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The cheapest time of year to fly to San Jose from Chicago is January. Most expensive is May
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
Chicago to San Jose flights are approximately 9% more expensive in the morning than at noon
Alaska Airlines, American Airlines, and Delta are the most popular carriers operating from Chicago to San Jose
Chicago O'Hare Intl - San Jose
Fly from Chicago O'Hare Intl to San Jose for the best Chicago - San Jose flight prices
41 days before
The cheapest time to buy a flight from Chicago to San Jose is approximately 41 days to departure
When you’re planning your trip from Chicago to San Jose, the most popular airport-to-airport route is Chicago O'Hare Intl Airport to San Jose Airport. When booking your trip to San Jose, it is helpful to have an alternative airport to fly out of. The nearest airport to Chicago O'Hare Intl Airport is Chicago Midway Airport which is located in Chicago. When traveling from Chicago, it is helpful to have an alternative airport to fly into when you land in San Jose. Good options for arrival airports in San Jose, you can try San Francisco Airport (in San Francisco), Oakland Airport (in Oakland), or Monterey Regional Airport (in Monterey). The cheapest route from Chicago to San Jose is MDW — OAK with an average price of $161 RT during the month of June.
|Chicago O'Hare Intl Airport (ORD) to San Francisco Airport (SFO)||$254|
|Chicago O'Hare Intl Airport (ORD) to Oakland Airport (OAK)||$184|
|Chicago Midway Airport (MDW) to San Francisco Airport (SFO)||$204|
|Chicago O'Hare Intl Airport (ORD) to San Jose Airport (SJC)||$233|
|Chicago Midway Airport (MDW) to Oakland Airport (OAK)||$161|
|Chicago Midway Airport (MDW) to San Jose Airport (SJC)||$358|
|American Airlines||PriceFrom $128||Free Cancellation||Rating|
One of the stewards, and I wish I had asked his name but did not, had braids in his hair. He was African American and was just the most pleasant crew member I have experienced with your airline. He was professional but also personable. He had a great attitude and sense of humor. I know in your industry the public is quick to report the bad experiences, but this experience was great. If you can find out his name, please let him read this comment and let him know it was refreshing to have someone like him on the flight!
1 / 10
|Delta||PriceFrom $179||Free Cancellation||Rating|
It was so cold on the flight, otherwise okay.
1 / 10
|Alaska Airlines||PriceFrom $186||Free Cancellation||Rating|
Alaska is my favorite airline, for service, for cleanliness, for taking me places I need to go. Thank you for a wonderful first trip since COVID.
1 / 10
|United Airlines||PriceFrom $217||Free Cancellation||Rating|
First off....... In June 2022 Canada is still trying to flatten the curve. We had to wear masks for ~ 10 hours flying across the pond and listen to snarky comments from crew "cover your nose", while everyone went without a mask for the 1-2 hour plus meal service, absolutely ridiculous! I would recommend avoiding Canada until they understand that the world has moved on in the understanding of COVID-19 as an endemic virus. Second, all of the Air Canada flights were late or delayed due to low staffing. We were also left waiting on the tarmac for several hours due to problems with airport infrastructure, meaning-they could not find someone to extend the jetway to the plane, causing us to nearly miss our connection.... 45 minutes sitting 20 feet from the airport, major fail. Third, the Canadian officials were a bit cunty, I was very surprised, I traveled to Canada often prior to the pandemic and was always greeted with a smile and a laugh.... those days are over, or on hold while thy continue to battle the virus. On to the Middle East for more history. Cheers!
1 / 10
United Airlines flight deals from Chicago to San Jose start from $217 round-trip. Over the 4 United Airlines flights for this route in a normal week, average airfare is usually $517 round-trip - but some users have found much cheaper deals with momondo.
Some of our partner airlines flying from Chicago to San Jose are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are United Airlines, American Airlines, and Alaska Airlines. You can search for the full list of airlines like United Airlines that are offering this flexibility.
San Jose is 1836.7 mi away from Chicago. Flights usually cover this in 4h 33m, depending on flying conditions and air traffic around both airports.
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