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Cheap flights from San Jose to Chicago Midway

Compare San Jose to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from San Jose to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from San Jose to Chicago Midway Airport? If you want to travel next month, return fares start from P20,090. Find the lowest prices on one-way and return tickets right here.
Chicago.P8,222 per passenger.Departing Tue, 19 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Jose International on Tue, 19 May, arriving in Chicago Midway.Price includes taxes and charges.From P8,222, select.
Chicago.P8,222 per passenger.Departing Tue, 2 Jun.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Jose International on Tue, 2 Jun, arriving in Chicago Midway.Price includes taxes and charges.From P8,222, select.
Chicago.P8,527 per passenger.Departing Wed, 29 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Jose International on Wed, 29 Apr, arriving in Chicago Midway.Price includes taxes and charges.From P8,527, select.
Chicago.P8,821 per passenger.Departing Tue, 21 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Tue, 21 Apr, arriving in Chicago Midway.Price includes taxes and charges.From P8,821, select.
Chicago.P8,833 per passenger.Departing Tue, 2 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Tue, 2 Jun, arriving in Chicago Midway.Price includes taxes and charges.From P8,833, select.
Chicago.P8,833 per passenger.Departing Tue, 19 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Tue, 19 May, arriving in Chicago Midway.Price includes taxes and charges.From P8,833, select.
Chicago.P12,156 per passenger.Departing Mon, 3 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Mon, 3 Aug, arriving in Chicago Midway.Price includes taxes and charges.From P12,156, select.
Chicago.P12,156 per passenger.Departing Thu, 30 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Thu, 30 Jul, arriving in Chicago Midway.Price includes taxes and charges.From P12,156, select.
Chicago.P12,172 per passenger.Departing Tue, 1 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From P12,172, select.
Chicago.P13,975 per passenger.Departing Thu, 8 Oct.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Jose International on Thu, 8 Oct, arriving in Chicago Midway.Price includes taxes and charges.From P13,975, select.
Chicago.P16,683 per passenger.Departing Thu, 8 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Thu, 8 Oct, arriving in Chicago Midway.Price includes taxes and charges.From P16,683, select.
Chicago.P23,862 per passenger.Departing Sun, 29 Mar.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Jose International on Sun, 29 Mar, arriving in Chicago Midway.Price includes taxes and charges.From P23,862, select.
Chicago.P27,469 per passenger.Departing Sun, 29 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Jose International on Sun, 29 Mar, arriving in Chicago Midway.Price includes taxes and charges.From P27,469, select.

Find the cheapest month to fly from San Jose to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Jose to Chicago Midway flights are currently cheapest in May.
Mar
from P23,862
Apr
from P8,527
May
from P8,222
Jun
from P8,222
Jul
from P12,156
Aug
from P12,156
Sep
from P12,172
Oct
from P13,975
Nov
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Dec
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Jan
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Feb
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Direct flights from San Jose to Chicago Midway

San Jose to Chicago Midway: Alternative routes

Compare routes from San Jose to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
Closest
from P8,222
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Chicago O'Hare International

25km from central Chicago
Cheapest
from P4,780
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Chicago Dupage County

51km from central Chicago
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Chicago Rockford

126km from central Chicago
from P16,119
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San Jose to Chicago: Flight information

The things to know before you go.
Cheapest flight foundP8,222
Cheapest month to flyMay
Average flight time4 hrs, 5 mins
Most popular airlineSouthwest Airlines
Average flights per week15

Finding cheap flights from San Jose to Chicago Midway: Frequently asked questions

The best price we found for a return flight from San Jose to Chicago Midway is P16,399. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 5 minutes is the average flight time from San Jose to Chicago Midway.
Southwest Airlines flies direct from San Jose to Chicago Midway.
As of March 2026, there are 15 flights per week flying from San Jose to Chicago Midway.
The cheapest month to fly from San Jose to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from San Jose to Chicago Midway Airport on Tuesday, 19 May 2026.
Yes – the average flight time is 4 hours and 5 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Flying from San Jose to Chicago Midway International Airport (MDW): What you need to know

  • San Jose's main airport is Norman Y. Mineta San Jose International Airport (SJC). Explore your departure options from here when searching for your flights from San Jose to Chicago Midway International Airport (MDW).

  • The average duration of a direct San Jose to Chicago Midway International Airport flight is 4 hours 10 minutes.

  • Chicago Midway International Airport is located in Chicago. The city operates on the UTC-5 timezone and is two hours ahead of San Jose.

