What is the cheapest airline that flies from Chicago Midway to San Jose?

Frontier, Delta, and Southwest 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 84% of people opting to fly with this airline when traveling to San Jose. Keep in mind that there are 3 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 week?

As of August 2025, there are 13 flights per week flying from Chicago Midway Airport to San Jose. The most common day of the week flights depart is Mon, with 23% of flights taking off on this day.

How many flights depart from Chicago Midway Airport to San Jose on average per day?

1 flights are operational daily from Chicago Midway Airport to San Jose as of August 2025. The most popular departure time for this route is 7:00PM, with 50% of flights per day taking off at noon.

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 August 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.

$87 Cheap Flights from Chicago Midway Airport to San Jose in 2025

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Find the cheapest flights from Chicago Midway Airport to San Jose

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:24 pm - 11:32 amMDW-SJC

19h 08m1 stop

12:27 pm - 12:24 amSJC-MDW

9h 57m1 stop

$203Frontier

Find Deal

Thu, Oct 9 - Fri, Oct 17

7:03 pm - 10:45 amMDW-SJC

17h 42m1 stop

6:35 am - 9:58 pmSJC-MDW

13h 23m2 stops

$209

Find Deal

Mon, Sep 29 - Thu, Oct 2

1:43 pm - 8:44 pmMDW-SJC

9h 01m1 stop

10:25 pm - 9:40 amSJC-MDW

9h 15m1 stop

$269Delta

Find Deal

Thu, Oct 2 - Mon, Oct 6

1:43 pm - 8:44 pmMDW-SJC

9h 01m1 stop

8:10 pm - 8:40 amSJC-MDW

10h 30m2 stops

$274Delta

Find Deal

Thu, Oct 2 - Mon, Oct 6

1:08 pm - 10:55 pmMDW-SJC

11h 47m2 stops

8:12 pm - 8:40 amSJC-MDW

10h 28m2 stops

$279Delta

Find Deal

Tue, Sep 16 - Tue, Sep 23

4:48 pm - 10:45 amMDW-SJC

19h 57m2 stops

2:14 pm - 3:53 pmSJC-MDW

23h 39m1 stop

$290

Find Deal

Mon, Sep 8 - Thu, Sep 11

5:04 pm - 10:58 pmMDW-SJC

7h 54m1 stop

12:40 pm - 10:14 pmSJC-MDW

7h 34m1 stop

$311Delta

Find Deal

Wed, Oct 15 - Tue, Oct 21

5:25 pm - 7:55 pmMDW-SJC

4h 30mnonstop

8:35 pm - 5:15 amSJC-MDW

6h 40m1 stop

$332Southwest

Find Deal

Wed, Oct 8 - Wed, Oct 15

5:40 pm - 8:10 pmMDW-SJC

4h 30mnonstop

6:35 am - 12:45 pmSJC-MDW

4h 10mnonstop

$333Southwest

Find Deal

Tue, Sep 16 - Tue, Sep 23

10:13 am - 11:30 amMDW-SJC

27h 17m2 stops

12:26 pm - 3:53 pmSJC-MDW

25h 27m1 stop

$381Frontier

Find Deal

Thu, Sep 25 - Sun, Sep 28

Delta flights from Chicago Midway Airport to San Jose

Our best Delta deals on Chicago Midway Airport to San Jose flight tickets

Delta

Oct 2

MDW1:43 pmChicago Midway

9h 01m

1 stop

SJC8:44 pmSan Jose

Oct 6

SJC10:25 pmSan Jose

9h 15m

1 stop

MDW9:40 amChicago Midway

$269

Find similar

Delta

Oct 2

MDW1:43 pmChicago Midway

9h 01m

1 stop

SJC8:44 pmSan Jose

Oct 6

SJC8:10 pmSan Jose

10h 30m

2 stops

MDW8:40 amChicago Midway

$274

Find similar

Delta

Sep 16

MDW1:08 pmChicago Midway

11h 47m

2 stops

SJC10:55 pmSan Jose

Sep 23

SJC8:12 pmSan Jose

10h 28m

2 stops

MDW8:40 amChicago Midway

$279

Find similar

Frontier flights from Chicago Midway Airport to San Jose

Our best Frontier deals on Chicago Midway Airport to San Jose flight tickets

Frontier

Oct 9

MDW6:24 pmChicago Midway

19h 08m

1 stop

SJC11:32 amSan Jose

Oct 17

SJC12:27 pmSan Jose

9h 57m

1 stop

MDW12:24 amChicago Midway

$203

Find similar

Frontier

Sep 25

MDW10:13 amChicago Midway

27h 17m

2 stops

SJC11:30 amSan Jose

Sep 28

SJC12:26 pmSan Jose

25h 27m

1 stop

MDW3:53 pmChicago Midway

$381

Find similar

Frontier

Sep 3

MDW9:00 pmChicago Midway

18h 14m

2 stops

SJC1:14 pmSan Jose

Sep 14

SJC12:26 pmSan Jose

16h 45m

2 stops

MDW7:11 amChicago Midway

$467

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to San Jose that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 10/9

6:24 pm-11:32 am

1 stop19h 08m

San Jose

Fri 10/17

12:27 pm-12:24 am

1 stop9h 57m

$203

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 9/29

7:03 pm-10:45 am

1 stop17h 42m

San Jose

Thu 10/2

6:35 am-9:58 pm

2 stops13h 23m

$209

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 10/2

1:43 pm-8:44 pm

1 stop9h 01m

San Jose

Mon 10/6

10:25 pm-9:40 am

1 stop9h 15m

$269

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 10/2

1:43 pm-8:44 pm

1 stop9h 01m

San Jose

Mon 10/6

8:10 pm-8:40 am

2 stops10h 30m

$274

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 9/16

1:08 pm-10:55 pm

2 stops11h 47m

San Jose

Tue 9/23

8:12 pm-8:40 am

2 stops10h 28m

$279

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Mon 9/8

4:48 pm-10:45 am

2 stops19h 57m

San Jose

Thu 9/11

2:14 pm-3:53 pm

1 stop23h 39m

$290

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 10/15

5:04 pm-10:58 pm

1 stop7h 54m

San Jose

Tue 10/21

12:40 pm-10:14 pm

1 stop7h 34m

$311

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Wed 10/8

5:25 pm-7:55 pm

Nonstop4h 30m

San Jose

Wed 10/15

8:35 pm-5:15 am

1 stop6h 40m

$332

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Tue 9/16

5:40 pm-8:10 pm

Nonstop4h 30m

San Jose

Tue 9/23

6:35 am-12:45 pm

Nonstop4h 10m

$333

ChicagoSan Jose

MDW - SJC

MDWSJC

Chicago Midway

Thu 9/25

10:13 am-11:30 am

2 stops27h 17m

San Jose

Sun 9/28

12:26 pm-3:53 pm

1 stop25h 27m

$381

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to San Jose?

In general, January 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 $378. If you aren’t able to travel to San Jose during the month of January, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $382.

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 Wednesday when prices can be found for as low as $444. 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 $582.

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 $440. In contrast, the most expensive time of day to depart to San Jose is in the evening when prices are around $521.

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 cabin class options are available on Chicago Midway to San Jose flights?

There is only 1 cabin class available to choose from on Chicago Midway to San Jose 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 Chicago Midway Airport to San Jose flights?

You could potentially save up to 20% on your flight if you consider stops on a Chicago Midway Airport to San Jose flight.

When to book flights from Chicago Midway Airport to San Jose

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San Jose according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

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

Best Price Found	$182
Fastest flight time	4h 30m
Direct flights	Every day
Airports in San Jose	1 airport

The best one-way flight to San Jose from Chicago Midway Airport in the past 72 hours is $182. The best round-trip flight deal from Chicago Midway Airport to San Jose found on momondo in the last 72 hours is $343.

The fastest flight from Chicago Midway Airport to San Jose takes 4h 30m

Direct flights go from Chicago Midway Airport to San Jose every day.

There is 1 airport near San Jose: San Jose (SJC)

Search flight deals

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 August 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 37.17% of the total bookings. Other popular models include Airbus A320-100/200 with 14.66%, Boeing 737 MAX 9 with 6.28%, and Boeing 737-800 with 5.76%.
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 86% of all bookings. The subsequent popular airline is Frontier at 14%.

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
Frontier	PriceFrom $138	Free Cancellation	Rating 5.8 3,202 reviews		Search Frontier flights
Southwest	PriceFrom $365	Free Cancellation	Rating 8.0 4,241 reviews		Search Southwest flights

Southwest Flights From Chicago Midway Airport to San Jose
Across 13 Southwest flights from Chicago Midway Airport to San Jose this week, the average price was $461, with the best Southwest deals starting from $365 round-trip. 4,241 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.

An easier way to manage your San Jose trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Chicago Midway Airport to San Jose from $87

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Find the cheapest 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

Frontier flights from Chicago Midway Airport to San Jose

Our best Frontier deals on Chicago Midway Airport to San Jose flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to San Jose that are best for you.

See travel insights to San Jose from

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?

What is the cheapest day to depart on your flight to San Jose?

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 $440. In contrast, the most expensive time of day to depart to San Jose is in the evening when prices are around $521.

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 cabin class options are available on Chicago Midway to San Jose flights?

There is only 1 cabin class available to choose from on Chicago Midway to San Jose 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 Chicago Midway Airport to San Jose flights?

You could potentially save up to 20% on your flight if you consider stops on a Chicago Midway Airport to San Jose flight.

What is the cheapest airline that flies from Chicago Midway to San Jose?

Frontier, Delta, and Southwest are the most popular carriers operating from Chicago Midway to San Jose

What airlines fly to San Jose?

How many flights depart from Chicago Midway Airport to San Jose on average per day?

1 flights are operational daily from Chicago Midway Airport to San Jose as of August 2025. The most popular departure time for this route is 7:00PM, with 50% 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 August 2025, there are 13 flights per week flying from Chicago Midway Airport to San Jose. The most common day of the week flights depart is Mon, with 23% 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

Best Price Found

Fastest flight time

Direct flights

Airports in San Jose

How far is Chicago Midway to San Jose by plane?

When did momondo last update prices for flights from Chicago Midway Airport to San Jose Airport?

How many operators does momondo search 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?

What documentation or ID do you need to fly to San Jose Airport?

What is the most popular plane model from Chicago Midway Airport to San Jose?

What is the most popular airline from Chicago Midway Airport to San Jose?

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

Southwest Flights From Chicago Midway Airport to San Jose

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Jose?

Can I find flights from Chicago to San Jose with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to San Jose?

I’m not ready to book a flight from Chicago to San Jose right now. Can momondo alert me if prices change?

An easier way to manage your San Jose trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing California