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Cheap flights from San Jose (SJC) to Midway (MDW) from $88

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
SJC — MDW
Jun 14 — Jun 211
From?
To?
Fri 6/14
Fri 6/21
1 adult, Economy
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Cheap flight deals from San Jose to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 9, 2024.

Popular in

June

Cheapest in

December

Round-trip from

$222

One-way from

$206
High demand for flights, 48% potential price rise
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Best time to find cheap flights, 64% potential price drop
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From San Jose to Chicago Midway
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One-way flight from San Jose to Chicago Midway
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What is the cheapest day to fly round-trip from San Jose to Chicago Midway Airport?

Flights from San Jose to Chicago Midway Airport are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago Midway Airport.

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 60 days in advance, which can save you up to 431% on flights from San Jose to Chicago Midway Airport compared to booking the week you need them. Waiting 60 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 $201. For sooner than that we have options available in the next 3 days from $587.

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

Our data shows that October tends to be the cheapest month to fly to Chicago Midway Airport from San Jose. Users have commonly found prices around $412 for the month, but tickets can be as low as $126. Due to multiple factors, prepare for potentially higher prices in March.

What is the cheapest time of day to fly from SJC to MDW?

A simple way to save on the total cost of your ticket is to fly from San Jose to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 32% on your trip compared to booking a flight at noon.

Cheap San Jose to Midway flights in June & July 2024

Find cheap flight options from San Jose to Midway specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,020,828 searches. Prices were last updated on June 9, 2024.
Check out some of the best flight deals from San Jose to Chicago in 2024. More deals are always being added, so be sure to check back regularly.
Thu 7/2512:51 pmSJC - MDW
1 stop7h 09mFrontier
Sun 7/286:00 amMDW - SJC
1 stop13h 25mFrontier
Deal found 6/8$261
Mon 7/2211:30 amSJC - MDW
1 stop27h 40mFrontier
Fri 8/26:15 amMDW - SJC
1 stop13h 26mFrontier
Deal found 6/8$297
Thu 7/2512:51 pmSJC - MDW
1 stop7h 09mFrontier
Mon 7/296:15 amMDW - SJC
1 stop12h 42mFrontier
Deal found 6/8$322
Mon 7/2211:30 amSJC - MDW
1 stop27h 40mFrontier
Fri 8/24:06 pmMDW - SJC
2 stops19h 05mFrontier
Deal found 6/8$350
Tue 7/3011:30 amSJC - MDW
1 stop7h 20mFrontier
Wed 8/76:15 amMDW - SJC
1 stop13h 30mFrontier
Deal found 6/8$355
Tue 7/3011:30 amSJC - MDW
1 stop7h 20mFrontier
Sun 8/46:00 amMDW - SJC
1 stop13h 25mFrontier
Deal found 6/8$386
Thu 7/2512:51 pmSJC - MDW
1 stop7h 09mFrontier
Mon 7/294:03 pmMDW - SJC
2 stops27h 42mFrontier
Deal found 6/7$400
Tue 7/166:15 amSJC - MDW
1 stop5h 54mDelta
Wed 7/312:49 pmMDW - SJC
1 stop7h 42mDelta
Deal found 6/8$402
Wed 7/248:15 pmSJC - MDW
2 stops10h 38mDelta
Wed 7/312:49 pmMDW - SJC
1 stop7h 42mDelta
Deal found 6/9$431

San Jose to Midway 2024 flight deals

Discover exclusive flight deals for travel between San Jose and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 9, 2024.
Check out some of the best flight deals from San Jose to Chicago in 2024. More deals are always being added, so be sure to check back regularly.
Sat 8/3111:31 amSJC - MDW
1 stop22h 21mFrontier
Sat 9/710:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 6/8$177
Wed 8/2110:20 pmSJC - MDW
1 stop6h 13mFrontier
Sat 8/2411:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 6/9$180
Wed 8/2110:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 8/256:00 amMDW - SJC
1 stop13h 25mFrontier
Deal found 6/9$184
Wed 8/2110:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 8/256:00 amMDW - SJC
1 stop13h 25mFrontier
Deal found 6/9$188
Thu 8/1510:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 8/256:00 amMDW - SJC
1 stop13h 25mFrontier
Deal found 6/8$189
Thu 8/2212:51 pmSJC - MDW
1 stop21h 01mFrontier
Mon 8/2610:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 6/7$190
Fri 8/911:30 amSJC - MDW
1 stop23h 33mFrontier
Mon 8/126:15 amMDW - SJC
1 stop12h 42mFrontier
Deal found 6/8$208
Sat 8/1011:31 amSJC - MDW
1 stop8h 29mFrontier
Wed 8/1410:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 6/8$222
Wed 9/1110:20 pmSJC - MDW
1 stop6h 13mFrontier
Mon 10/711:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 6/7$229

