Find cheap flights from Chicago Midway Airport to San Jose

MDW - SJC

Find cheap flights from Chicago Midway Airport to San Jose

Search hundreds of travel sites at once for deals on flights to San Jose

Round-trip
Economy
Chicago (MDW)
San Jose
Thu 4/22
Thu 4/29
Any month
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Good to know

Low season

FebruaryBest time to beat the crowds with an average 49% drop in price.

High season

AugustMost popular time to fly with an average 49% increase in price.

Average price round-trip

$414(avg. price over the last 2 weeks)

Good deal round-trip

$306or less

Good deal one-way

$219or less

Book cheap flights from Chicago Midway Airport to San Jose

When to book flights from Chicago Midway Airport to San Jose

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $219 or less one-way and $306 or less round-trip.
  • High season is considered to be July, August and September. The cheapest month to fly is February.
  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Chicago Midway Airport to San Jose flights

Which airlines have a flexible cancellation policy for flights from Chicago Midway to San Jose due to COVID-19?

Are there San Jose travel restrictions currently due to Coronavirus?

How long does a flight from Chicago Midway Airport to San Jose take?

How many flights are there between Chicago Midway Airport and San Jose?

Which airlines provide the cheapest flights from Chicago Midway Airport to San Jose?

Do I need a passport to fly between Chicago Midway Airport and San Jose?

Which airlines fly most frequently between Chicago Midway Airport and San Jose?

What’s the cheapest day of the week to fly Chicago Midway Airport to San Jose?

How does KAYAK find such low prices on flights from Chicago Midway Airport to San Jose?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Jose?

What is the Hacker Fare option on flights from Chicago Midway Airport to San Jose?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to San Jose?

Top airline flying Chicago Midway to San Jose

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,182 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "Over a month ago I requested a seat with extra leg room due to a documented medical condition. My request was not granted and I was in pain most of the flight."

Pros: "Great crew, early arrival"
Cons: "Old screens, snacks getting smaller, too much ice in the drinks"

Cons: "Bag drop agent was not helpful."

Pros: "Nice on board crew."
Cons: "More arm & leg room in basic seating. Tray tables are flimsy and seem worn."

Pros: "I liked the choices of movies"
Cons: "The seats were dirty and the snack choices are not healthy at all."

Pros: "The staff was very nice and helpful with prechecking my bag at the gate."
Cons: "Food / snack choices are unhealthy and limited. The cabin was not clean when I got to my seat. There was trash in my pocket and crumbs on the ground."

Pros: "The crew was excellent."

Pros: "Great crew, easy process overall"
Cons: "Make 1st class cheaper and give free wifi!"

Pros: "Seat comfort"
Cons: "Lot of turbulence. Provided videos/entertainment without providing headphones"

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Pros: "The seats were very comfortable even though legroom was limited in the basic cabin."

Pros: "Was gud"

Pros: "Good crew."
Cons: "Very tight spaces. No tv."

Pros: "Comfy seats, quick service."
Cons: "If you are in Zone 3 or 4 you pretty much have to check in your bag back there is no more room. Which I don’t understand and is highly incovienent."

Pros: "Service by the Delta team"
Cons: "Seats not roomy enough"

Cons: "At least one hour late"

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Pros: "great service, easy to get on and off, snack options and drinks were all great"

Cons: "Put me on an Aeromexico plane without a seat. When I went to get seat assignments she gave me very last seat with a “window” she said. There was no window. I was absolutely closterphobic"

Cons: "Not much food offered on a long flight."

Pros: "Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations"
Cons: "The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes."

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "I was traveling alone with my (cranky) infant son and the crew members were kind and accommodating. Though the flight was delayed by almost 2 hours, the crew worked quickly to ready the replacement plane and the pilot made up time and got us to San Jose as quickly and safely as possible."
Cons: "The original plane had mechanical issues, which caused an almost two hour delay while waiting for a replacement plane to arrive. Since I was traveling alone with my young son, after an already long previous flight, it made for a more difficult trip."

Cons: "Sat by the exit seat so the door was a bit more chilly. No food. Small entertainment screens with audio bleed through."

