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Cheap flights from Chicago Midway Airport to San Jose from $61

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Jose departing on 2/12. 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 Chicago Midway Airport to San Jose

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to San Jose that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to San Jose.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to San Jose? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San Jose, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to San Jose

Find recent round-trip train or bus tickets from Chicago Midway Airport to San Jose.

All round-trip flight deals to San Jose

The cheapest plane tickets to San Jose found on KAYAK recently.
7:15 am - 12:11 pmMDW-SJC
6h 56m1 stop
4:03 pm - 12:17 amSJC-MDW
6h 14m1 stop
$126Frontier
Find Deal
Mon, Feb 10 - Wed, Feb 12
7:15 am - 12:11 pmMDW-SJC
6h 56m1 stop
1:11 pm - 12:17 amSJC-MDW
9h 06m1 stop
$128Frontier
Find Deal
Mon, Jan 20 - Thu, Jan 23
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
5:19 pm - 11:44 amSJC-MDW
16h 25m1 stop
$138Frontier
Find Deal
Mon, Dec 16 - Sat, Jan 25
7:15 am - 12:08 pmMDW-SJC
6h 53m1 stop
1:20 pm - 9:32 pmSJC-MDW
6h 12m1 stop
$146Frontier
Find Deal
Mon, Dec 16 - Wed, Dec 18
10:44 am - 9:35 amMDW-SJC
24h 51m2 stops
5:19 pm - 8:14 pmSJC-MDW
24h 55m2 stops
Sun, Jan 5 - Sun, Jan 12
2:15 pm - 9:07 pmMDW-SJC
8h 52m1 stop
6:15 am - 5:11 pmSJC-MDW
8h 56m1 stop
$326Delta
Find Deal
Wed, Dec 18 - Wed, Dec 25
11:19 am - 8:51 pmMDW-SJC
11h 32m2 stops
6:20 am - 5:47 pmSJC-MDW
9h 27m1 stop
$331Delta
Find Deal
Sat, Feb 8 - Sat, Feb 15
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
$371Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
8:00 am - 2:05 pmSJC-MDW
4h 05mnonstop
$374Southwest
Find Deal
Thu, Jan 23 - Sat, Feb 1
8:41 pm - 6:26 pmMDW-SJC
23h 45m2 stops
6:15 am - 10:24 pmSJC-MDW
14h 09m2 stops
Sun, Jan 5 - Sun, Jan 12
7:05 am - 3:03 pmMDW-SJC
9h 58m1 stop
$61Frontier
Find Deal
Wed, Feb 12
7:15 am - 12:11 pmMDW-SJC
6h 56m1 stop
$63Frontier
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Thu, Jan 23
4:58 pm - 11:06 pmMDW-SJC
8h 08m1 stop
$163Delta
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Sat, Dec 14
6:00 am - 5:24 pmMDW-SJC
13h 24m2 stops
$168Delta
Find Deal
Tue, Dec 17
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
$187Southwest
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Tue, Jan 7
6:05 am - 10:45 amMDW-SJC
6h 40m1 stop
$196Southwest
Find Deal
Sat, Jan 11
6:31 pm - 11:21 pmMDW-SJC
30h 50m3 stops
Sun, Jan 5
6:31 pm - 7:46 amMDW-SJC
39h 15m3 stops
Thu, Jan 2
11:00 am - 11:33 amMDW-SJC
26h 33m3 stops
$388Volaris
Find Deal
Fri, Mar 7
10:41 pm - 9:02 amMDW-SJC
36h 21m3 stops
$393Volaris
Find Deal
Mon, Mar 10
9:40 pm - 7:52 amMDW-SJC
12h 12m1 stop
9:17 am - 7:50 pmSJC-MDW
8h 33m1 stop
$218Frontier
Find Deal
Sat, Nov 23 - Tue, Nov 26
9:40 pm - 7:52 amMDW-SJC
12h 12m1 stop
9:17 am - 7:50 pmSJC-MDW
8h 33m1 stop
$368Frontier
Find Deal
Sat, Nov 23 - Tue, Nov 26
9:40 pm - 7:52 amMDW-SJC
12h 12m1 stop
1:41 pm - 1:10 pmSJC-MDW
21h 29m1 stop
$376Frontier
Find Deal
Sat, Nov 23 - Thu, Nov 28
9:40 pm - 7:52 amMDW-SJC
12h 12m1 stop
10:42 am - 1:40 pmSJC-MDW
24h 58m1 stop
$653Frontier
Find Deal
Sat, Nov 23 - Sun, Nov 24
2:17 pm - 8:49 pmMDW-SJC
8h 32m1 stop
6:40 am - 5:54 pmSJC-MDW
9h 14m1 stop
$985Delta
Find Deal
Tue, Nov 26 - Mon, Dec 2
9:31 am - 6:18 pmMDW-SJC
10h 47m2 stops
12:30 pm - 9:46 pmSJC-MDW
7h 16m1 stop
$990Delta
Find Deal
Tue, Nov 26 - Mon, Dec 2
10:41 am - 8:13 pmMDW-SJC
11h 32m2 stops
6:58 pm - 8:51 amSJC-MDW
11h 53m2 stops
$1,094Delta
Find Deal
Sat, Nov 23 - Tue, Nov 26
4:55 pm - 10:59 pmMDW-SJC
8h 04m1 stop
6:58 pm - 8:51 amSJC-MDW
11h 53m2 stops
$1,101Delta
Find Deal
Sat, Nov 23 - Tue, Nov 26
6:25 pm - 9:10 pmMDW-SJC
4h 45mnonstop
7:55 am - 2:05 pmSJC-MDW
4h 10mnonstop
$1,120Southwest
Find Deal
Sat, Nov 23 - Sun, Nov 24
5:15 pm - 10:50 pmMDW-SJC
7h 35m1 stop
7:55 am - 2:05 pmSJC-MDW
4h 10mnonstop
$1,125Southwest
Find Deal
Sat, Nov 23 - Sun, Nov 24
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
$374Southwest
Find Deal
Wed, Jan 8 - Wed, Jan 15
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
8:00 am - 2:05 pmSJC-MDW
4h 05mnonstop
$404Southwest
Find Deal
Sun, Jan 12 - Sat, Jan 18
3:25 pm - 6:10 pmMDW-SJC
4h 45mnonstop
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
$419Southwest
Find Deal
Sat, Jan 11 - Sun, Jan 19
8:35 am - 11:25 amMDW-SJC
4h 50mnonstop
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
$434Southwest
Find Deal
Fri, Jan 24 - Sun, Jan 26
3:25 pm - 6:10 pmMDW-SJC
4h 45mnonstop
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
$454Southwest
Find Deal
Sat, Jan 11 - Mon, Jan 20
9:50 am - 12:35 pmMDW-SJC
4h 45mnonstop
7:55 am - 2:05 pmSJC-MDW
4h 10mnonstop
$482Southwest
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:45 am - 12:35 pmMDW-SJC
4h 50mnonstop
11:50 am - 5:55 pmSJC-MDW
4h 05mnonstop
$484Southwest
Find Deal
Fri, Jan 17 - Mon, Jan 20
7:20 pm - 10:00 pmMDW-SJC
4h 40mnonstop
6:50 am - 12:55 pmSJC-MDW
4h 05mnonstop
$489Southwest
Find Deal
Sat, Mar 22 - Sat, Mar 29
6:25 pm - 9:00 pmMDW-SJC
4h 35mnonstop
1:35 pm - 7:45 pmSJC-MDW
4h 10mnonstop
$504Southwest
Find Deal
Fri, Apr 25 - Sun, Apr 27
9:50 am - 12:35 pmMDW-SJC
4h 45mnonstop
11:10 am - 5:15 pmSJC-MDW
4h 05mnonstop
$562Southwest
Find Deal
Wed, Jan 1 - Wed, Jan 8

