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Cheap flights from San Jose, California to Chicago from $169

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, California to Chicago departing on 9/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from San Jose, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:40 pm - 10:36 pmSJC  San Jose-MDW Chicago Midway
7h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:59 am - 5:34 pmMDW  Chicago Midway-SJC San Jose
9h 35m1 stop Minneapolis St Paul
$314Delta
Tue, Sep 1 - Sat, Sep 5
Southwest Logo
7:35 pm - 5:05 amSJC  San Jose-MDW Chicago Midway
7h 30m1 stop Seattle/Tacoma Intl
Southwest Logo
6:15 am - 10:30 amMDW  Chicago Midway-SJC San Jose
6h 15m1 stop San Diego
$315Southwest
Thu, Sep 17 - Thu, Sep 24
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
10:40 am - 6:05 pmMDW  Chicago Midway-SJC San Jose
9h 25m2 stops Dallas Love Field Los Angeles
$315Southwest
Mon, Sep 28 - Sat, Oct 3
Southwest Logo
6:25 am - 4:05 pmSJC  San Jose-MDW Chicago Midway
7h 40m2 stops Denver Intl Wichita Eisenhower National
Southwest Logo
6:05 am - 11:45 amMDW  Chicago Midway-SJC San Jose
7h 40m1 stop Denver Intl
$316Southwest
Wed, Oct 21 - Thu, Oct 22
Southwest Logo
11:55 am - 5:55 pmSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
9:15 pm - 11:55 pmMDW  Chicago Midway-SJC San Jose
4h 40mnonstop
$316Southwest
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
8:20 pm - 5:50 amSJC  San Jose-MDW Chicago Midway
7h 30m1 stop Phoenix Sky Harbor Intl
Southwest Logo
6:15 am - 10:30 amMDW  Chicago Midway-SJC San Jose
6h 15m1 stop San Diego
$317Southwest
Mon, Sep 14 - Fri, Sep 18
Southwest Logo
11:55 am - 5:55 pmSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
5:20 pm - 10:30 pmMDW  Chicago Midway-SJC San Jose
7h 10m2 stops Omaha Eppley Airfield Denver Intl
$318Southwest
Fri, Nov 6 - Mon, Nov 9
Delta Logo
1:00 pm - 10:56 pmSJC  San Jose-MDW Chicago Midway
7h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 10:08 pmMDW  Chicago Midway-SJC San Jose
11h 08m1 stop Atlanta Hartsfield-Jackson
$320Delta
Thu, Nov 12 - Mon, Nov 16
Delta Logo
10:50 pm - 10:03 amSJC  San Jose-MDW Chicago Midway
9h 13m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:45 pm - 9:25 pmMDW  Chicago Midway-SJC San Jose
10h 40m1 stop Atlanta Hartsfield-Jackson
$320Delta
Mon, Oct 5 - Thu, Oct 8
Southwest Logo
11:00 pm - 5:00 amSJC  San Jose-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
8:30 pm - 11:00 pmMDW  Chicago Midway-SJC San Jose
4h 30mnonstop
$320Southwest
Tue, Sep 1 - Wed, Sep 2

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Southwest flights from San Jose, California to Chicago Midway Airport

Our best Southwest deals on San Jose, California to Chicago Midway Airport flight tickets
Southwest
Sep 17
SJC7:35 pmSan Jose
7h 30m
1 stop
MDW5:05 amChicago Midway
Sep 24
MDW6:15 amChicago Midway
6h 15m
1 stop
SJC10:30 amSan Jose
$315
Southwest
Oct 21
SJC6:25 amSan Jose
7h 40m
2 stops
MDW4:05 pmChicago Midway
Oct 22
MDW6:05 amChicago Midway
7h 40m
1 stop
SJC11:45 amSan Jose
$316
Southwest
Sep 14
SJC8:20 pmSan Jose
7h 30m
1 stop
MDW5:50 amChicago Midway
Sep 18
MDW6:15 amChicago Midway
6h 15m
1 stop
SJC10:30 amSan Jose
$317

