$63+ Cheap flights from San Jose (SJC) to Midway (MDW)
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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MDW
Feb 25 — Mar 41
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from San Jose to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 February 20, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $194 (Trip.com) |
One-way from | $63 (Trip.com) |
Popular in | June |
Cheapest in | March |
Average price | $403 |
Good round-trip deal | $430 or less |
Good one-way deal | $214 or less |
Find flight deals from San Jose to Midway
Cheapest flights from San Jose to MidwayExplore the most affordable flight options available from San Jose to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.
Explore the most affordable flight options available from San Jose to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.
This Trip.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/24:03 pmSJC - MDW
1 stop6h 18mFrontier
Mon 4/76:45 amMDW - SJC
2 stops14h 37mFrontier
Deal found 2/18![Frontier logo]()
$194
This Trip.com deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/45:40 pmSJC - MDW
2 stops19h 26mMultiple Airlines
Fri 3/76:40 amMDW - SJC
1 stop10h 23mMultiple Airlines
Deal found 2/20![Multiple Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/166:15 amSJC - MDW
1 stop9h 04mDelta
Tue 4/2210:20 amMDW - SJC
2 stops13h 49mDelta
Deal found 2/20![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/75:40 pmSJC - MDW
1 stop6h 10mSouthwest
Thu 4/106:25 pmMDW - SJC
Nonstop4h 35mSouthwest
Deal found 2/19![Southwest logo]()
$361
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 2,558,603 searches. Data last updated February 20, 2025.
Fly from
San Jose
Fly to
Midway
Route
Depart
Return
Price
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 4/2
4:03 pm-12:21 am
1 stop6h 18m
Chicago Midway
Mon 4/7
6:45 am-7:22 pm
2 stops14h 37m
$194
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 3/4
5:40 pm-3:06 pm
2 stops19h 26m
Chicago Midway
Fri 3/7
6:40 am-3:03 pm
1 stop10h 23m
$279
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Wed 4/16
6:15 am-5:19 pm
1 stop9h 04m
Chicago Midway
Tue 4/22
10:20 am-10:09 pm
2 stops13h 49m
$298
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Mon 4/7
5:40 pm-1:50 am
1 stop6h 10m
Chicago Midway
Thu 4/10
6:25 pm-9:00 pm
Nonstop4h 35m
$361
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 4/15
7:28 pm-5:23 am
1 stop7h 55m
$63
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 4/1
6:25 pm-8:45 am
2 stops12h 20m
$137
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Tue 4/8
6:40 am-12:50 pm
Nonstop4h 10m
$176
San JoseChicago
SJC - MDW
SJCMDW
San Jose
Thu 5/8
6:00 am-10:09 am
3 stops26h 09m
$219
Compare providers for flights from San Jose to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Jose to Midway in February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Jose-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Jose-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Jose-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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.
Travel insights for flights from San Jose to Midway
Get recent, data-driven insights about flights from San Jose to Midway including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from San Jose to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from San Jose to Chicago Midway Airport (average of $160). Flying from San Jose to Chicago Midway Airport in November 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.
What is the cheapest time of day to fly from SJC to MDW?
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 February 20, 2025.
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 34% on your trip compared to booking a flight at noon.
Rainfall in Midway by month
Plan your trip to Midway by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.
Temperature in Midway by month
Plan your trip to Midway by taking into account the average temperature totals by month.
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 February 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier 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.
Food
7.1
Boarding
8.2
Overall
8.1
Entertainment
7.6
Comfort
8.1
Crew
8.7
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
Food
7.1
Boarding
8.2
Overall
8.1
Entertainment
7.6
Comfort
8.1
Crew
8.7
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
Food
7.1
Boarding
8.2
Overall
8.1
Entertainment
7.6
Comfort
8.1
Crew
8.7
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
Food
7.1
Boarding
8.2
Overall
8.1
Entertainment
7.6
Comfort
8.1
Crew
8.7
Reviews
1 / 20
10.0
ExcellentArlene,May 2024
SAN - OAK
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.
Traveling to a place near San Jose?
Book flights to San Jose if you plan to visit one of these locationsMerrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for San Jose to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from San Jose to Midway
Discover the top 4 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 2,558,603 searches. Data last updated February 20, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$207 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$203 | Average$517 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$241 | Average$650 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$367 | Average$487 | FlexibilityNo cancel fee | On-time63% |