Cheap flights from San Jose (SJC) to Midway (MDW) from $95
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 9/3. 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 2 — Jun 91
From?
To?
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 May 28, 2024.
Popular in | June |
|---|---|
Cheapest in | December |
Average price | $426 |
Round-trip from | $222 |
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 $414 for the month, but tickets can be as low as $126. Due to multiple factors, prepare for potentially higher prices in March.
When is the cheapest time to fly from San Jose to Chicago Midway Airport (SJC - 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 Delta flights from San Jose to Midway
Explore cheap flight options specifically provided by Delta for the route between San Jose and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
Consider these cheap Delta flights we've found departing from San Jose to Chicago. Make sure to check back often as deals are often changing.
Sat 9/1412:05 pmSJC - MDW
1 stop7h 39mDelta
Wed 9/182:00 pmMDW - SJC
1 stop8h 39mDelta
Deal found 5/28$328
Sat 9/1412:05 pmSJC - MDW
1 stop7h 39mDelta
Wed 9/181:10 pmMDW - SJC
2 stops11h 22mDelta
Deal found 5/28$333
Tue 10/86:50 amSJC - MDW
1 stop9h 09mDelta
Tue 10/152:00 pmMDW - SJC
1 stop8h 39mDelta
Deal found 5/27$340
Tue 10/86:30 amSJC - MDW
2 stops9h 35mDelta
Tue 10/152:00 pmMDW - SJC
1 stop8h 39mDelta
Deal found 5/28$345
Tue 10/86:30 amSJC - MDW
2 stops9h 35mDelta
Tue 10/151:10 pmMDW - SJC
2 stops11h 22mDelta
Deal found 5/28$350
Sat 9/286:30 amSJC - MDW
2 stops8h 33mDelta
Mon 10/71:05 pmMDW - SJC
1 stop8h 03mDelta
Deal found 5/28$353
Fri 8/167:00 pmSJC - MDW
2 stops11h 38mDelta
Mon 8/191:24 pmMDW - SJC
2 stops10h 35mDelta
Deal found 5/27$358
Tue 10/86:50 amSJC - MDW
1 stop9h 09mDelta
Fri 10/1810:11 amMDW - SJC
1 stop10h 57mDelta
Deal found 5/27$360
Tue 10/86:50 amSJC - MDW
1 stop9h 09mDelta
Tue 10/152:00 pmMDW - SJC
1 stop8h 39mDelta
Deal found 5/28$369
Cheap Frontier flights from San Jose to Midway
Explore cheap flight options specifically provided by Frontier for the route between San Jose and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
To aid your search, here are some of the cheapest Frontier flights we've found from San Jose to Chicago. Deals frequently update to provide users with more options.
Wed 9/410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sat 9/711:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$180
Sat 8/1710:20 pmSJC - MDW
1 stop6h 13mFrontier
Sat 8/2410:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 5/27$183
Wed 8/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sat 8/1711:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$188
Wed 9/410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 9/811:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$196
Wed 8/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Mon 8/196:00 amMDW - SJC
1 stop12h 57mFrontier
Deal found 5/27$200
Wed 8/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 8/1811:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/28$202
Wed 8/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 8/1811:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$204
Mon 8/1211:30 amSJC - MDW
1 stop22h 22mFrontier
Tue 8/1310:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 5/28$208
Thu 9/510:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 9/811:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$212
Cheap San Jose to Midway flights in May & June 2024
Find cheap flight options from San Jose to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,696,634 searches. Prices were last updated on May 28, 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.
