Cheap flights from San José to Chicago Midway

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

How much is a flight from San José to Chicago Midway?

Depending on when you travel and how far in advance you book, fares between San José and Chicago can differ a lot.

Select your dates to check current offers.

Low-cost airlines offer competitive fares, but often add charges for extra services. Keep that in mind when planning your trip. Also, midweek departures may offer better deals than weekends.

Is there more than one airport in San José or Chicago?

Even short-haul routes can benefit from considering secondary airports. It may open up more flight times or cheaper fares.

  • Airports in San José: One more airport is available besides San José - Juan Santamaria International, Tobias Bolanos.
  • Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.

Airports with more daily flights offer more flexibility if plans change or delays occur. If you’re flexible, consider airports near Chicago as well.

Flights from San José - Juan Santamaria International to Chicago - Midway

Adjust your flight filters for San José – Chicago Midway

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from the best travel agencies and carriers.

Other popular destinations

Planning a trip to United States? These cities are popular too: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.
Frequently Asked Questions

Frequently asked questions about flights from San José to Chicago Midway.

How much does an airline ticket from San José to Chicago Midway cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from San José to Chicago Midway.

How far is San José from Chicago?

San José is about 3551 km from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in San José?

San José has another airport: Tobias Bolanos.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from San José to Chicago?

This information is not available at the moment.

What is the cheapest month to fly from San José to Chicago?

This information is not available at the moment.

What is the most expensive month to fly from San José to Chicago?

This information is not available at the moment.

What is the best day of the week to fly from San José to Chicago?

This information is not available at the moment.