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

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

SJC - MDW
Price
$205 - $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

July

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

Round-trip from

$205

From San Jose to Chicago Midway

One-way from

$199

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.
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 20 days early can save you up to 10% on average compared to booking a flight this week. If booking 20 days before your flight isn’t an option for you, users have found flights from San Jose to Chicago Midway for as little as $137 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 $157 for flights departing within the next 3 days.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago Midway. Flights to Chicago Midway from San Jose in April are about $135 on average during April, but can be found for as low as $33.

Cheap flights from San Jose to Chicago Midway in April, May 2021

30 Apr - 5 May
$271pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose
15 May - 22 May
$272pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose
20 May - 25 May
$281pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose

San Jose to Chicago Midway 2021 flight deals

30 Apr - 5 May
$271pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose
15 May - 22 May
$272pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose
20 May - 25 May
$281pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose

Last minute flights from San Jose to Chicago Midway

21 Apr - 2 May
$399pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose
22 Apr - 26 Apr
$424pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose
22 Apr - 27 Apr
$482pp
SJC
San Jose
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
SJC
San Jose

One-way flights to Chicago Midway from San Jose

2:15 am - 10:40 am
Delta
1 Stop
6h 25m
SJC - MDW
Delta
$199
Delta
2:15 am - 1:02 pm
Delta
1 Stop
8h 47m
SJC - MDW
Delta
$229
Delta
8:45 am - 7:20 pm
Delta
1 Stop
8h 35m
SJC - MDW
Delta
$238
Delta

Related info for your journey

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.

What safety measures are being taken by airlines flying from San Jose to Chicago Midway to control the spread of COVID-19?

New policies can now be found on Alaska Airlines and Delta to help keep travelers safe while flying. Some of the new policies that have been implemented to accommodate travelers flying from San Jose to Chicago Midway are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

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 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 $271, but on average you can expect to pay $328.

Are there nonstop flights from San Jose to Chicago Midway for under $300 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.

Are there last-minute flights available from San Jose to Chicago Midway for under $400?

There are currently 12+ open flights from San Jose to Chicago Midway within the next 7 days for less than $400.

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 1 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 is the flight from San Jose to Chicago Midway?

A quick flight from San Jose to Chicago Midway can take about 6h 25m. Delta provides one of the quickest options available for as low as $331.

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

Delta, at $271, was found to be the cheapest airline from San Jose to Chicago Midway.. Delta is 33% 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?

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $132.

Alternative routes for San Jose to Chicago Midway

Destination information for Chicago Midway

Average temperature for April in Chicago Midway
62.6 °F
Avg rainfall for April in Chicago Midway
2.3 ″

Airports servicing San Jose

Airports servicing Chicago

Top 5 airlines flying from San Jose to Chicago Midway

Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$155 $265 No cancel fee 65%
American Airlines
$251 $388 No cancel fee 71%
United Airlines
$129 $388 No cancel fee 69%
Delta
$295 $507 No cancel fee N/A
Southwest
$404 $628 No cancel fee 63%

Hourly flight availability from San Jose to Chicago Midway

Morning 6 AM to noon 75% of SJC to MDW departures
Afternoon Noon to 6 PM 25% of SJC to MDW departures
Early morning Midnight to 6 AM 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
1 daily flight
Monday
3 daily flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
1 daily flight
Friday
1 daily flight
Saturday
0 flights
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