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Cheap flights from San Jose to Chicago from $101

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 10/10. 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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Find the cheapest flights from San Jose to Chicago

Cheap round-trip flights

Logo
7:12 pm - 8:52 pmSJC-MDW
23h 40m1 stop
Logo
7:03 pm - 10:45 amMDW-SJC
17h 42m1 stop
$215
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Thu, Sep 25 - Mon, Sep 29
Logo
11:40 am - 8:52 pmSJC-MDW
7h 12m1 stop
Logo
7:03 pm - 10:45 amMDW-SJC
17h 42m1 stop
$250
Find Deal
Fri, Sep 26 - Mon, Sep 29
Logo
4:16 pm - 9:51 amSJC-MDW
15h 35m2 stops
Logo
7:03 pm - 10:45 amMDW-SJC
17h 42m1 stop
$259
Find Deal
Fri, Sep 26 - Mon, Sep 29
Delta Logo
10:30 pm - 9:48 amSJC-MDW
9h 18m1 stop
Delta Logo
12:43 pm - 7:49 pmMDW-SJC
9h 06m1 stop
$269Delta
Find Deal
Fri, Sep 26 - Tue, Sep 30
Delta Logo
10:25 pm - 9:40 amSJC-MDW
9h 15m1 stop
Delta Logo
9:20 am - 4:56 pmMDW-SJC
9h 36m2 stops
$274Delta
Find Deal
Mon, Oct 27 - Thu, Oct 30
Delta Logo
8:12 pm - 8:40 amSJC-MDW
10h 28m2 stops
Delta Logo
9:20 am - 6:14 pmMDW-SJC
10h 54m2 stops
$279Delta
Find Deal
Mon, Sep 22 - Wed, Sep 24
Logo
6:35 am - 9:58 pmSJC-MDW
13h 23m2 stops
Logo
6:20 am - 11:49 pmMDW-SJC
19h 29m2 stops
$282
Find Deal
Thu, Oct 2 - Mon, Oct 6
Southwest Logo
8:00 am - 2:05 pmSJC-MDW
4h 05mnonstop
Southwest Logo
7:55 pm - 10:25 pmMDW-SJC
4h 30mnonstop
$332Southwest
Find Deal
Mon, Sep 22 - Thu, Sep 25
Southwest Logo
6:35 am - 12:45 pmSJC-MDW
4h 10mnonstop
Southwest Logo
8:25 am - 10:55 amMDW-SJC
4h 30mnonstop
$333Southwest
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Wed, Sep 24 - Wed, Oct 1
Frontier Logo
12:27 pm - 12:37 pmSJC-MDW
22h 10m2 stops
Frontier Logo
12:30 pm - 11:32 amMDW-SJC
25h 02m1 stop
$357Frontier
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Fri, Nov 7 - Sun, Nov 9

Delta flights from San Jose to Chicago Midway Airport

Our best Delta deals on San Jose to Chicago Midway Airport flight tickets
Delta
Sep 26
SJC10:30 pmSan Jose
9h 18m
1 stop
MDW9:48 amChicago Midway
Sep 30
MDW12:43 pmChicago Midway
9h 06m
1 stop
SJC7:49 pmSan Jose
$269
Find similar
Delta
Oct 27
SJC10:25 pmSan Jose
9h 15m
1 stop
MDW9:40 amChicago Midway
Oct 30
MDW9:20 amChicago Midway
9h 36m
2 stops
SJC4:56 pmSan Jose
$274
Find similar
Delta
Sep 22
SJC8:12 pmSan Jose
10h 28m
2 stops
MDW8:40 amChicago Midway
Sep 24
MDW9:20 amChicago Midway
10h 54m
2 stops
SJC6:14 pmSan Jose
$279
Find similar

Southwest flights from San Jose to Chicago Midway Airport

Our best Southwest deals on San Jose to Chicago Midway Airport flight tickets
Southwest
Sep 22
SJC8:00 amSan Jose
4h 05m
MDW2:05 pmChicago Midway
Sep 25
MDW7:55 pmChicago Midway
4h 30m
SJC10:25 pmSan Jose
$332
Find similar
Southwest
Sep 24
SJC6:35 amSan Jose
4h 10m
MDW12:45 pmChicago Midway
Oct 1
MDW8:25 amChicago Midway
4h 30m
SJC10:55 amSan Jose
$333
Find similar
Southwest
Sep 17
SJC1:50 pmSan Jose
6h 50m
1 stop
MDW10:40 pmChicago Midway
Oct 1
MDW8:55 amChicago Midway
8h 10m
1 stop
SJC3:05 pmSan Jose
$342
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Jose 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 28, 2025.
Use the filters below to find and compare flights from San Jose to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 9/25

7:12 pm-8:52 pm

1 stop23h 40m

Chicago Midway

Mon 9/29

7:03 pm-10:45 am

1 stop17h 42m

$215

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 9/26

11:40 am-8:52 pm

1 stop7h 12m

Chicago Midway

Mon 9/29

7:03 pm-10:45 am

1 stop17h 42m

$250

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 9/26

4:16 pm-9:51 am

2 stops15h 35m

Chicago Midway

Mon 9/29

7:03 pm-10:45 am

1 stop17h 42m

$259

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 9/26

10:30 pm-9:48 am

1 stop9h 18m

Chicago Midway

Tue 9/30

12:43 pm-7:49 pm

1 stop9h 06m

$269

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 10/27

10:25 pm-9:40 am

1 stop9h 15m

Chicago Midway

Thu 10/30

9:20 am-4:56 pm

2 stops9h 36m

$274

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 9/22

8:12 pm-8:40 am

2 stops10h 28m

Chicago Midway

Wed 9/24

9:20 am-6:14 pm

2 stops10h 54m

$279

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Thu 10/2

6:35 am-9:58 pm

2 stops13h 23m

Chicago Midway

Mon 10/6

6:20 am-11:49 pm

2 stops19h 29m

$282

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 9/22

8:00 am-2:05 pm

Nonstop4h 05m

Chicago Midway

Thu 9/25

7:55 pm-10:25 pm

Nonstop4h 30m

$332

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 9/24

6:35 am-12:45 pm

Nonstop4h 10m

Chicago Midway

Wed 10/1

8:25 am-10:55 am

Nonstop4h 30m

$333

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Fri 11/7

12:27 pm-12:37 pm

2 stops22h 10m

Chicago Midway

Sun 11/9

12:30 pm-11:32 am

1 stop25h 02m

$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 Chicago from

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 $378. 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 $398.

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 $430. 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 $467. 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 is only 1 cabin class 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?

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

When to book flights from San Jose to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Jose 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 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

Best Price Found

$169

Fastest flight time

4h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Jose in the past 72 hours is $169. The best round-trip flight deal from San Jose to Chicago Midway Airport found on momondo in the last 72 hours is $322.
The fastest flight from San Jose to Chicago Midway Airport takes 4h 05m
Direct flights go from San Jose to Chicago Midway Airport every day.
Search flight deals

  • 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?

  • 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?

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

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
FrontierPriceFrom $128Free CancellationRating
5.8
3,204 reviews
Search Frontier flights
SouthwestPriceFrom $331Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • 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 25 flights/week on average for this route. A good Southwest flight deal for San Jose to Chicago Midway Airport starts from $331 round-trip, up to an average price of $489. 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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.

An easier way to manage your Chicago Midway Airport trip

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