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Cheap flights from Chicago Midway Airport to San Jose from $141

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to San Jose

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:10 pm - 9:45 pmMDW  Chicago Midway-SJC San Jose
4h 35mnonstop
Southwest Logo
6:40 am - 12:40 pmSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
$287Southwest
Sat, Oct 24 - Sat, Oct 31
Southwest Logo
10:10 am - 12:55 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
Southwest Logo
8:30 am - 2:35 pmSJC  San Jose-MDW Chicago Midway
4h 05mnonstop
$287Southwest
Wed, Nov 4 - Sat, Nov 7
Southwest Logo
3:50 pm - 6:30 pmMDW  Chicago Midway-SJC San Jose
4h 40mnonstop
Southwest Logo
8:30 am - 2:35 pmSJC  San Jose-MDW Chicago Midway
4h 05mnonstop
$287Southwest
Wed, Nov 4 - Sat, Nov 7
Southwest Logo
10:15 am - 1:05 pmMDW  Chicago Midway-SJC San Jose
4h 50mnonstop
Southwest Logo
6:25 am - 12:30 pmSJC  San Jose-MDW Chicago Midway
4h 05mnonstop
$287Southwest
Wed, Jan 6 - Tue, Jan 12
Southwest Logo
10:15 am - 1:05 pmMDW  Chicago Midway-SJC San Jose
4h 50mnonstop
Southwest Logo
6:25 am - 12:30 pmSJC  San Jose-MDW Chicago Midway
4h 05mnonstop
$287Southwest
Wed, Jan 6 - Wed, Jan 13
Southwest Logo
8:00 pm - 10:45 pmMDW  Chicago Midway-SJC San Jose
4h 45mnonstop
Southwest Logo
7:50 am - 4:40 pmSJC  San Jose-MDW Chicago Midway
6h 50m1 stop Seattle/Tacoma Intl
$292Southwest
Wed, Jan 6 - Tue, Jan 12
Delta Logo
6:04 am - 11:44 amMDW  Chicago Midway-SJC San Jose
7h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:20 am - 4:47 pmSJC  San Jose-MDW Chicago Midway
8h 27m1 stop Minneapolis St Paul
$357Delta
Tue, Oct 20 - Mon, Oct 26
Delta Logo
6:04 am - 11:44 amMDW  Chicago Midway-SJC San Jose
7h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:45 pm - 10:03 amSJC  San Jose-MDW Chicago Midway
9h 18m1 stop Atlanta Hartsfield-Jackson
$357Delta
Tue, Oct 20 - Mon, Oct 26
Delta Logo
6:00 am - 11:56 amMDW  Chicago Midway-SJC San Jose
7h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:45 pm - 10:10 pmSJC  San Jose-MDW Chicago Midway
7h 25m1 stop Atlanta Hartsfield-Jackson
$357Delta
Thu, Jan 21 - Mon, Jan 25
Delta Logo
6:00 am - 11:50 amMDW  Chicago Midway-SJC San Jose
7h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 4:50 pmSJC  San Jose-MDW Chicago Midway
8h 45m1 stop Minneapolis St Paul
$357Delta
Wed, Nov 18 - Tue, Dec 1

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Southwest flights from Chicago Midway Airport to San Jose, California

Our best Southwest deals on Chicago Midway Airport to San Jose, California flight tickets
Southwest
Oct 24
MDW7:10 pmChicago Midway
4h 35m
SJC9:45 pmSan Jose
Oct 31
SJC6:40 amSan Jose
4h 00m
MDW12:40 pmChicago Midway
$287
Southwest
Oct 24
MDW12:50 pmChicago Midway
4h 35m
SJC3:25 pmSan Jose
Oct 31
SJC6:15 amSan Jose
8h 30m
1 stop
MDW4:45 pmChicago Midway
$297
Southwest
Oct 24
MDW7:10 pmChicago Midway
4h 35m
SJC9:45 pmSan Jose
Oct 31
SJC6:30 amSan Jose
8h 20m
2 stops
MDW4:50 pmChicago Midway
$302

Delta flights from Chicago Midway Airport to San Jose, California

Our best Delta deals on Chicago Midway Airport to San Jose, California flight tickets
Delta
Oct 20
MDW6:04 amChicago Midway
7h 40m
1 stop
SJC11:44 amSan Jose
Oct 26
SJC10:45 pmSan Jose
9h 18m
1 stop
MDW10:03 amChicago Midway
$357
Delta
Oct 17
MDW10:12 amChicago Midway
9h 41m
1 stop
SJC5:53 pmSan Jose
Oct 20
SJC8:32 pmSan Jose
10h 12m
2 stops
MDW8:44 amChicago Midway
$362
Delta
Oct 20
MDW1:27 pmChicago Midway
10h 41m
2 stops
SJC10:08 pmSan Jose
Oct 26
SJC8:32 pmSan Jose
10h 12m
2 stops
MDW8:44 amChicago Midway
$368

