$84 Cheap flight deals from San Jose (SJC) to Chicago (CHI)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
This Weekend's Flight Deals from San Jose to Chicago
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $84 One Way, $165 Round Trip from San Jose to Chicago
Prices starting at $165 for return flights and $84 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Chicago economy flight packages
Eurostars Magnificent Mile
Jun 3 - Jun 7
San Jose (SJC) to Chicago (ORD)
Reviewed on Oct 18, 2025
Hotel Riu Plaza Chicago
Jun 3 - Jun 7
San Jose (SJC) to Chicago (ORD)
Reviewed on Jan 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Jun 3 - Jun 7
San Jose (SJC) to Chicago (ORD)
Reviewed on Nov 3, 2025
More About Flying To Chicago from San Jose
Route Information for Flights from San Jose to Chicago
Origin Airport IATA Code | SJC |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
San Jose to Chicago
Planning a romantic getaway, traveling the world at last or flying out to see the kids and grandkids? Orbitz On-the-Go saves you both time and money. Our cutting edge mobile tools and guaranteed low prices leave plenty of room in your budget for the important things in life. Find same-day deals on domestic flights from San Jose to Chicago, and bargain sales on international San Jose to Chicago flights.
Family Matters, and So Do Cheap Tickets
Don’t miss another birthday, graduation or wedding, wherever they are. Take advantage of Orbitz On-the-Go’s discount travel planning features to save on flights from San Jose to Chicago and San Jose to Chicago flights. Tell them you’ll be there, every single time.
Escape to Romance
Treat yourself and the one you love to a romantic hideaway. Orbitz budget air flights from San Jose to Chicago and San Jose to Chicago flights can be bundled into packages for extravagant savings at spa resorts and hotels.
See the World
It’s finally your time. Go wherever the wind takes you. Orbitz On-the-Go makes dreams come true. Book low fare flights from San Jose to Chicago, the world is at your fingertips.
Flight or Gate Changes? No Problem
Once you’ve reserved your low cost air ticket on San Jose to Chicago flights or flights from San Jose to Chicago, stay informed with Orbitz On-the-Go free alerts. Choose from email, voice and text notification. You’ll always know your flight status and gate number, and where and how to pick up your bags.
Frequently asked questions
- Flights to Chicago
- Flights from San Jose
- San Jose Airports
- Chicago Airports
- Airlines Operating
- Flights To
Flights to Chicago
- New York to Chicago
- Houston to Chicago
- Phoenix to Chicago
- Dallas to Chicago
- Toronto to Chicago
- Orlando to Chicago
- Las Vegas to Chicago
- Los Angeles to Chicago
- Washington to Chicago
- San Francisco to Chicago
- Detroit to Chicago
- Montreal to Chicago
- New Orleans to Chicago
- Sacramento to Chicago
- Hartford to Chicago
- Kansas City to Chicago
- Paris to Chicago
- London to Chicago
- Rome to Chicago
- Harrisburg - Hershey to Chicago
Flights from San Jose
- San Jose to Los Angeles
- San Jose to Dallas
- San Jose to Phoenix
- San Jose to Chicago
- San Jose to Toronto
- San Jose to New Orleans
- San Jose to Paris
- San Jose to Eureka
- San Jose to Charlotte
- San Jose to London
- San Jose to New York
- San Jose to San Francisco
- San Jose to Edmonton
- San Jose to Detroit
- San Jose to Houston
- San Jose to Seattle
- San Jose to Washington
San Jose Airports
More Destinations
- Flights from Atlanta to Southwest Side
- Flights from Dallas to Southwest Side
- Flights from Phoenix to Southwest Side
- Flights from San Francisco to Southwest Side
- Flights from Guadalajara to Oak Park
- Flights from Atlanta to Oak Park
- Flights from Boston to Oak Park
- Flights from Dallas to Oak Park
- Flights from Helsinki to Oak Park
