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

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The best prices from San Jose to Chicago Midway are usually found in March or November, booked 60 days in advance, depart on a Tuesday or Sunday and return on a Thursday

Home North America USA Illinois Chicago Chicago Midway Cheap flights from San Jose to Chicago Midway

How to find the cheapest flight from
San Jose (SJC) to Chicago Midway (MDW)

SJC - MDW
Price
$316 - $646
MDW
Temperature
33.8 - 84.2 °F
MDW
Rainfall
0.7 - 4.3 inches
Popular in September High demand for flights, 37% potential price rise
Cheapest in March Best time to find cheap flights, 23% potential price drop
Round-trip from $316 From San Jose to Chicago Midway
One-way from $123 One-way flight from San Jose to Chicago Midway
Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from San Jose to Chicago Midway?

Travelers have found that booking a Monday departure is the best way to save up to 48% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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

Users have found that booking a flight from San Jose to Chicago Midway at least 37 days early can save you up to 10% on average compared to booking a flight this week. If booking 37 days before your flight isn’t an option for you, users have found flights from San Jose to Chicago Midway for as little as $177 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $177 for flights departing within the next 3 days.

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

It’s optimal to fly from San Jose to Chicago Midway in the afternoon. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the noon.

San Jose to Chicago Midway 2020 flight deals

Cheap flights to Chicago Midway from San Jose found for this year
27 Oct - 28 Oct
$245pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SJC
San Jose
21 Sep - 22 Sep
$246pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose
27 Sep - 30 Sep
$256pp
SJC
San Jose
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SJC
San Jose

One-way flights to Chicago Midway from San Jose

The cheapest one-way flights from San Jose to Chicago Midway
7:25 am - 3:11 pm
Delta
1 Stop
5h 46m
SJC - MDW
Delta
$123
Delta
2:20 am - 12:30 pm
Delta
1 Stop
8h 10m
SJC - MDW
Delta
$133
Delta
1:45 pm - 6:53 am
Multiple Airlines
2 Stops
39h 08m
SJC - MDW
Multiple Airlines
$404
Kiwi.com

Related info for your journey

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

Flight FAQs

From San Jose to Chicago Midway

Are flight prices decreasing from San Jose to Chicago Midway due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both San Jose and Chicago Midway for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

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

Yes, there are multiple flights from San Jose to Chicago Midway for under $300. The cheapest flight booked recently is on Delta for just $245, but on average you can expect to pay $477.

Are there nonstop flights from San Jose to Chicago Midway for under $200 on Cheapflights?

There are no nonstop flights from San Jose to Chicago Midway, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Does it rain more in San Jose or Chicago Midway?

When traveling, we recommend packing in preparation to handle common weather conditions. The rainfall in San Jose is typically less than Chicago Midway. We can gather that this will continue over the next 0 days.

Is San Jose weather warmer or cooler than Chicago Midway?

You can imagine temperatures to be in the 84 °F range in July. The weather in Chicago Midway is generally hotter than San Jose's. As flight availability is subject to become more limited as peak season approaches it is ideal to book in a timely manner.

How long does is the flight from San Jose to Chicago Midway?

For as low as $814, Delta can have you in Chicago Midway from San Jose in 5h 46m.

What is the cheapest airline to fly from San Jose to Chicago Midway round-trip?

Flying on Delta is currently your cheapest option to Chicago Midway, with prices starting at $245. Delta is 40% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from San Jose to Chicago Midway one-way?

For one-way options, check prices for Delta. According to our data, you can fly for as low as $123.

Related searches

Flights to Chicago Midway from San Jose
Flights to San Jose Flights to Chicago Midway Flights from San Jose Flights from Chicago Midway

Rent a Car

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Alternative routes for San Jose to Chicago Midway

Los Angeles to Chicago from $218 pp
Long Beach to Chicago from $258 pp
Burbank to Chicago from $304 pp
Fresno to Chicago from $362 pp
Bakersfield to Chicago from $1016 pp

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from San Jose to Chicago Midway
Average temperature for August in Chicago Midway
82.4 °F
Avg rainfall for August in Chicago Midway
3.9 ″

Airports servicing San Jose

San Jose (SJC)

Airports servicing Chicago

Chicago Midway (MDW)

Popular flight searches

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Hourly flight availability from San Jose to Chicago Midway

Morning 6 AM to noon 100% of SJC to MDW departures
Early morning Midnight to 6 AM 0% of SJC to MDW departures
Afternoon Noon to 6 PM 0% of SJC to MDW departures
Evening 6 PM to midnight 0% of SJC to MDW departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from San Jose to Chicago Midway
Sunday
2 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
2 daily flights
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