San Jose to Chicago Flight Tickets
Compare the best flight deals from San Jose to Chicago
About San Jose - Chicago Flights
Find the best prices for flights between San Jose (United States) and Chicago (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
San Jose has 1 airports, while Chicago has 6 airports. Compare flights between all airports to find the best deal.
Cheapest Months for San Jose - Chicago Flights
Best month to fly
May 2026 - 3,969 ₺
May 2026
3,969 ₺
1 stops
CheapestJune 2026
5,464 ₺
1 stops
November 2026
5,572 ₺
1 stops
March 2026
7,167 ₺
1 stops
April 2026
7,465 ₺
Direct
July 2026
9,311 ₺
Direct
| Ay | Flight Type | Price |
|---|---|---|
| May 2026Cheapest | 1 stops | 3.969 ₺ |
| June 2026 | 1 stops | 5.464 ₺ |
| November 2026 | 1 stops | 5.572 ₺ |
| March 2026 | 1 stops | 7.167 ₺ |
| April 2026 | Direct | 7.465 ₺ |
| July 2026 | Direct | 9.311 ₺ |
Prices may change. Based on recent searches.
Popular San Jose - Chicago Flights
San Jose - Chicago
Chicago - San Jose
Airlines on San Jose - Chicago Route
| Havayolu | Uçuş Tipi | Fiyat |
|---|---|---|
 Frontier Airlines | 1 stops | 7.167 ₺ |
 Hawaiian Airlines | 1 stops | 8.148 ₺ |
San Jose Airports
Chicago Airports
Alternative Routes
Alternative Routes from San Jose
San Jose - Chicago Flight Summary
Cheaper tickets are usually available on weekdays and with early bookings.
San Jose and Chicago - Airport Transportation
O'Hare International Airport (ORD)
From Airport to City Center
Metro/Train: The CTA Blue Line Train is the most convenient option for transportation from O'Hare International Airport to downtown Chicago. The airport station is directly connected to Terminals 1, 2, and 3. Access from Terminal 5 is possible via a free shuttle train. The journey takes approximately 40-45 minutes. Services operate 24 hours a day, with trains running every 5-10 minutes during peak hours.
Bus (CTA and Private Shuttles): Buses connecting O'Hare Terminals 1, 2, 3, and 5 operate routes to downtown. The journey time varies between 45-60 minutes depending on traffic conditions. Services run every 15-30 minutes and generally operate from 5:00 AM to 11:45 PM.
Taxi: Official taxi stands at O'Hare are located at each terminal exit and provide direct transportation to downtown. The journey time varies between 30-60 minutes depending on traffic. Taxi services are available 24 hours a day.
Airport App-Based Rides (Uber/Lyft): Apps like Uber and Lyft operate in designated pickup areas at O'Hare. Journey time and cost can vary based on traffic and demand.
Car Rental: Various car rental companies are available at the airport. Car rental options can be arranged at offices located at terminal exits or at rental centers accessible via shuttle services.