Mon 6/246:50 pmSJC - MDW
Nonstop4h 05mSouthwest
Wed 6/268:45 amMDW - SJC
Nonstop4h 30mSouthwest
Deal found 5/28$475
Mon 6/245:00 pmSJC - MDW
1 stop5h 55mSouthwest
Wed 6/268:45 amMDW - SJC
Nonstop4h 30mSouthwest
Deal found 5/28$479
Tue 6/256:30 amSJC - MDW
1 stop9h 29mDelta
Tue 7/29:29 amMDW - SJC
2 stops8h 50mDelta
Deal found 5/27$595
Sat 6/155:00 pmSJC - MDW
2 stops13h 48mDelta
Tue 6/183:45 pmMDW - SJC
1 stop8h 57mDelta
Deal found 5/28$610
Sat 6/155:00 pmSJC - MDW
2 stops13h 48mDelta
Tue 6/181:24 pmMDW - SJC
2 stops10h 46mDelta
Deal found 5/28$635
Fri 6/77:00 pmSJC - MDW
2 stops11h 48mDelta
Sat 6/2912:07 pmMDW - SJC
1 stop7h 28mDelta
Deal found 5/28$637
Fri 6/710:15 pmSJC - MDW
1 stop9h 36mDelta
Sat 6/2912:07 pmMDW - SJC
1 stop7h 28mDelta
Deal found 5/28$654
Wed 6/2612:26 pmSJC - MDW
1 stop7h 20mDelta
Wed 7/39:34 amMDW - SJC
2 stops8h 45mDelta
Deal found 5/27$689
Tue 6/256:15 amSJC - MDW
2 stops8h 49mDelta
Tue 7/29:29 amMDW - SJC
2 stops8h 50mDelta
Deal found 5/27$694
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 2,696,634 searches. Data last updated May 28, 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.
Wed 9/410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sat 9/711:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$180
Sat 8/1710:20 pmSJC - MDW
1 stop6h 13mFrontier
Sat 8/2410:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 5/27$183
Wed 8/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sat 8/1711:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$188
Wed 9/410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 9/811:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$196
Wed 8/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Mon 8/196:00 amMDW - SJC
1 stop12h 57mFrontier
Deal found 5/27$200
Wed 8/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 8/1811:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/28$202
Wed 8/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 8/1811:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$204
Mon 8/1211:30 amSJC - MDW
1 stop22h 22mFrontier
Tue 8/1310:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 5/28$208
Thu 9/510:20 pmSJC - MDW
1 stop6h 13mFrontier
Sun 9/811:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 5/27$212
Non-stop flights to Midway from San Jose
Discover non-stop flight options from San Jose to Midway. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
For a quicker trip, book one of these direct flights from San Jose to Chicago. Those looking to potentially save on 1 or 2-stop flights from San Jose to Chicago should utilize the search form at the the top of the page.
Mon 6/246:50 pmSJC - MDW
Nonstop4h 05mSouthwest
Wed 6/268:45 amMDW - SJC
Nonstop4h 30mSouthwest
Deal found 5/28$475
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 2,696,634 searches. Data last updated May 28, 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.
Fri 6/77:00 pmSJC - MDW
2 stops11h 48mDelta
Sat 6/2912:07 pmMDW - SJC
1 stop7h 28mDelta
Deal found 5/28$637
Fri 6/710:15 pmSJC - MDW
1 stop9h 36mDelta
Sat 6/2912:07 pmMDW - SJC
1 stop7h 28mDelta
Deal found 5/28$654
Fri 6/77:00 pmSJC - MDW
2 stops11h 48mDelta
Sat 6/299:28 amMDW - SJC
2 stops10h 07mDelta
Deal found 5/28$740
Mon 6/36:37 amSJC - MDW
1 stop9h 21mDelta
Wed 6/52:15 pmMDW - SJC
1 stop8h 18mDelta
Deal found 5/27$802
Fri 6/710:15 pmSJC - MDW
1 stop9h 36mDelta
Sat 6/2912:07 pmMDW - SJC
1 stop7h 28mDelta
Deal found 5/27$804
Fri 6/77:00 pmSJC - MDW
2 stops11h 48mDelta
Sun 6/92:24 pmMDW - SJC
1 stop8h 13mDelta
Deal found 5/28$807
Mon 6/310:20 pmSJC - MDW
2 stops13h 15mDelta
Wed 6/58:45 amMDW - SJC
2 stops12h 28mDelta
Deal found 5/27$812
Fri 6/710:15 pmSJC - MDW
1 stop9h 36mDelta
Sun 6/92:24 pmMDW - SJC
1 stop8h 13mDelta
Deal found 5/28$824
Fri 6/77:00 pmSJC - MDW
2 stops11h 48mDelta
Mon 6/103:45 pmMDW - SJC
1 stop8h 57mDelta
Deal found 5/27$829
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 2,696,634 searches. Data last updated May 28, 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.