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Sat 10/24

7:10 pm-9:45 pm

Nonstop4h 35m

San Jose

Sat 10/31

6:40 am-12:40 pm

Nonstop4h 00m

$287

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Wed 11/4

10:10 am-12:55 pm

Nonstop4h 45m

San Jose

Sat 11/7

8:30 am-2:35 pm

Nonstop4h 05m

$287

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Wed 11/4

3:50 pm-6:30 pm

Nonstop4h 40m

San Jose

Sat 11/7

8:30 am-2:35 pm

Nonstop4h 05m

$287

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Wed 1/6

10:15 am-1:05 pm

Nonstop4h 50m

San Jose

Tue 1/12

6:25 am-12:30 pm

Nonstop4h 05m

$287

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Wed 1/6

10:15 am-1:05 pm

Nonstop4h 50m

San Jose

Wed 1/13

6:25 am-12:30 pm

Nonstop4h 05m

$287

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Wed 1/6

8:00 pm-10:45 pm

Nonstop4h 45m

San Jose

Tue 1/12

7:50 am-4:40 pm

1 stop6h 50m

$292

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Tue 10/20

6:04 am-11:44 am

1 stop7h 40m

San Jose

Mon 10/26

6:20 am-4:47 pm

1 stop8h 27m

$357

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Tue 10/20

6:04 am-11:44 am

1 stop7h 40m

San Jose

Mon 10/26

10:45 pm-10:03 am

1 stop9h 18m

$357

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Thu 1/21

6:00 am-11:56 am

1 stop7h 56m

San Jose

Mon 1/25

12:45 pm-10:10 pm

1 stop7h 25m

$357

ChicagoSan Jose

MDW Chicago Midway - SJC San Jose

MDWSJC

Chicago Midway

Wed 11/18

6:00 am-11:50 am

1 stop7h 50m

San Jose

Tue 12/1

6:05 am-4:50 pm

1 stop8h 45m

$357

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San Jose from

How to get the cheapest flight ticket from Chicago Midway Airport to San Jose, California

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 typical price of a round-trip flight between Chicago Midway Airport and San Jose, California?

Prices are currently low for flights on this route.

Typical prices usually range from $346 to $425.
The lowest price recently found on this route was $287.

What is the cheapest month to fly to San Jose, California?

The month of February is, on average, the cheapest month to fly to San Jose, California from Chicago Midway Airport, with most prices found around $0. If you are unable to visit San Jose, California during the month of February, then departing from Chicago Midway Airport during the month April is also very affordable. Most momondo users find prices during this month for around $285.

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

On average, the least expensive day to fly to San Jose, California from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $407. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to San Jose, California for around $778.

What is the cheapest time of day to depart on your flight to San Jose, California?

The cheapest time of day to fly to San Jose, California is at noon when flights can be purchased for as low as $385. In the evening is when there is more demand to fly to San Jose, California, so prices are often more expensive at around $488 per ticket.

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 Airport to San Jose, California flights?

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

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to San Jose, California.

When to book flights from Chicago Midway Airport to San Jose, California

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San Jose, California 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, California (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, California

Best Price Found

$141

Fastest flight time

4h 35m

Direct flights

Every day

Airports in San Jose, California

1 airport
The best one-way flight to San Jose, California from Chicago Midway Airport in the past 72 hours is $141. The best round-trip flight deal from Chicago Midway Airport to San Jose, California found on momondo in the last 72 hours is $287.
The fastest flight from Chicago Midway Airport to San Jose, California takes 4h 35m
Direct flights go from Chicago Midway Airport to San Jose, California every day.
There is 1 airport in San Jose, California. From Chicago Midway Airport there are direct flights to San Jose (SJC).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San Jose, California

  • 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 35m.

  • 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?

  • 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, California?

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

Best airlines flying from Chicago Midway Airport to San Jose, California

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Jose, California with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $298Free CancellationRating
8.0
4,196 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Jose, California

    Across 12 Southwest flights from Chicago Midway Airport to San Jose, California this week, the average price was $488, with the best Southwest deals starting from $298 round-trip. 4,196 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.

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