  • The busiest route is from Norman Y. Mineta San Jose International Airport (SJC) to Chicago Midway International Airport (MDW). There are 7 direct services every week. Southwest Airlines operates a 6:35am departure between SJC and MDW.

  • Leave plenty of time to get on your flight from San Jose to MDW. Generally, it's best to arrive two hours before international departures and an hour ahead for domestic flights.

  • Longer lines at security and check-in are likely if you're heading away during high season, so give yourself even more breathing space. The recommendation for peak times? Arrive up to four hours ahead for international flights and two hours for domestic departures.

Airports in San Jose

Norman Y. Mineta San Jose International Airport (SJC)

  • Norman Y. Mineta San Jose International Airport (SJC) provides a hassle-free way to reach your destination. Nonstop flights from San Jose to Chicago Midway International Airport (MDW) take off from this terminal.

  • When taking off from SJC, you can catch a direct flight from San Jose to Chicago Midway International Airport with Southwest Airlines.

  • The top choice among passengers flying between SJC and MDW is Southwest Airlines.

  • Southwest Airlines is the most punctual carrier. An impressive 88.52% of its departures on this route arrive as planned.

  • Located around 6 kilometres from the centre of San Jose, SJC can be reached in about 10 minutes by car (depending on traffic). The journey on public transport takes roughly 45 minutes.

  • Planning to catch an early flight from San Jose to Chicago Midway International Airport? Avoid rushing to the terminal (and enjoy a few extra z's) by choosing one of these hotels close to Norman Y. Mineta San Jose International Airport:

  • 84.69% of flights leaving Norman Y. Mineta San Jose International Airport land at their destination as planned. With its strong performance rating, disruptions are unlikely when setting off from SJC.

  • SJC is located at 1701 Airport Boulevard, Suite B-1130.

About Chicago Midway International Airport (MDW)

  • Have a late flight from San Jose to Chicago Midway International Airport? Don't let it hijack your sleep schedule. Stay at one of these hotels near MDW and give yourself a well-earned lights-out:

  • Travel at your own pace with a Chicago Midway International Airport rental car. Book your wheels from Dollar, Hertz or Budget and discover more of Chicago and beyond.

  • To secure the lowest price, reserve your ride around four weeks ahead of your San Jose to Chicago Midway International Airport flight.

  • You'll find MDW at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Chicago Midway International Airport to central Chicago is roughly 14 kilometres. If you're getting a cab or renting a car, do some research to make your trip as easy as possible. Journey times can vary depending on traffic conditions and the time of day.

  • It'll take around 45 minutes if you're travelling on public transport.

How to find the cheapest flights from San Jose to Chicago Midway International Airport (MDW)

  • The lowest price we've found for a one-way ticket from San Jose to Chicago Midway International Airport is P8,222. For a return flight on this route, the best price is P16,399. Depending on when you want to go and the availability, these fares may change.

  • Booking early is often the key to finding a cheap flight from San Jose to MDW. Airlines adjust prices based on demand, so the closer you get to departure, the more you'll likely spend.

  • Affordable San Jose to Chicago Midway International Airport tickets are easier to find when you have flexibility in your schedule. Use the 'Whole month' search tool to compare fares across every month and then pick the cheapest day.

  • There's no need to check back in every day to find out if prices have dropped when you create a Price Alert. We'll let you know the moment a better deal comes up on plane tickets from San Jose to MDW.

  • Tailor your travel plans using filters. Choose your ideal departure and arrival times, airlines and total journey duration. You can also sort the results by 'Cheapest,' 'Best' or 'Fastest' flights from San Jose to Chicago Midway International Airport.

The best time to fly from San Jose to Chicago Midway International Airport (MDW)

  • July is the most popular month for flights from San Jose to Chicago Midway International Airport (MDW). Plan your visit to Chicago in May if you'd rather be there when it's quieter.

  • When booking your San Jose to MDW plane ticket, consider what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January sees temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from San Jose to Chicago Midway International Airport around that time if you want to travel in cooler conditions.

More about Chicago

Explore more of the United States

  • You've seen Chicago, now it's time to explore more of the United States. Journey around 257 kilometres south-east to Indianapolis to check off its leading sights. From 9-11 Memorial to Lucas Oil Stadium and Eiteljorg Museum, you've got a jam-packed schedule ahead.

  • Milwaukee is another must-experience destination in the United States and is around 137 kilometres north of Chicago. No trip is complete without a visit to Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

Plan the rest of your trip from San Jose to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.