Cheap flights from San Jose to Chicago

Flights overview

Useful information for finding cheap flights from San Jose to Chicago and booking your next trip
Cheapest round-trip flights $210
Frontier 1 stop 16 hr Thu, May 28 — Fri, Jun 5
The cheapest round-trip flight from San Jose to Chicago is currently $210
Cheapest one-way flight $111
Frontier 1 stop 16 hr Thu, May 28
The cheapest one-way flight from San Jose to Chicago is currently $111
Cheapest nonstop flights $363
Southwest Nonstop 5 hr Thu, May 28 — Thu, Jun 4
The cheapest nonstop round-trip flight from San Jose to Chicago is currently $363
Last-minute weekend getaway $444
Frontier 1 stop 8 hr Fri, Apr 24 — Mon, Apr 27
The cheapest last-minute weekend getaway from San Jose to Chicago is currently $444
Cheapest business class flights $458
Frontier 1 stop 16 hr Thu, May 28 — Fri, Jun 5
The cheapest business class round-trip flight from San Jose to Chicago is currently $458
Fastest flight 4 hr 5 min The fastest nonstop flight from San Jose to Chicago takes 4 hr 5 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from San Jose to Chicago is typically September. The most expensive month to fly is typically December.
September
Cheapest
Typical prices: $170–275
December
Most expensive
Typical prices: $280–600

Popular airlines from San Jose to Chicago

  • Southwest
    Nonstop
    from $339
    Typical price: $330–610
    13 weekly nonstop flights
    SJC - MDW Every day
    2950 weekly connecting flights
    SJC - MDW, ORD Every day
  • United
    Nonstop
    from $407
    Typical price: $360–670
    7 weekly nonstop flights
    SJC - ORD Every day
    96 weekly connecting flights
    SJC - ORD Every day
  • American
    from $427
    Typical price: $380–670
    241 weekly connecting flights
    SJC - ORD Every day
  • Delta
    from $427
    Typical price: $305–710
    207 weekly connecting flights
    SJC - MDW, ORD Every day
  • Alaska
    from $325
    Typical price: $290–660
    85 weekly connecting flights
    SJC - ORD Every day
  • Frontier
    from $210
    Typical price: $220–570
    16 weekly connecting flights
    SJC - ORD Every Mon, Thu, Fri, Sun

Popular airports near San Jose

  • San Jose Mineta International Airport (SJC)
    San Jose United States 13 min 2 mi
  • San Francisco International Airport (SFO)
    San Francisco United States 42 min 33 mi
  • Sacramento International Airport (SMF)
    Sacramento United States 2 hr 1 min 94 mi
  • Oakland San Francisco Bay Airport (OAK)
    Oakland United States 43 min 32 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from San Jose to Chicago

The cheapest flights from San Jose to Chicago are usually in September. Typical ticket prices in September range from $170 to $275.
The cheapest round-trip flight from San Jose to Chicago recently found on Google Flights was with Frontier from $210. The cheapest one-way flight was with Frontier from $111.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San Jose to Chicago is $339, flying from May 28 to Jun 3.
  • The cheapest United flight from San Jose to Chicago is $407, flying from Jul 9 to Jul 15.
  • The cheapest American flight from San Jose to Chicago is $427, flying from May 28 to Jun 3.
  • The cheapest Delta flight from San Jose to Chicago is $427, flying from May 28 to Jun 3.
  • The cheapest Alaska flight from San Jose to Chicago is $325, flying from May 28 to Jun 3.
  • The cheapest Frontier flight from San Jose to Chicago is $210, flying from May 28 to Jun 5.
The cheapest round-trip flight from San Jose to Chicago starts at $210 from Thu, May 28 to Fri, Jun 5. The cheapest one-way flight starts at $111 and departs on Thu, May 28.
4 hr 5 min is the shortest flight time from San Jose to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from San Jose to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from San Jose to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from San Jose to Chicago.

In terms of nonstop flights, Southwest is the most popular. Southwest offers 13 nonstop flights and 2,950 connecting flights per week. Southwest flies from San Jose Mineta International Airport (SJC) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from San Jose to Chicago are:
  • United offers 7 nonstop flights and 96 connecting flights per week. United flies from San Jose Mineta International Airport (SJC) to Chicago O'Hare International Airport (ORD) .
  • American offers 241 connecting flights per week. American flies from San Jose Mineta International Airport (SJC) to Chicago O'Hare International Airport (ORD) .
  • Delta offers 207 connecting flights per week. Delta flies from San Jose Mineta International Airport (SJC) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Alaska offers 85 connecting flights per week. Alaska flies from San Jose Mineta International Airport (SJC) to Chicago O'Hare International Airport (ORD) .
  • Frontier offers 16 connecting flights per week. Frontier flies from San Jose Mineta International Airport (SJC) to Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between San Jose and Chicago.
The cheapest round-trip flight from San Jose to Chicago recently found on Google Flights was with Frontier from $210. The cheapest one-way flight was with Frontier from $111.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San Jose to Chicago is $339, flying from May 28 to Jun 3.
  • The cheapest United flight from San Jose to Chicago is $407, flying from Jul 9 to Jul 15.
  • The cheapest American flight from San Jose to Chicago is $427, flying from May 28 to Jun 3.
  • The cheapest Delta flight from San Jose to Chicago is $427, flying from May 28 to Jun 3.
  • The cheapest Alaska flight from San Jose to Chicago is $325, flying from May 28 to Jun 3.
  • The cheapest Frontier flight from San Jose to Chicago is $210, flying from May 28 to Jun 5.
Southwest and United fly direct from San Jose to Chicago.
  • There are 13 Southwest direct flights from San Jose to Chicago per week. Flights are available every day.
  • There are 7 United direct flights from San Jose to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between San Jose and Chicago at price $444 is offered by Frontier from Fri, Apr 24 to Mon, Apr 27.
Southwest and United fly direct from San Jose to Chicago.
  • There are 13 Southwest direct flights from San Jose to Chicago per week. Flights are available every day.
  • There are 7 United direct flights from San Jose to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from San Jose to Chicago on a daily basis.
The cheapest direct (nonstop) round-trip flights between San Jose and Chicago start at $363 from Thu, May 28 to Thu, Jun 4 with Southwest.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from San Jose to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between San Jose and Chicago start at $458 from Thu, May 28 to Fri, Jun 5 with Frontier.
The cheapest economy class round-trip flights between San Jose and Chicago start at $210 from Thu, May 28 to Fri, Jun 5.
To book business class trips from San Jose to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between San Jose and Chicago starts at $444 from Fri, Apr 24 to Mon, Apr 27 with Frontier.
The cheapest last-minute deal between San Jose and Chicago at price $444 is offered by Frontier from Fri, Apr 24 to Mon, Apr 27.
To find last-minute flight deals from San Jose to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

Search more flights

Popular trips from San Jose

  1. Seattle
    $225
    May 23 — May 29
    1 stop 5 hr 38 min Frontier
  2. Tokyo
    $562
    Apr 30 — May 6
    Nonstop 11 hr 10 min ZIPAIR Tokyo
  3. Honolulu
    $332
    May 4 — May 11
    1 stop 5 hr 35 min Alaska
  4. Los Angeles
    $103
    May 29 — Jun 5
    Nonstop 1 hr 23 min Frontier

Find cheap flights from San Jose to anywhere

Find cheap flights on popular routes