Book with Aviafares
Aviafares brings you some of the best San Jose to Chicago fares we're seeing right now. These are our latest lead-in prices, pulled from the same booking system our US agents work. Don't keep waiting. Book them before they move.
Wed, Jun 17 - Sun, Jun 28
From
$695.99
Sun, May 31 - Thu, Jun 11
From
$758.99
Mon, Jun 29 - Sat, Jul 11
From
$347.99
Indicative fares based on historical lead-in pricing for San Jose–Chicago; live search above returns today's bookable offers.
Need help booking San Jose to Chicago? Talk to a US agent.
Unpublished consolidator rates on premium cabins, 24/7.
4 scheduled routes connect San Jose, Philippines with Chicago, United States in our booking network. Top carriers on this route by route count are American Airlines, Southwest Airlines, United Airlines.
You can book San Jose to Chicago flights through Aviafares at the same published fares you'd see on the airline's own site, and our US booking team also pulls unpublished consolidator rates on premium cabins. If you need help with a complex itinerary, a schedule change, or just want a second opinion on the best routing, call our 24/7 line.
San Jose is served by 5 airports: Evelio Javier Airport (EUQ), Juan Santamaria International Airport (SJO), Norman Y. Mineta San Jose International Airport (SJC), Reid-Hillview Airport of Santa Clara County (RHV), San Jose Airport (SJI). Chicago is served by 4 airports: Chicago Meigs Airport (CGX), Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), Waukegan National Airport (UGN). Search pulls fares across every combination by default, but you can pin a specific pair if you have a preference.
Changes, cancellations, schedule irregularities, and refunds on your San Jose–Chicago ticket are handled by our US-based booking team around the clock. If your flight is cancelled or rescheduled, we rebook you on the next available option at the airline's published fees. Call the number at the top of this page or request a callback.
Active carriers with scheduled service on this city pair, ranked by route count.
Routes connected to San Jose or Chicago that our US agents book every day.
Our 24/7 US booking team knows fare rules, change policies, and unpublished consolidator rates on San Jose–Chicago cold. One call gets you a real answer.