San Jose → Chicago flights

San Jose (SJO)→Chicago (CGX, DPA, MDW, ORD, PWK, RFD)
from€329

Last observed price · Last checked: 25 Aug 2026 · Price may change

Find flights

Short answer

The lowest fare our own searches returned is €329, seen on 25 Aug 2026. October 2026 is the cheapest month in our observations, at €329. These are prices our searches returned on the dates shown, not quotes; run a live search for today's fare.

Selected search
Last checked: 25 Aug 2026 · Price may change
€329
Wed 14 Oct 2026 → Tue 27 Oct 2026
United Airlines1 stop13 nights
Cheapest
Last checked: 25 Aug 2026 · Price may change
€329 lowest7h 52m fastest
Options found on this date
UAUnited Airlines12:44 · 1 stop€329
View ticket →

Tickets found in the last 7 days

The lowest fares our queries caught, cheapest first.

UA€329Cheapest14 Oct 2026 → 27 Oct 2026United Airlines · 1 stop · 12:44Last checked: 25 Aug 2026 · Price may change13 nightsView ticket →UA€3376 Oct 2026 → 20 Oct 2026United Airlines · 1 stop · 13:25Last checked: 25 Aug 2026 · Price may change14 nightsView ticket →

Starting prices by month

The lowest fare our queries observed in each month. Open a month to see its days; click a day with no price and we will search it for you.

Observed priceLowest monthno price observedLast checked: 25 Aug 2026
San Jose → ChicagoWed 14 Oct 2026 · €329
Find flights

Route facts

Cheapest month
October 2026
€329
Typical duration
7h 52m
Alternative airports
5
DPA, MDW, ORD, PWK, RFD

Frequently asked

Are there direct flights from San Jose to Chicago?+

Our data holds no non-stop flight from San Jose to Chicago. The fares on this page include at least one stop.

How much is a flight from San Jose to Chicago?+

The lowest fare we have observed is €329, found on 25 Aug 2026. Prices move, so read it as a floor rather than a quote.

When is the cheapest month to fly from San Jose to Chicago?+

In our observations October 2026 is the cheapest month so far, at €329.

Similar routes

San Jose → Madrid€579Mexico City → Chicago€241San Jose → New York€357Guadalajara → Chicago€286San Jose → Cancun€250Los Angeles → Chicago€124San Jose → Fort Lauderdale€308Dallas → Chicago€129

More routes from San Jose

San Jose → Madrid€579San Jose → New York€357San Jose → Cancun€250San Jose → Fort Lauderdale€308San Jose → Miami€294San Jose → Medellin€175San Jose → Orlando€340San Jose → Mexico City€252San Jose → Bogota€296San Jose → Panama City€234San Jose → Buenos Aires€514San Jose → Guatemala City€283San Jose → Washington€379San Jose → San Salvador€283San Jose → Santo Domingo€382San Jose → AntalyaSan Jose → Istanbul€1,036San Jose → Cartagena€259San Jose → Lima€367San Jose → AmsterdamSan Jose → Houston€355San Jose → FrankfurtSan Jose → Paris€867San Jose → Atlanta€486San Jose → Dallas€390San Jose → London€902San Jose → Puerto Vallarta€292San Jose → Moscow€1,438

More routes to Chicago

Mexico City → Chicago€241Guadalajara → Chicago€286Los Angeles → Chicago€124Dallas → Chicago€129New York → Chicago€155Atlanta → Chicago€92Denver → Chicago€95Minneapolis → Chicago€139Cincinnati → Chicago€125Montreal → Chicago€244Istanbul → Chicago€498Amman → Chicago€500New Orleans → Chicago€191Fort Lauderdale → Chicago€127Phoenix → Chicago€140Houston → Chicago€200Baltimore → Chicago€69Miami → Chicago€140Las Vegas → Chicago€140San Diego → Chicago€203Detroit → Chicago€194San Juan → Chicago€126Paris → Chicago€480Brussels → Chicago€686Guatemala City → Chicago€255London → Chicago€491Toronto → Chicago€161Dubai → Chicago€666Munich → Chicago€571Copenhagen → Chicago€411

Last checked: 25 Aug 2026