Frontier flights from Chicago Midway Airport to San Jose

Our best Frontier deals on Chicago Midway Airport to San Jose flight tickets
Frontier
Feb 10
MDW7:15 amChicago Midway
6h 56m
1 stop
SJC12:11 pmSan Jose
Feb 12
SJC4:03 pmSan Jose
6h 14m
1 stop
MDW12:17 amChicago Midway
Frontier
Jan 20
MDW7:15 amChicago Midway
6h 56m
1 stop
SJC12:11 pmSan Jose
Jan 23
SJC1:11 pmSan Jose
9h 06m
1 stop
MDW12:17 amChicago Midway
Frontier
Dec 16
MDW7:15 amChicago Midway
6h 53m
1 stop
SJC12:08 pmSan Jose
Jan 25
SJC5:19 pmSan Jose
16h 25m
1 stop
MDW11:44 amChicago Midway

Delta flights from Chicago Midway Airport to San Jose

Our best Delta deals on Chicago Midway Airport to San Jose flight tickets
Delta
Dec 18
MDW2:15 pmChicago Midway
8h 52m
1 stop
SJC9:07 pmSan Jose
Dec 25
SJC6:15 amSan Jose
8h 56m
1 stop
MDW5:11 pmChicago Midway
Delta
Feb 8
MDW11:19 amChicago Midway
11h 32m
2 stops
SJC8:51 pmSan Jose
Feb 15
SJC6:20 amSan Jose
9h 27m
1 stop
MDW5:47 pmChicago Midway
Delta
Jan 12
MDW1:26 pmChicago Midway
9h 44m
1 stop
SJC9:10 pmSan Jose
Jan 18
SJC5:45 amSan Jose
10h 02m
2 stops
MDW5:47 pmChicago Midway

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?

In general, October 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 $289. If you aren’t able to travel to San Jose during the month of October, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $304.

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 Tuesday when prices can be found for as low as $373. 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 Monday as prices are generally higher than usual. According to our data, the average ticket price to San Jose on Monday is $523.

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 at noon. Flights from Chicago Midway Airport to San Jose during this time can be as low as $292. In contrast, the most expensive time of day to depart to San Jose is in the evening when prices are around $461.

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

How far in advance should I book a flight to San Jose?

We recommend purchasing flights from Chicago Midway Airport to San Jose 22 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to San Jose for $405. However, in the past 72 hours, people saw flights from Chicago Midway Airport for as low as $161.

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

There are 1 cabin classes 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 67% 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

$61

Fastest flight time

4h 35m

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 $61. The best round-trip flight deal from Chicago Midway Airport to San Jose found on momondo in the last 72 hours is $126.
The fastest flight from Chicago Midway Airport to San Jose takes 4h 35m
Direct flights go from Chicago Midway Airport to San Jose every day.
There is 1 airport near San Jose: San Jose (SJC)

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $236Free CancellationRating
8.0
8,755 reviews
Search Delta flights
SouthwestPriceFrom $423Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
  • Southwest Flights From Chicago Midway Airport to San Jose

    Across 8 Southwest flights from Chicago Midway Airport to San Jose this week, the average price was $519, with the best Southwest deals starting from $423 round-trip. 5,005 users have rated Southwest on momondo, with an average score of 8.1/10.


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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