Delta flights from San Jose, California to Chicago Midway Airport

Our best Delta deals on San Jose, California to Chicago Midway Airport flight tickets
Delta
Sep 1
SJC12:40 pmSan Jose
7h 56m
1 stop
MDW10:36 pmChicago Midway
Sep 5
MDW9:59 amChicago Midway
9h 35m
1 stop
SJC5:34 pmSan Jose
$314
Delta
Nov 12
SJC1:00 pmSan Jose
7h 56m
1 stop
MDW10:56 pmChicago Midway
Nov 16
MDW1:00 pmChicago Midway
11h 08m
1 stop
SJC10:08 pmSan Jose
$323
Delta
Sep 8
SJC12:51 pmSan Jose
7h 53m
1 stop
MDW10:44 pmChicago Midway
Sep 11
MDW9:59 amChicago Midway
9h 47m
1 stop
SJC5:46 pmSan Jose
$324

momondo Fare Finder

 
Customize your flight search to find flights from San Jose, California to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 15, 2026.
Use the filters below to find and compare flights from San Jose, California to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Tue 9/1

12:40 pm-10:36 pm

1 stop7h 56m

Chicago Midway

Sat 9/5

9:59 am-5:34 pm

1 stop9h 35m

$314

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Thu 9/17

7:35 pm-5:05 am

1 stop7h 30m

Chicago Midway

Thu 9/24

6:15 am-10:30 am

1 stop6h 15m

$315

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Mon 9/28

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Sat 10/3

10:40 am-6:05 pm

2 stops9h 25m

$315

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Wed 10/21

6:25 am-4:05 pm

2 stops7h 40m

Chicago Midway

Thu 10/22

6:05 am-11:45 am

1 stop7h 40m

$316

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Thu 11/5

11:55 am-5:55 pm

Nonstop4h 00m

Chicago Midway

Mon 11/9

9:15 pm-11:55 pm

Nonstop4h 40m

$316

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Mon 9/14

8:20 pm-5:50 am

1 stop7h 30m

Chicago Midway

Fri 9/18

6:15 am-10:30 am

1 stop6h 15m

$317

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Fri 11/6

11:55 am-5:55 pm

Nonstop4h 00m

Chicago Midway

Mon 11/9

5:20 pm-10:30 pm

2 stops7h 10m

$318

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Thu 11/12

1:00 pm-10:56 pm

1 stop7h 56m

Chicago Midway

Mon 11/16

1:00 pm-10:08 pm

1 stop11h 08m

$320

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Mon 10/5

10:50 pm-10:03 am

1 stop9h 13m

Chicago Midway

Thu 10/8

12:45 pm-9:25 pm

1 stop10h 40m

$320
Quickest round-trip

San JoseChicago

SJC San Jose - MDW Chicago Midway

SJCMDW

San Jose

Tue 9/1

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Wed 9/2

8:30 pm-11:00 pm

Nonstop4h 30m

$320

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 Chicago from

How to get the cheapest flight ticket from San Jose, California 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 typical price of a round-trip flight between San Jose, California and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $407 to $440.
The lowest price recently found on this route was $314.

What is the cheapest month to fly to Chicago Midway Airport?

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from San Jose, California, with most prices found around $393. If you are unable to visit Chicago Midway Airport during the month of October, then departing from San Jose, California during the month August is also very affordable. Most momondo users find prices during this month for around $407.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from San Jose, California. The lowest ticket price found for a Saturday departure recently was $447. 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, California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $677.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San Jose, California in the evening is the least expensive time of day to depart. momondo users have found prices as low as $482 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $531. 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, California to Chicago Midway Airport flights?

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

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

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

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

Cheap San Jose, California 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, California to Chicago Midway Airport

Best Price Found

$196

Fastest flight time

4h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Jose, California in the past 72 hours is $196. The best round-trip flight deal from San Jose, California to Chicago Midway Airport found on momondo in the last 72 hours is $387.
The fastest flight from San Jose, California to Chicago Midway Airport takes 4h 00m
Direct flights go from San Jose, California to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from San Jose, California 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 00m 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?

  • 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, California to Chicago Midway Airport?

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

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

Compare and see reviews for airlines that fly from San Jose, California to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $310Free CancellationRating
8.0
4,220 reviews
Search Southwest flights

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

    Southwest is one of the most popular airlines flying from San Jose, California to Chicago Midway Airport, operating 10 flights/week on average for this route. A good Southwest flight deal for San Jose, California to Chicago Midway Airport starts from $310 round-trip, up to an average price of $541. Our users have rated Southwest at 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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.

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