Cheap flights from Chicago Midway Airport to San Jose from $120
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Jose departing on 6/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Southwest flights from Chicago Midway Airport to San Jose
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Delta flights from Chicago Midway Airport to San Jose
Our best Delta deals on Chicago Midway Airport to San Jose flight tickets
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How to get the cheapest flight ticket from Chicago Midway Airport to San Jose
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to San Jose?
In general, November is the cheapest month to fly from Chicago Midway Airport to San Jose. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $357. If you aren’t able to travel to San Jose during the month of November, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $378.
What is the cheapest day to depart on your flight to San Jose?
The cheapest day to depart on your flight to San Jose is on a Thursday when prices can be found for as low as $453. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to San Jose on Sunday is $583.
What is the cheapest time of day to depart on your flight to San Jose?
Our most recent data shows that the best time of day to fly to San Jose is in the afternoon. Flights from Chicago Midway Airport to San Jose during this time can be as low as $443. In contrast, the most expensive time of day to depart to San Jose is in the morning when prices are around $513.
What is the cheapest Chicago Midway to San Jose flight route?
Fly from Chicago Midway to San Jose for the best Chicago Midway - San Jose flight prices
What is the cheapest airline that flies from Chicago Midway to San Jose?
Frontier, Southwest, and Delta are the most popular carriers operating from Chicago Midway to San Jose
What airlines fly to San Jose?
Southwest, Frontier and United Airlines are the top three most popular airlines that fly to San Jose from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 62% of people opting to fly with this airline when traveling to San Jose. Keep in mind that there are 4 different airlines that fly to San Jose on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to San Jose on average per day?
2 flights are operational daily from Chicago Midway Airport to San Jose as of May 2025. The most popular departure time for this route is 8:00AM, with 72% of flights per day taking off at noon.
How many flights depart from Chicago Midway Airport to San Jose on average per week?
As of May 2025, there are 19 flights per week flying from Chicago Midway Airport to San Jose. The most common day of the week flights depart is Mon, with 26% of flights taking off on this day.
When to book flights from Chicago Midway Airport to San Jose
Cheap Chicago Midway Airport to San Jose (MDW to SJC) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Jose
How far is Chicago Midway to San Jose by plane?
A flight from Chicago Midway to San Jose will travel around 1830.8 mi. A reasonable flight in good conditions will take 4h 30m.
When did momondo last update prices for flights from Chicago Midway Airport to San Jose Airport?
Prices for flights from Chicago Midway Airport to San Jose Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to San Jose Airport?
As of May 2025, there are 2 operators available to choose from for flights from Chicago Midway Airport to San Jose Airport.
How old do you have to be to fly from Chicago Midway Airport to San Jose Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San Jose Airport.
What documentation or ID do you need to fly to San Jose Airport?
The travel and health documents you'll need for your trip to San Jose Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Jose Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to San Jose?
Based on momondo bookings for flights between Chicago Midway Airport and San Jose, the leading plane model is Boeing 737 MAX 8, making up 25.34% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 9.19%, Airbus A319 with 8.74%, and Airbus A320-100/200 with 7.17%.
What is the most popular airline from Chicago Midway Airport to San Jose?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to San Jose is Southwest, representing 80% of all bookings. The subsequent popular airline is Frontier at 20%.
Best airlines flying from Chicago Midway Airport to San Jose
Compare and see reviews for airlines that fly from Chicago Midway Airport to San Jose with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $138 | Free Cancellation | Rating 5.9 3,289 reviews | |||
| PriceFrom $376 | Free Cancellation | Rating 8.0 4,292 reviews |
Southwest Flights From Chicago Midway Airport to San Jose
Across 19 Southwest flights from Chicago Midway Airport to San Jose this week, the average price was $459, with the best Southwest deals starting from $376 round-trip. 4,292 users have rated Southwest on momondo, with an average score of 8.0/10.
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to San Jose?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San Jose. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to San Jose with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to San Jose flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to San Jose?
Once all potential Chicago to San Jose flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to San Jose right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to San Jose flights. All you need is a valid email address and we will do the rest; it is that quick and easy.