Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San José to Chicago from $235

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
2:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 10m1 stop Atlanta Hartsfield-Jackson
$366Delta
Sat, Nov 7 - Wed, Nov 11
Delta Logo
1:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 56m1 stop Atlanta Hartsfield-Jackson
$387Delta
Sat, Oct 24 - Thu, Oct 29
Southwest Logo
1:50 pm - 10:50 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 00m1 stop Orlando
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
$411Southwest
Tue, Feb 9 - Tue, Feb 23
Delta Logo
1:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 56m1 stop Atlanta Hartsfield-Jackson
$416Delta
Sat, Oct 24 - Thu, Oct 29
Delta Logo
3:55 pm - 9:52 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
17h 57m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:35 am - 10:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
11h 30m1 stop Atlanta Hartsfield-Jackson
$416Delta
Sat, Jan 23 - Sat, Jan 30
Delta Logo
3:55 pm - 9:52 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
17h 57m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 am - 10:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 35m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$416Delta
Sat, Jan 23 - Sat, Jan 30
Southwest Logo
1:50 pm - 10:50 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 00m1 stop Orlando
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
$432Southwest
Wed, Feb 10 - Wed, Feb 17
Southwest Logo
1:30 pm - 10:20 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
7h 50m1 stop Houston Hobby
Southwest Logo
11:50 am - 7:40 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 50m1 stop Houston Hobby
$432Southwest
Thu, Oct 22 - Thu, Oct 29
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 1:12 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 12m1 stop Atlanta Hartsfield-Jackson
$437Delta
Thu, Nov 12 - Tue, Nov 17
Southwest Logo
1:20 pm - 10:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 35m1 stop Orlando
Southwest Logo
5:15 am - 12:20 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Houston Hobby
$453Southwest
Mon, Nov 9 - Sun, Nov 15

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

JetBlue flights from San José to Chicago Midway Airport

Our best JetBlue deals on San José to Chicago Midway Airport flight tickets
JetBlue
Oct 8
SJO1:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
Oct 13
MDW6:04 amChicago Midway
6h 56m
1 stop
SJO12:00 pmSan José Juan Santamaria Intl
$475
JetBlue
Oct 14
SJO1:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
Oct 18
MDW6:04 amChicago Midway
6h 56m
1 stop
SJO12:00 pmSan José Juan Santamaria Intl
$496
JetBlue
Sep 9
SJO1:19 pmSan José Juan Santamaria Intl
8h 25m
1 stop
MDW10:44 pmChicago Midway
Sep 20
MDW6:05 amChicago Midway
6h 49m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
$511

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Nov 7
SJO2:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
Nov 11
MDW1:05 pmChicago Midway
9h 10m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
$366
Delta
Oct 24
SJO1:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
Oct 29
MDW6:04 amChicago Midway
6h 56m
1 stop
SJO12:00 pmSan José Juan Santamaria Intl
$387
Delta
Oct 24
SJO1:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
Oct 29
MDW6:04 amChicago Midway
6h 56m
1 stop
SJO12:00 pmSan José Juan Santamaria Intl
$416

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 11/7

2:25 pm-10:33 pm

1 stop8h 08m

Chicago Midway

Wed 11/11

1:05 pm-10:15 pm

1 stop9h 10m

$366
Quickest round-trip

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 10/24

1:25 pm-10:33 pm

1 stop8h 08m

Chicago Midway

Thu 10/29

6:04 am-12:00 pm

1 stop6h 56m

$387

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Tue 2/9

1:50 pm-10:50 pm

1 stop9h 00m

Chicago Midway

Tue 2/23

5:25 am-1:45 pm

1 stop8h 20m

$411

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 10/24

1:25 pm-10:33 pm

1 stop8h 08m

Chicago Midway

Thu 10/29

6:04 am-12:00 pm

1 stop6h 56m

$416

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 1/23

3:55 pm-9:52 am

1 stop17h 57m

Chicago Midway

Sat 1/30

10:35 am-10:05 pm

1 stop11h 30m

$416

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 1/23

3:55 pm-9:52 am

1 stop17h 57m

Chicago Midway

Sat 1/30

9:30 am-10:05 pm

2 stops12h 35m

$416

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Wed 2/10

1:50 pm-10:50 pm

1 stop9h 00m

Chicago Midway

Wed 2/17

5:25 am-1:45 pm

1 stop8h 20m

$432

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 10/22

1:30 pm-10:20 pm

1 stop7h 50m

Chicago Midway

Thu 10/29

11:50 am-7:40 pm

1 stop8h 50m

$432

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 11/12

2:37 pm-10:54 pm

1 stop8h 17m

Chicago Midway

Tue 11/17

6:00 am-1:12 pm

1 stop7h 12m

$437

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Mon 11/9

1:20 pm-10:55 pm

1 stop9h 35m

Chicago Midway

Sun 11/15

5:15 am-12:20 pm

1 stop7h 05m

$453

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

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 typical for flights on this route.

Typical prices usually range from $366 to $594.
The lowest price recently found on this route was $366.

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

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from San José, with most prices found around $385. If you are unable to visit Chicago Midway Airport during the month of January, then departing from San José during the month March is also very affordable. Most momondo users find prices during this month for around $401.

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

$235

Fastest flight time

7h 45m

Direct flights

None
The best one-way flight to Chicago Midway Airport from San José in the past 72 hours is $235. 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 45m
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 45m 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
4,195 reviews
Search Southwest flights

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
Porter
Crown Point
Griffith
Saint John

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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/9
Fri 10/16
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago