Find the cheapest flights from San José to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
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.Southwest flights from San José to Chicago Midway Airport
Our best Southwest deals on San José to Chicago Midway Airport flight tickets
Delta flights from San José to Chicago Midway Airport
Our best Delta deals on San José to Chicago Midway Airport flight tickets
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
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sat 11/7
2:25 pm-9:32 am
2 stops19h 07m
Chicago Midway
Thu 11/12
6:00 am-10:15 pm
1 stop16h 15m
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
Thu 11/12
6:00 am-10:15 pm
1 stop16h 15m
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Wed 11/4
2:25 pm-9:32 am
2 stops19h 07m
Chicago Midway
Thu 11/12
1:05 pm-10:15 pm
1 stop9h 10m
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Wed 11/4
2:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Thu 11/12
11:27 am-10:15 pm
1 stop10h 48m
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Sun 11/1
2:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Thu 11/12
6:00 am-10:15 pm
1 stop16h 15m
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Tue 11/3
2:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Thu 11/12
11:27 am-10:15 pm
1 stop10h 48m
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Wed 11/4
2:15 pm-11:10 pm
1 stop8h 55m
Chicago Midway
Sun 11/8
5:15 am-12:20 pm
1 stop7h 05m
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Wed 11/4
2:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Wed 11/11
6:00 am-10:15 pm
1 stop16h 15m
San JoséChicago
SJO San José Juan Santamaria Intl - MDW Chicago Midway
SJOMDW
San José Juan Santamaria Intl
Wed 11/4
2:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Fri 11/13
6:00 am-10:15 pm
1 stop16h 15m
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
Mon 10/26
7:50 am-7:40 pm
2 stops12h 50m
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 low for flights on this route.
Typical prices usually range from $436 to $556.The lowest price recently found on this route was $388.
Which airport is the most popular layover for flights between San José and Chicago Midway Airport?
Houston (HOU) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.
Which layover airport offers the lowest fares from San José to Chicago Midway Airport?
Flights via Houston (HOU) offer the lowest average round-trip price of $816.
Which layover airport has the shortest travel time from San José to Chicago Midway Airport?
Flights connecting via Houston (HOU) have the shortest average one-way travel time: 8h 00m.
Which layover airport has the shortest connection time from San José to Chicago Midway Airport?
Atlanta (ATL) has the shortest average layover time for this route: 1h 29m.
When to book flights from San José to Chicago Midway Airport
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
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 50m 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?
There is 1 operator available for flights from San José Juan Santamaria Intl Airport to Chicago Midway Airport as of October 2026.
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?
Based on momondo bookings for this flight route, the most popular airline on flight routes from San José to Chicago Midway Airport is Southwest (100% of total bookings).
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 | ||
|---|---|---|---|---|---|
| PriceFrom $390 | Free Cancellation | Rating 8.0 4,213 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy 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.