Cons: "It’s was the best flight in my life"

Cons: "Was in seat 16A and got bumped to 12E. If you know Delta aircraft, that's exit row window, for the EC (more legroom) but middle. The problem is that nothing can compete with the exit row for leg room and being crammed between two guys isn't an upgrade either. Plus, due to proximity, got sick. And the flight was delayed leaving - due to the late arrival from ATL (Delta HQ) which had a power outage. And no video entertainment. No meals."

Pros: "On time arrival"
Cons: "Small aircraft. Loud engine noise. Biased treatment for tickets booked on non Delta sites"

Pros: "No vegetarian options in first class.. and go go wouldn5 hook up. Flight was an hour late...but that was ok."
Cons: "The pilot did a nice job of flying in and banking so we could see the view.."

Pros: "Almonds"
Cons: "Seat, did not get upgraded"

Pros: "Fast and comfortable"
Cons: "No tv but understanding"

Pros: "Crew was curious and quick to think of alternative solutions."
Cons: "The flight was way too hot. They didn't have enough A/C and we were all sweating up a storm on the flight. The flight was also scheduled to leave 15 min early, but we ended up leaving 15 minutes late, it was odd. One of the bathrooms was out of order too."

Cons: "Smooth"

Pros: "The flight was very on-time and it reached the destination even earlier than expected."

Pros: "I will know more on my flight back to my destination!"

Pros: "Hassle free left on time arrived early San Jose nice airport and drive to red wood city picturesque Staff friendly and cookies great"
Cons: "On this occasion I actually enjoyed it all"

Pros: "Flight was smooth and leg room great"
Cons: "A flight of four hours should have decent food. Too short connection times and inconsistent restaurants in the airports often leave me very hungry. Give us real healthy food onboard."

Pros: "The turkey sabdwhich was tasty. Good movies."
Cons: "Telling me the doors were going to close & I couldn't use the restroom prior to boarding. Here I was starving from flight delays. In reality the door stayed open another 15 mins & people boarded with their to go food."

Cons: "No trash bag in my seat for puking or bubblegum"

Pros: "Comfortable plane"
Cons: "Travelled with some guys straight out of the Hangover movies. Going to Vegas for a Bachelor party and ogling and making comments on the flight attendant and other passengers! Nothing delta can do about that, It's part of life..."

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "We didnt have food or entertainment because the flight was short."
Cons: "There was nothing that I didn't like."

Cons: "Poor leg room compared to jet blue"

Pros: "Comfortable seating and clean interior. Flight attendants are helpful and courteous."
Cons: "Flight takeoff delayed one hour. Boarding has zoning, but with no structural boarding process, resulted some later zoning customers blocking earlier zoning customers in a single line. Suggest using multiple labeled queue lines, like southwest."

Pros: "Got an upgrade to Comfort + Delta is the best major airline in USA for sure"

Cons: "2 of my 4 bags, which I checked in, were broken during my travel."

Cons: "after reaching the destination, it took a lot to open the airplane's doors and letting people out"

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway Airport to San Jose

Airlines flying from Chicago Midway Airport to San Jose have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago Midway Airport to San Jose

Mandatory masks

Masks required on board, masks provided on flights from Chicago Midway Airport to San Jose

Social distancing seating

Middle seats unavailable to book on flights from Chicago Midway Airport to San Jose

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago Midway Airport to San Jose

