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Cheap flights from San José to Chicago from $206

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from San José to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:00 am - 4:14 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 15m1 stop Atlanta Hartsfield-Jackson
$366Delta
Fri, Dec 4 - Wed, Dec 9
Delta Logo
2:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 1:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Atlanta Hartsfield-Jackson
$366Delta
Fri, Nov 6 - Sat, Nov 14
Delta Logo
7:00 am - 4:14 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Fri, Dec 4 - Wed, Dec 9
Delta Logo
7:00 am - 6:04 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
11h 04m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Fri, Dec 4 - Wed, Dec 9
Delta Logo
7:00 am - 10:56 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Thu, Dec 3 - Tue, Dec 8
Delta Logo
2:30 pm - 10:56 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 26m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Wed, Dec 2 - Mon, Dec 7
Delta Logo
7:00 am - 10:56 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:28 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 47m1 stop Atlanta Hartsfield-Jackson
$366Delta
Thu, Dec 3 - Tue, Dec 8
JetBlue Logo
1:15 pm - 10:05 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
7h 50m1 stop Houston Hobby
JetBlue Logo
5:25 am - 6:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
14h 20m1 stop Houston Hobby
$370JetBlue
Sat, Sep 19 - Mon, Sep 28
Southwest Logo
1:00 pm - 10:15 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 15m1 stop Houston Hobby
Southwest Logo
5:45 am - 12:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 20m1 stop Orlando
$375Southwest
Sat, Oct 10 - Tue, Oct 20
Southwest Logo
1:00 pm - 10:15 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 15m1 stop Houston Hobby
Southwest Logo
12:25 pm - 7:40 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 15m1 stop Houston Hobby
$375Southwest
Sat, Oct 3 - Wed, Oct 21

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Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Nov 6
SJO2:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
Nov 14
MDW6:00 amChicago Midway
7h 05m
1 stop
SJO1:05 pmSan José Juan Santamaria Intl
$366
Delta
Oct 21
SJO1:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
Oct 25
MDW6:04 amChicago Midway
6h 56m
1 stop
SJO12:00 pmSan José Juan Santamaria Intl
$384
Delta
Oct 22
SJO1:25 pmSan José Juan Santamaria Intl
22h 22m
2 stops
MDW12:47 pmChicago Midway
Oct 30
MDW6:04 amChicago Midway
6h 56m
1 stop
SJO12:00 pmSan José Juan Santamaria Intl
$402

JetBlue flights from San José to Chicago Midway Airport

Our best JetBlue deals on San José to Chicago Midway Airport flight tickets
JetBlue
Sep 19
SJO1:15 pmSan José Juan Santamaria Intl
7h 50m
1 stop
MDW10:05 pmChicago Midway
Sep 28
MDW5:25 amChicago Midway
14h 20m
1 stop
SJO6:45 pmSan José Juan Santamaria Intl
$370
JetBlue
Sep 19
SJO1:15 pmSan José Juan Santamaria Intl
7h 50m
1 stop
MDW10:05 pmChicago Midway
Sep 26
MDW6:05 pmChicago Midway
18h 30m
1 stop
SJO11:35 amSan José Juan Santamaria Intl
$378
JetBlue
Sep 19
SJO1:15 pmSan José Juan Santamaria Intl
7h 50m
1 stop
MDW10:05 pmChicago Midway
Sep 29
MDW10:50 amChicago Midway
8h 55m
1 stop
SJO6:45 pmSan José Juan Santamaria Intl
$386

momondo Fare Finder

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

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Depart

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Price

Cheapest round-trip

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Fri 12/4

7:00 am-4:14 pm

1 stop9h 14m

Chicago Midway

Wed 12/9

1:00 pm-10:15 pm

1 stop9h 15m

$366
Quickest round-trip

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Fri 11/6

2:25 pm-10:33 pm

1 stop8h 08m

Chicago Midway

Sat 11/14

6:00 am-1:05 pm

1 stop7h 05m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Fri 12/4

7:00 am-4:14 pm

1 stop9h 14m

Chicago Midway

Wed 12/9

9:30 am-10:15 pm

2 stops12h 45m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Fri 12/4

7:00 am-6:04 pm

2 stops11h 04m

Chicago Midway

Wed 12/9

9:30 am-10:15 pm

2 stops12h 45m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 12/3

7:00 am-10:56 pm

1 stop15h 56m

Chicago Midway

Tue 12/8

9:30 am-10:15 pm

2 stops12h 45m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Wed 12/2

2:30 pm-10:56 pm

1 stop8h 26m

Chicago Midway

Mon 12/7

9:30 am-10:15 pm

2 stops12h 45m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 12/3

7:00 am-10:56 pm

1 stop15h 56m

Chicago Midway

Tue 12/8

11:28 am-10:15 pm

1 stop10h 47m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 9/19

1:15 pm-10:05 pm

1 stop7h 50m

Chicago Midway

Mon 9/28

5:25 am-6:45 pm

1 stop14h 20m

$370

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 10/10

1:00 pm-10:15 pm

1 stop8h 15m

Chicago Midway

Tue 10/20

5:45 am-12:05 pm

1 stop7h 20m

$375

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 10/3

1:00 pm-10:15 pm

1 stop8h 15m

Chicago Midway

Wed 10/21

12:25 pm-7:40 pm

1 stop8h 15m

$375

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from San José 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 José and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $427 to $644.
The lowest price recently found on this route was $366.

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 José, with most prices found around $358. If you are unable to visit Chicago Midway Airport during the month of November, then departing from San José during the month January is also very affordable. Most momondo users find prices during this month for around $385.

When to book flights from San José to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San José 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 José to Chicago Midway Airport (SJO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José to Chicago Midway Airport

Best Price Found

$206

Fastest flight time

7h 35m

Direct flights

None
The best one-way flight to Chicago Midway Airport from San José in the past 72 hours is $206. The best round-trip flight deal from San José to Chicago Midway Airport found on momondo in the last 72 hours is $366.
The fastest flight from San José to Chicago Midway Airport takes 7h 35m
There are no direct flights from San José to Chicago Midway Airport. There are no popular flight routes from San José to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from San José to Chicago Midway Airport

  • How far is San José Juan Santamaria Intl to Chicago Midway by plane?

    San José Juan Santamaria Intl and Chicago Midway are 2210.5 mi apart from one another. Typically, this will take 7h 35m by plane in normal conditions.

  • When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Chicago Midway Airport?

    Prices for flights from San José Juan Santamaria Intl Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from San José Juan Santamaria Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway 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 Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from San José to Chicago Midway Airport

Compare and see reviews for airlines that fly from San José to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $390Free CancellationRating
8.0
4,215 reviews
Search Southwest flights

Traveling to a place near Chicago?

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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San José to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from San José to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San José to Chicago.

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

Price alerts on flights to Chicago from San José 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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