- Flights from Miami to Oak Park
- Flights from Philadelphia to Oak Park
- Flights from Phoenix to Oak Park
- Flights from San Francisco to Oak Park
- Flights from Seattle to Oak Park
- Flights from Fort Lauderdale to Oak Park
- Flights from Oakland to Oak Park
- Flights from Savannah to Oak Park
- Flights from Shenzhen to Oak Park
- Flights from Las Vegas to Schiller Park
- Flights from Mexico City to Schiller Park
- Flights from Fort Lauderdale to Schiller Park
- Flights from Atlanta to Cicero
- Flights from Austin to Cicero
- Flights from Baltimore to Cicero
- Flights from Beijing to Cicero
- Flights from Boston to Cicero
- Flights from Charlotte to Cicero
- Flights from Dallas to Cicero
- Flights from Denver to Cicero
- Flights from Houston to Cicero
- Flights from Las Vegas to Cicero
- Flights from Los Angeles to Cicero
- Flights from New York to Cicero
- Flights from Philadelphia to Cicero
- Flights from Phoenix to Cicero
- Flights from San Francisco to Cicero
- Flights from Boston to Glenview
- Flights from Houston to Glenview
- Flights from Miami to Glenview
- Flights from Tampa to Glenview
- Flights from Buffalo (BUF) to Chicago (MDW)
- Flights from Charlotte (CLT) to Chicago (MDW)
- Flights from Cincinnati (CVG) to Chicago (MDW)
- Flights from Houston (HOU) to Chicago (MDW)
- Flights from Indianapolis (IND) to Chicago (MDW)
- Flights from Jackson (JAN) to Chicago (MDW)
- Flights from Marion (MWA) to Chicago (MDW)
- Flights from Oklahoma City (OKC) to Chicago (MDW)
- Flights from Sarasota (SRQ) to Chicago (MDW)
- Flights from Tampa (TPA) to Chicago (MDW)
- Flights from Beijing to Evanston
- Flights from Miami to Evanston
- Flights from Orlando to Evanston
- Flights from Portland to Evanston
- Flights from Raleigh to Evanston
- Flights from Fort Lauderdale to Evanston
- Flights from Savannah to Evanston
- Flights from Austin (AUS) to Chicago (ORD)
- Flights from Nashville (BNA) to Chicago (ORD)
- Flights from Boise (BOI) to Chicago (ORD)
- Flights from Boston (BOS) to Chicago (ORD)
- Flights from Charleston (CHS) to Chicago (ORD)
- Flights from Cedar Rapids (CID) to Chicago (ORD)
- Flights from Charlotte (CLT) to Chicago (ORD)
- Flights from Columbus (CMH) to Chicago (ORD)
- Flights from Columbia (COU) to Chicago (ORD)
- Flights from Cincinnati (CVG) to Chicago (ORD)
- Flights from Dallas (DAL) to Chicago (ORD)
- Flights from Delhi (DEL) to Chicago (ORD)
- Flights from Denver (DEN) to Chicago (ORD)
- Flights from Des Moines (DSM) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Dubai (DXB) to Chicago (ORD)
- Flights from Grand Rapids (GRR) to Chicago (ORD)
- Flights from White Plains (HPN) to Chicago (ORD)
- Flights from Seoul (ICN) to Chicago (ORD)
- Flights from Jacksonville (JAX) to Chicago (ORD)
- Flights from Chennai (MAA) to Chicago (ORD)
- Flights from Kansas City (MCI) to Chicago (ORD)
- Flights from Harrisburg (MDT) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from Milwaukee (MKE) to Chicago (ORD)
- Flights from Madison (MSN) to Chicago (ORD)
- Flights from Ontario (ONT) to Chicago (ORD)
- Flights from West Palm Beach (PBI) to Chicago (ORD)
- Flights from Portland (PDX) to Chicago (ORD)
- Flights from Beijing (PEK) to Chicago (ORD)
- Flights from Peoria (PIA) to Chicago (ORD)
- Flights from Shanghai (PVG) to Chicago (ORD)
- Flights from San Diego (SAN) to Chicago (ORD)
- Flights from San Antonio (SAT) to Chicago (ORD)
- Flights from Savannah (SAV) to Chicago (ORD)
- Flights from Louisville (SDF) to Chicago (ORD)
- Flights from San Jose (SJC) to Chicago (ORD)
- Flights from Salt Lake City (SLC) to Chicago (ORD)
- Flights from Sacramento (SMF) to Chicago (ORD)
- Flights from St. Louis (STL) to Chicago (ORD)
- Flights from Trenton (TTN) to Chicago (ORD)
- Flights from Knoxville (TYS) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.