Book cheap flights from Chicago Midway Airport to San Jose

Recent round-trip flight deals

10/6
Wed
1 stop
Delta
8h 49m
MDW - SJC
10/11
Mon
1 stop
Delta
8h 47m
SJC - MDW
5/26
Wed
2 stops
Delta
13h 41m
MDW - SJC
5/29
Sat
2 stops
Delta
12h 43m
SJC - MDW
9/28
Tue
1 stop
Delta
13h 06m
MDW - SJC
10/4
Mon
1 stop
Delta
11h 23m
SJC - MDW
5/13
Thu
2 stops
Delta
11h 59m
MDW - SJC
5/17
Mon
2 stops
Delta
13h 26m
SJC - MDW
5/22
Sat
2 stops
Delta
11h 05m
MDW - SJC
6/2
Wed
2 stops
Delta
13h 10m
SJC - MDW
5/2
Sun
2 stops
Delta
10h 19m
MDW - SJC
5/4
Tue
2 stops
Delta
12h 11m
SJC - MDW
5/29
Sat
2 stops
Delta
10h 10m
MDW - SJC
6/5
Sat
2 stops
Delta
10h 13m
SJC - MDW
6/2
Wed
2 stops
Delta
13h 41m
MDW - SJC
6/7
Mon
2 stops
Delta
14h 02m
SJC - MDW
6/19
Sat
2 stops
Delta
15h 12m
MDW - SJC
6/23
Wed
1 stop
Delta
9h 02m
SJC - MDW
5/20
Thu
2 stops
Delta
12h 54m
MDW - SJC
5/24
Mon
2 stops
Delta
12h 43m
SJC - MDW
5/15
Sat
2 stops
Delta
11h 05m
MDW - SJC
5/17
Mon
2 stops
Delta
13h 26m
SJC - MDW
9/16
Thu
1 stop
Delta
9h 28m
MDW - SJC
9/19
Sun
1 stop
Delta
8h 47m
SJC - MDW
9/16
Thu
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Delta
9h 50m
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9/19
Sun
1 stop
Delta
8h 47m
SJC - MDW
5/21
Fri
2 stops
Delta
11h 59m
MDW - SJC
5/26
Wed
2 stops
Delta
12h 23m
SJC - MDW
6/22
Tue
1 stop
Delta
8h 10m
MDW - SJC
6/30
Wed
1 stop
Delta
9h 02m
SJC - MDW
6/3
Thu
2 stops
Delta
11h 59m
MDW - SJC
6/14
Mon
2 stops
Delta
10h 13m
SJC - MDW
5/15
Sat
2 stops
Delta
11h 05m
MDW - SJC
5/20
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2 stops
Delta
12h 23m
SJC - MDW
6/7
Mon
2 stops
Delta
9h 54m
MDW - SJC
6/9
Wed
2 stops
Delta
10h 13m
SJC - MDW
5/18
Tue
2 stops
Delta
11h 31m
MDW - SJC
5/22
Sat
2 stops
Delta
16h 52m
SJC - MDW
6/10
Thu
2 stops
Delta
9h 54m
MDW - SJC
6/14
Mon
2 stops
Delta
10h 13m
SJC - MDW
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Recent one-way flight deals

5/12
Wed
2 stops
Delta
11h 31m
MDW - SJC
5/12
Wed
2 stops
Delta
11h 59m
MDW - SJC
5/3
Mon
2 stops
Delta
11h 24m
MDW - SJC
6/4
Fri
2 stops
Delta
10h 29m
MDW - SJC
5/13
Thu
2 stops
Delta
11h 59m
MDW - SJC
6/26
Sat
1 stop
Delta
8h 10m
MDW - SJC
5/14
Fri
2 stops
Delta
10h 16m
MDW - SJC
6/4
Fri
2 stops
Delta
10h 29m
MDW - SJC
5/26
Wed
2 stops
Delta
11h 01m
MDW - SJC
8/12
Thu
1 stop
Delta
9h 28m
MDW - SJC
6/30
Wed
1 stop
Delta
8h 10m
MDW - SJC
5/17
Mon
3 stops
Delta
16h 12m
MDW - SJC
6/16
Wed
2 stops
Delta
9h 54m
MDW - SJC
7/16
Fri
1 stop
Delta
8h 10m
MDW - SJC
6/20
Sun
1 stop
Delta
8h 10m
MDW - SJC
6/28
Mon
1 stop
Delta
8h 10m
MDW - SJC
5/15
Sat
2 stops
Delta
11h 05m
MDW - SJC
5/2
Sun
2 stops
Delta
7h 46m
MDW - SJC
8/2
Mon
1 stop
Delta
8h 49m
MDW - SJC
4/29
Thu
3 stops
Multiple Airlines
23h 16m
MDW - SJC
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