Midway

Cheap flights from San Jose to Chicago (SJC - MDW)

How to find the cheapest flight from San Jose to Midway

All the information you need to plan the best SJC to MDW flight in 2022: compare San Jose to Midway flight prices with the expected peak season, weather and rainfall in Midway.

SJC - MDW

Price

$205 - $646

MDW

Temperature

23 - 73.4 °F

MDW

Precipitation

1.7 - 4.9 inches

Popular in

September

High demand for flights, 37% potential price rise

Cheapest in

July

Best time to find cheap flights, 49% potential price drop

Round-trip from

$205

From San Jose to Chicago Midway

One-way from

$148

One-way flight from San Jose to Chicago Midway

How far in advance should I book a flight from San Jose to Chicago Midway Airport?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 24 days in advance, which can save you up to 48% on flights from San Jose to Chicago Midway Airport compared to booking the week you need them. Waiting 24 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $378. For sooner than that we have options available in the next 3 days from $526.

What is the cheapest month to fly from San Jose to Chicago Midway Airport?

Our data shows that July tends to be the cheapest month to fly to Chicago Midway Airport from San Jose. Users have commonly found prices around $329 for the month, but tickets can be as low as $167. Due to multiple factors, prepare for potentially higher prices in December.

When is the cheapest time to fly from San Jose to Chicago Midway Airport (SJC - MDW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Jose to Chicago Midway Airport as you normally would.

Cheap flights from San Jose to Midway in January, February 2022

The best prices found for SJC to MDW flights for January, February
Feb 11 - Feb 15
SJC

San Jose

MDW

Chicago Midway

2 stops

14h 10m
MDW

Chicago Midway

SJC

San Jose

2 stops

13h 27m
$273

Delta

View Deal

Deal found 1/18/22

Feb 5 - Feb 7
SJC

San Jose

MDW

Chicago Midway

1 stop

8h 35m
MDW

Chicago Midway

SJC

San Jose

2 stops

12h 56m
$284

Delta

View Deal

Deal found 1/17/22

Feb 11 - Feb 15
SJC

San Jose

MDW

Chicago Midway

1 stop

9h 22m
MDW

Chicago Midway

SJC

San Jose

2 stops

12h 56m
$294

Delta

View Deal

Deal found 1/18/22

San Jose to Midway 2022 flight deals

Cheap flights to Midway from San Jose found for this year
Feb 11 - Feb 15
SJC

San Jose

MDW

Chicago Midway

2 stops

14h 10m
MDW

Chicago Midway

SJC

San Jose

2 stops

13h 27m
$273

Delta

View Deal

Deal found 1/18/22

Feb 5 - Feb 7
SJC

San Jose

MDW

Chicago Midway

1 stop

8h 35m
MDW

Chicago Midway

SJC

San Jose

2 stops

12h 56m
$284

Delta

View Deal

Deal found 1/17/22

Feb 11 - Feb 15
SJC

San Jose

MDW

Chicago Midway

1 stop

9h 22m
MDW

Chicago Midway

SJC

San Jose

2 stops

12h 56m
$294

Delta

View Deal

Deal found 1/18/22

Last minute flights from San Jose to Midway

Late deals on return flights to Midway from San Jose, departing today and this week
Jan 26 - Feb 4
SJC

San Jose

MDW

Chicago Midway

1 stop

7h 33m
MDW

Chicago Midway

SJC

San Jose

2 stops

10h 19m
$445

Delta

View Deal

Deal found 1/19/22

Jan 26 - Jan 30
SJC

San Jose

MDW

Chicago Midway

1 stop

7h 33m
MDW

Chicago Midway

SJC

San Jose

2 stops

11h 45m
$550

Delta

View Deal

Deal found 1/18/22

Jan 27 - Jan 28
SJC

San Jose

MDW

Chicago Midway

1 stop

7h 33m
MDW

Chicago Midway

SJC

San Jose

2 stops

8h 37m
$570

Delta

View Deal

Deal found 1/19/22

One-way flights to Chicago Midway from San Jose

The cheapest one-way flights from San Jose to Midway
Feb 11
SJC

San Jose

MDW

Chicago Midway

2 stops

9h 53m
$137

Delta

View Deal

Deal found 1/18/22

Feb 5
SJC

San Jose

MDW

Chicago Midway

1 stop

7h 33m
$148

Delta

View Deal

Deal found 1/17/22

Feb 5
SJC

San Jose

MDW

Chicago Midway

2 stops

8h 16m
$153

Delta

View Deal

Deal found 1/17/22

Related info for your journey

Useful info, stats and facts about San Jose to Midway flights.

What airport do you fly from for flights from San Jose to Chicago Midway?

San Jose (SJC) is the airport you will fly out of if you book a flight from San Jose to Chicago Midway. You should not have trouble finding flights to Chicago Midway from San Jose; the airport handles an average of 2 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 6 airlines have flights from the San Jose airport to Chicago Midway. It is only a 2.9 mi journey to San Jose (SJC) from San Jose’s city center.

Which airlines flying from San Jose to Chicago Midway have flexible cancellations due to COVID-19?

Delta, United Airlines, and American Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from San Jose to Chicago Midway Airport for under $300 on Cheapflights?

Yes, there are multiple flights from San Jose to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Delta for just $273, but on average you can expect to pay $358.

Are there last-minute flights available from San Jose to Chicago Midway Airport for under $500?

There are currently 7+ open flights from San Jose to Chicago Midway Airport within the next 7 days for less than $500.

What are the cheapest airlines flying from San Jose to Chicago Midway Airport round-trip?

Delta, at $273, was found to be the cheapest airline from San Jose to Chicago Midway Airport. An alternate airline flying to your destination would be Frontier. Users have found that Delta is 32% cheaper than the other options available to this destination.

What are the most popular airlines that fly from San Jose to Chicago Midway Airport?

When booking a flight from San Jose to Chicago Midway Airport, you may want to consider flying on American Airlines, Alaska Airlines or Delta as they are the most popular for this route.

What are the cheapest flights from San Jose to Chicago Midway Airport?

Looking at all options, your cheapest flight can be booked for $240. While the most popular route (San Jose - Chicago Midway) can be booked for $284 on average our data indicates $240 when flying from San Jose to Chicago Midway Airport.

Can I fly to Chicago Midway from San Jose right now?

Information is based on travel restrictions for travel to Chicago Midway within the United States

Most visitors from San Jose need to provide a negative COVID-19 test result and/or quarantine to enter Chicago Midway.

COVID-19 testing requirements
Visitors from San Jose must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago Midway.

Quarantine requirements
Visitors from San Jose are not required to quarantine after entering Chicago Midway.

Can I fly back to San Jose from Chicago Midway?

Returning to San Jose from Chicago Midway

COVID-19 testing requirements
Visitors from Chicago Midway must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to San Jose.

Quarantine requirements
Visitors from Chicago Midway are not required to quarantine after entering San Jose.

Alternative routes for San Jose to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from San Jose to Midway

The chart below displays the airlines Cheapflights users traveling from San Jose to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
United Airlines
Cheapest$129
Average$388
FlexibilityNo cancel fee
On-time69%
COVID-19 safety
Spirit Airlines
Cheapest$155
Average$265
FlexibilityNo cancel fee
On-time65%
COVID-19 safety
American Airlines
Cheapest$251
Average$388
FlexibilityNo cancel fee
On-time71%
COVID-19 safety
Delta
Cheapest$295
Average$507
FlexibilityNo cancel fee
On-timeN/A
COVID-19 safety
Southwest
Cheapest$404
Average$628
FlexibilityNo cancel fee
On-time63%
COVID-19 safety

Hourly flight availability from San Jose to Midway

See what time of day planes typically take off from San Jose to Midway
3%of flight departuresEarly morningMidnight to 6 am
82%of flight departuresMorning6 am to noon
15%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from San Jose to Midway

See how many times per day planes take to the skies headed from San Jose to Midway
Sunday3daily flights
Monday3daily flights
Tuesday3daily flights
Wednesday3daily flights
Thursday3daily flights
Friday3daily flights
Saturday0daily flights