Tue 9/310:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 5/27$95
Fri 8/1610:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 5/27$108
Tue 7/2311:30 amSJC - MDW
1 stop7h 20mFrontier
Deal found 5/27$110
Thu 9/510:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 5/27$111
Thu 8/812:51 pmSJC - MDW
1 stop7h 09mFrontier
Deal found 5/27$118
Tue 10/810:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 5/27$129
Thu 6/277:00 amSJC - MDW
1 stop20h 14mMultiple Airlines
Deal found 5/27$153
Sat 10/1912:05 pmSJC - MDW
1 stop7h 39mDelta
Deal found 5/27$174
Fri 8/167:00 pmSJC - MDW
2 stops11h 38mDelta
Deal found 5/27$179
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 2,696,634 searches. Data last updated May 28, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$180 - $475
Route
Depart
Return
Price
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Wed 9/4
1 stop6h 13m
Chicago Midway
Sat 9/7
1 stop8h 34m
$180
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Sat 8/17
1 stop6h 13m
Chicago Midway
Sat 8/24
1 stop20h 51m
$183
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Wed 8/14
1 stop6h 13m
Chicago Midway
Sat 8/17
1 stop8h 34m
$188
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Wed 9/4
1 stop6h 13m
Chicago Midway
Sun 9/8
1 stop8h 34m
$196
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Wed 8/14
1 stop6h 13m
Chicago Midway
Mon 8/19
1 stop12h 57m
$200
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Wed 8/14
1 stop6h 13m
Chicago Midway
Sun 8/18
1 stop8h 34m
$202
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Wed 8/14
1 stop6h 13m
Chicago Midway
Sun 8/18
1 stop8h 34m
$204
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Sat 9/14
1 stop7h 39m
Chicago Midway
Wed 9/18
1 stop8h 39m
$328
San JoseChicago Midway
SJC - MDW
SJCMDW
San Jose
Mon 6/24
Nonstop4h 05m
Chicago Midway
Wed 6/26
Nonstop4h 30m
$475
When is the cheapest time 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 May 26, 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. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 |
|---|
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 May 28, 2024.
Peruse reviews from past customers who have flown with Delta, Frontier and Southwest 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.
Southwest
5,984 reviews
Food
7.3
Overall
8.2
Entertainment
7.8
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 10
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Southwest
5,984 reviews
Southwest
5,984 reviews
Food
7.3
Overall
8.2
Entertainment
7.8
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 10
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
10,476 reviews
Southwest
5,984 reviews
Food
7.3
Overall
8.2
Entertainment
7.8
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 10
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
1,480 reviews
Southwest
5,984 reviews
Food
7.3
Overall
8.2
Entertainment
7.8
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 10
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
4,016 reviews
Southwest
5,984 reviews
Food
7.3
Overall
8.2
Entertainment
7.8
Comfort
8.1
Crew
8.7
Boarding
8.3
Reviews
1 / 10
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
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.
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Alternative routes for San Jose to MidwaySee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
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 2,696,634 searches. Data last updated May 28, 2024.
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.
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 May 28, 2024.
| 29%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 71%of flight departures | Morning6 am to noon |
| 0%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 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 May 28, 2024.
| Sunday | 2daily flights |
|---|---|
| Monday | 7daily flights |
| Tuesday | 6daily flights |
| Wednesday | 6daily flights |
| Thursday | 7daily flights |
| Friday | 7daily flights |
| Saturday | 2daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Fly with Cheapflights
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from San Jose to Midway?
When you search for this flight from San Jose to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
Why should you use Cheapflights to find cheap flight tickets from San Jose to Midway?
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from San Jose to Midway for you. Better yet — we are completely free to use.
Can Cheapflights find flights from San Jose to Midway with no change fees?
Certainly. Search results for flights to Midway from San Jose shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from San Jose to Midway become cheaper?
Not ready to book yet? You can track prices for flights from San Jose to Midway on Cheapflights with our Price Alert feature and get notified when better prices are available.