Cheap flights from San Jose to Chicago from $100
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Jose to Chicago departing on 7/10. 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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Frontier flights from San Jose to Chicago Midway Airport
Our best Frontier deals on San Jose to Chicago Midway Airport flight tickets
Delta flights from San Jose to Chicago Midway Airport
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How to get the cheapest flight ticket from San Jose to Chicago Midway Airport
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 Chicago Midway Airport?
The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from San Jose, with most prices found around $388. If you are unable to visit Chicago Midway Airport during the month of November, then departing from San Jose during the month September is also very affordable. Most momondo users find prices during this month for around $400.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from San Jose. The lowest ticket price found for a Tuesday departure recently was $427. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from San Jose because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $546.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from San Jose in the evening is the least expensive time of day to depart. momondo users have found prices as low as $351 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $479. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest San Jose to Chicago Midway flight route?
Fly from San Jose to Chicago Midway for the best San Jose - Chicago Midway flight prices
What cabin class options are available on San Jose to Chicago Midway flights?
There are 1 cabin classes available to choose from on San Jose to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on San Jose to Chicago Midway Airport flights?
You could potentially save up to 41% on your flight if you consider stops on a San Jose to Chicago Midway Airport flight.
What is the cheapest airline that flies from San Jose to Chicago Midway?
Frontier, Delta, and Southwest are the most popular carriers operating from San Jose to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and United Airlines are the top three most popular airlines that fly to Chicago Midway Airport from San Jose according to our data. Southwest is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 6 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from San Jose to Chicago Midway Airport on average per day?
As of June 2025, there are 4 flights per day flying from San Jose to Chicago Midway Airport. The most common time of day flights depart is 6:00AM, with 61% of flights taking off at noon.
How many flights depart from San Jose to Chicago Midway Airport on average per week?
34 flights are operational weekly from San Jose to Chicago Midway Airport as of June 2025. The most popular departure day for this route is Tue, with 24% of flights per week taking off on this day.
When to book flights from San Jose to Chicago Midway Airport
Cheap San Jose to Chicago Midway Airport (SJC to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Jose to Chicago Midway Airport
How far is San Jose to Chicago Midway by plane?
Chicago Midway is 1830.8 mi away from San Jose. 4h 05m is a normal flight duration for this route.
When did momondo last update prices for flights from San Jose Airport to Chicago Midway Airport?
Prices for flights from San Jose Airport to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from San Jose Airport to Chicago Midway Airport?
As of June 2025, there are 3 operators available to choose from for flights from San Jose Airport to Chicago Midway Airport.
How old do you have to be to fly from San Jose Airport to Chicago Midway 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 San Jose Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from San Jose to Chicago Midway Airport?
Based on momondo bookings for flights between San Jose and Chicago Midway Airport, the leading plane model is Boeing 737 MAX 8, making up 24.11% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 13.45%, Airbus A320-100/200 with 11.28%, and Airbus A319 with 6.96%.
What is the most popular airline from San Jose to Chicago Midway Airport?
Based on momondo bookings for flights between San Jose and Chicago Midway Airport, the leading airline is Southwest, making up 77% of the total bookings. Other popular airlines include Frontier with 16% and United Airlines with 7%.
Best airlines flying from San Jose to Chicago Midway Airport
Compare and see reviews for airlines that fly from San Jose to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $132 | Free Cancellation | Rating 5.9 3,301 reviews | |||
| PriceFrom $287 | Free Cancellation | Rating 7.4 8,810 reviews | |||
| PriceFrom $358 | Free Cancellation | Rating 8.0 4,280 reviews |
Southwest Flights From San Jose to Chicago Midway Airport
Southwest is one of the most popular airlines flying from San Jose to Chicago Midway Airport, operating 34 flights/week on average for this route. A good Southwest flight deal for San Jose to Chicago Midway Airport starts from $358 round-trip, up to an average price of $487. Our users have rated Southwest at 8.0/10.
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Why should I use momondo to find a flight deal from San Jose to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from San Jose to Chicago for you.
Can I find flights from San Jose to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from San Jose on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from San Jose to Chicago?
Once all potential San Jose to Chicago 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 San Jose to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from San Jose are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.