flıghtmap
SkyView
Hotels
FlightsGuidesMoreMembership
Log In

Direct flights from San Jose to Chicago

Did you mean Flights from Chicago to San Jose?

Flightmap/Flights from SJC/SJC to MDW

San Jose

United States

SJC

Norman Y. Mineta San Jose International Airport

Chicago

United States

MDW

Chicago Midway International Airport

Route
Nonstop service available
Distance
1,833 miles
Marketing airlines
1 airline
Aircraft
4 aircraft types
Dates
Oct 19, 2026 – Aug 2, 2027

Observed award fares

A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.

Departure window: 2026-10-23 – 2026-11-21.

No recent fares appear in this limited preview. This does not mean the route is sold out. Use the search controls to check other dates and routes.

Explore flight routesCompare transfer partnersLearn how to book with points

Explore these airports and cities

  • Flights from SJC
  • Flights to MDW
  • Award flights to Chicago

San Jose to Chicago route overview

Norman Y. Mineta San Jose International Airport (SJC) serves San Jose; Chicago Midway International Airport (MDW) serves Chicago.

The airports are 1,833 miles apart by great-circle distance.

Roame's current schedule feed shows nonstop service from SJC to MDW.

Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.

Published schedule dates span Oct 19, 2026 – Aug 2, 2027.

Marketing airlines on the San Jose to Chicago route

These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.

Aircraft flying from SJC to MDW

Frequently asked questions

Which airports serve the San Jose to Chicago route?

Norman Y. Mineta San Jose International Airport (SJC) is the origin airport and Chicago Midway International Airport (MDW) is the destination airport.

How far is Chicago from San Jose?

SJC and MDW are approximately 1,833 miles apart by great-circle distance.

Are there direct flights from SJC to MDW?

Yes. Roame's current schedule feed shows nonstop service from SJC to MDW.

Which airlines market flights from SJC to MDW?

Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.

Which aircraft fly from SJC to MDW?

Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H), Boeing 737 MAX 8 (7M8), 7S7 and JET.

More routes from San Jose

  • LAXLos AngelesUnited States
  • SANSan DiegoUnited States
  • SEASeattleUnited States
  • PHXPhoenixUnited States
  • LASLas VegasUnited States
  • PDXPortlandUnited States
  • SLCSalt Lake CityUnited States
  • DENDenverUnited States
  • SNASanta AnaUnited States
  • BURBurbankUnited States
  • DFWDallas-Fort WorthUnited States
  • AUSAustinUnited States
Get the app
Download on the App Store
Flights
SearchDiscoverSkyViewFlightMapsNEW
Hotels
SearchDeals on Stays
About
MembershipAbout usGift CardsGiveawaysHow it works
Resources
Credit CardsGuidesNewsletterRSS FeedAdvertise with usBecome an affiliate
Support
FAQDirectoryHelp centerContact usTerms of servicePrivacy policy
Get the app
Download on the App Store
Follow us
®

The fastest search engine for points travel.

© Copyright 2026 Roame Holdings, Inc. All Rights Reserved.
Sign Up
SearchGuides