San Jose to Midway flights leaving soon

Find last-minute flight options from San Jose to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 9, 2024.
Book one of these great deals on flights from San Jose to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
Sat 6/156:15 amSJC - MDW
2 stops8h 49mDelta
Tue 6/259:34 amMDW - SJC
2 stops8h 35mDelta
Deal found 6/8$762
Tue 6/1812:26 pmSJC - MDW
1 stop7h 20mDelta
Thu 6/203:45 pmMDW - SJC
1 stop8h 57mDelta
Deal found 6/8$802
Tue 6/1812:26 pmSJC - MDW
1 stop7h 20mDelta
Thu 6/209:34 amMDW - SJC
2 stops8h 35mDelta
Deal found 6/8$807
Sat 6/156:15 amSJC - MDW
2 stops8h 49mDelta
Mon 6/1712:45 pmMDW - SJC
1 stop9h 12mDelta
Deal found 6/8$827
Sat 6/156:15 amSJC - MDW
2 stops8h 49mDelta
Mon 6/179:34 amMDW - SJC
2 stops9h 50mDelta
Deal found 6/8$832
Sat 6/156:15 amSJC - MDW
2 stops8h 49mDelta
Tue 6/253:45 pmMDW - SJC
1 stop8h 57mDelta
Deal found 6/8$842
Sun 6/166:30 amSJC - MDW
1 stop9h 29mDelta
Tue 6/259:34 amMDW - SJC
2 stops8h 35mDelta
Deal found 6/8$905
Sun 6/166:15 amSJC - MDW
2 stops8h 49mDelta
Tue 6/259:34 amMDW - SJC
2 stops11h 10mDelta
Deal found 6/8$910
Fri 6/146:30 amSJC - MDW
1 stop9h 29mDelta
Mon 6/172:24 pmMDW - SJC
1 stop8h 13mDelta
Deal found 6/8$945

One-way flights to Midway from San Jose

Search for one-way flight options from San Jose to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 9, 2024.
Some of the best available deals we've found on one-way flights from San Jose to Chicago. Those needing a return flight from San Jose to Chicago can use the search form above.
Fri 8/2310:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 6/9$88
Mon 8/1910:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 6/7$90
Tue 9/310:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 6/8$95
Tue 8/1310:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 6/8$98
Sat 8/3111:31 amSJC - MDW
1 stop22h 21mFrontier
Deal found 6/8$101
Tue 7/2311:30 amSJC - MDW
1 stop7h 20mFrontier
Deal found 6/8$108
Sat 8/311:31 amSJC - MDW
1 stop8h 29mFrontier
Deal found 6/8$110
Mon 7/2211:30 amSJC - MDW
1 stop27h 40mFrontier
Deal found 6/8$113
Fri 8/911:30 amSJC - MDW
1 stop23h 33mFrontier
Deal found 6/8$124

Find flights from San Jose to Midway within your budget

Customize your flight search to find flights from San Jose to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 9, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$177 - $669

Route

Depart

Return

Price

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Sat 8/31

1 stop22h 21m

Chicago Midway

Sat 9/7

1 stop20h 51m

$177

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Fri 8/23

1 stop6h 13m

Chicago Midway

Mon 8/26

1 stop12h 57m

$180

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Wed 8/21

1 stop6h 13m

Chicago Midway

Sun 8/25

1 stop13h 25m

$184

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Wed 8/21

1 stop6h 13m

Chicago Midway

Sun 8/25

1 stop13h 25m

$188

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Thu 8/15

1 stop6h 13m

Chicago Midway

Sun 8/25

1 stop13h 25m

$189

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Thu 8/22

1 stop21h 01m

Chicago Midway

Mon 8/26

1 stop20h 51m

$190

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Tue 8/27

1 stop7h 53m

Chicago Midway

Wed 9/4

2 stops13h 12m

$313

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Tue 8/27

2 stops12h 21m

Chicago Midway

Wed 9/4

2 stops13h 12m

$318

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Thu 6/20

3 stops35h 18m

Chicago Midway

Sun 6/23

3 stops41h 35m

$669

Flights are sorted by cheapest first

Deals found on 6/8

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

Use this chart to determine the cheapest time to fly round-trip from San Jose to Midway. Price data was last updated on June 9, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their San Jose to Chicago Midway Airport flight should consider departing on Saturday mornings when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from San Jose to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San Jose with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Midway by month

