Chicago Midway and San Jose?
No.
Which airlines fly most frequently between Chicago Midway and San Jose?
Southwest (3 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to San Jose?
For Chicago Midway to San Jose, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from San Jose back to Chicago Midway, the best deals are generally found on Tuesday, with Thursday being the most expensive.

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

Airports
Origin
Chicago
$264
only
$264
Destination
San Jose
$264
only
$264
Tue, Jan 9
MDW
SJC
8h 05m
Wed, Jan 17
SJC
MDW
8h 26m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

Tue, Jan 23
MDW
SJC
8h 05m
Tue, Jan 30
SJC
MDW
6h 16m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

Tue, Feb 6
MDW
SJC
8h 57m
Tue, Feb 13
SJC
MDW
8h 44m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

Tue, Mar 6
MDW
SJC
6h 35m
Wed, Mar 7
SJC
MDW
8h 53m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Thu, Feb 22
MDW
SJC
10h 44m
Mon, Feb 26
SJC
MDW
9h 38m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Tue, Mar 20
MDW
SJC
6h 35m
Thu, May 3
SJC
MDW
6h 01m
Trip: 45 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Fri, Apr 27
MDW
SJC
9h 01m
Sat, May 5
SJC
MDW
8h 10m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

Fri, May 18
MDW
SJC
8h 50m
Mon, May 21
SJC
MDW
8h 53m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

GSO
ATL
Excellent 10.0

Plane nice and comfortable

Sat, Jun 2
MDW
SJC
8h 35m
Wed, Jun 13
SJC
MDW
9h 10m
Trip: 12 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

Sun, Dec 24
MDW
SJC
7h 00m
Thu, Dec 28
SJC
MDW
8h 21m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

Sat, Dec 23
MDW
SJC
7h 00m
Sat, Dec 30
SJC
MDW
8h 29m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

Sat, Dec 30
MDW
SJC
9h 08m
Wed, Jan 3
SJC
MDW
8h 26m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

*
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