Plan your trip to Midway by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated June 9, 2024.
Peruse reviews from past customers who have flown with Frontier, Delta and Volaris from San Jose to Chicago to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,310 reviews

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Boarding

8.2

Food

7.4

Reviews

1 / 10

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Delta
8.0
Very good
10,310 reviews
Delta
8.0
Very good
10,310 reviews

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Boarding

8.2

Food

7.4

Reviews

1 / 10

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Volaris
6.6
Okay
1,457 reviews
Delta
8.0
Very good
10,310 reviews

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Boarding

8.2

Food

7.4

Reviews

1 / 10

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Frontier
6.2
Okay
3,975 reviews
Delta
8.0
Very good
10,310 reviews

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Boarding

8.2

Food

7.4

Reviews

1 / 10

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Related info for your journey

Find useful and relevant information for your journey from San Jose to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 5 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 3 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.

  • Can I find flights from San Jose to Chicago Midway Airport for under $200 on Cheapflights?

    Yes, there are multiple flights from San Jose to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Frontier for just $177, but on average you can expect to pay $238.

  • Are there last-minute flights available from San Jose to Chicago Midway Airport for under $800?

    There are currently 20+ open flights from San Jose to Chicago Midway Airport within the next 7 days for less than $800.

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

    Frontier, at $177, was found to be the cheapest airline from San Jose to Chicago Midway Airport. An alternate airline flying to your destination would be Delta. Users have found that Frontier is 54% cheaper than the other options available to this destination.

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

    Looking at all options, your cheapest flight can be booked for $405. While the most popular route (San Jose - Chicago Midway) can be booked for $180 on average our data indicates $419 when flying from San Jose to Chicago Midway Airport.

  • What does SJC to MDW mean?

    SJC and MDW are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. SJC to MDW refers to a flight route from San Jose Airport to Chicago Midway Airport.

  • Can I find deals for flights from San Jose to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your San Jose to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from San Jose to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter San Jose to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from San Jose to Midway that include hotel bookings?

    Yes. In addition to deals on San Jose to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Midway.

  • Can I find deals for business class flights from San Jose to Midway?

    Yes. Cheapflights offers flight deals from San Jose to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from San Jose to Midway that allow pets onboard?

    Many airlines flying from San Jose to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from San Jose to Midway?

    Yes, you can often find last-minute deals on San Jose to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the San Jose to Chicago Midway Airport flight deals updated?

    The San Jose to Chicago Midway Airport flight deals you see on this page were last updated on 6/9.

  • 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 Delta, Frontier or United Airlines as they are the most popular for this route.

  • What is the cheapest month to book a flight from San Jose to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from San Jose to Chicago Midway Airport (average of $141). Flying from San Jose to Chicago Midway Airport in July is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for San Jose to Midway
See prices for flight routes from nearby airports that may be better suited for you.

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Top 3 airlines flying from San Jose to Midway

Discover the top 3 airlines that operate flights from San Jose to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 9, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$207FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$203Average$459FlexibilityNo cancel feeOn-time69%
DeltaCheapest$384Average$580FlexibilityNo cancel feeOn-timeN/A
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Boston to New York flights
Detroit to Los Angeles flights
Chicago to New York flights
Cincinnati to Miami flights
Orlando to Tampa flights
Newark Airport to San Juan flights
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New Orleans to Atlanta flights
San Jose to Mendoza flights

Search flights from San Jose to Midway by cabin class

Find flights from San Jose to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from San Jose to Midway

Find hourly flight availability from San Jose to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 9, 2024.
34%of flight departuresEarly morningMidnight to 6 am
50%of flight departuresMorning6 am to noon
16%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

Explore weekly flight availability from San Jose to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 9, 2024.
Sunday2daily flights
Monday7daily flights
Tuesday6daily flights
Wednesday6daily flights
Thursday7daily flights
Friday7daily flights
Saturday2daily flights

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