$183+ Cheap flights from San José (SJO) 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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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
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Cheapest flights from San José to MidwayExplore the most affordable flight options available from San José to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 2026.
Explore the most affordable flight options available from San José to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/6. 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.
Tue 9/11:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Tue 9/156:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 6/6![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 9/11:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Mon 9/77:55 am
MDW
- SJO
2 stops11h 45m
Southwest
Deal found 6/10![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 9/151:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Sat 9/1910:25 am
MDW
- SJO
1 stop8h 35m
Southwest
Deal found 6/8![Southwest logo]()
$404
This Southwest deal was found by Cheapflights users on 6/9. 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.
Sun 8/309:00 am
SJO
- MDW
2 stops9h 30m
Southwest
Sat 9/510:10 am
MDW
- SJO
2 stops8h 50m
Southwest
Deal found 6/9![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 6/7. 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.
Tue 9/151:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Sun 9/207:10 am
MDW
- SJO
2 stops12h 30m
Southwest
Deal found 6/7![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 6/8. 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.
Sun 9/209:00 am
SJO
- MDW
1 stop11h 20m
Southwest
Mon 9/287:15 am
MDW
- SJO
1 stop6h 30m
Southwest
Deal found 6/8![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 9/249:00 am
SJO
- MDW
2 stops11h 00m
Southwest
Mon 9/285:00 am
MDW
- SJO
1 stop8h 45m
Southwest
Deal found 6/8![Southwest logo]()
$426
This Delta deal was found by Cheapflights users on 6/9. 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.
Mon 9/211:25 pm
SJO
- MDW
1 stop8h 00m
Delta
Mon 9/286:05 am
MDW
- SJO
1 stop6h 49m
Delta
Deal found 6/9![Delta logo]()
$428
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 10/71:00 pm
SJO
- MDW
1 stop9h 00m
Southwest
Tue 10/136:05 am
MDW
- SJO
1 stop7h 00m
Southwest
Deal found 6/8![Southwest logo]()
$430
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 9/11:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Sun 9/67:45 am
MDW
- SJO
2 stops11h 55m
Southwest
Deal found 6/10![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 6/6. 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.
Tue 9/151:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Mon 9/2110:05 am
MDW
- SJO
1 stop9h 35m
Southwest
Deal found 6/6![Southwest logo]()
$438
This Southwest deal was found by Cheapflights users on 6/7. 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.
Fri 10/91:30 pm
SJO
- MDW
2 stops10h 15m
Southwest
Tue 10/136:05 am
MDW
- SJO
1 stop7h 00m
Southwest
Deal found 6/7![Southwest logo]()
$442
Best flights from San José to MidwayDiscover carefully curated flight deals from San José to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 10, 2026.
Discover carefully curated flight deals from San José to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 8/111:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Tue 8/1810:10 am
MDW
- SJO
2 stops9h 30m
Southwest
Deal found 6/8![Southwest logo]()
$573
This Delta deal was found by Cheapflights users on 6/7. 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.
Tue 8/251:14 pm
SJO
- MDW
1 stop8h 22m
Delta
Mon 8/316:05 am
MDW
- SJO
1 stop6h 44m
Delta
Deal found 6/7![Delta logo]()
$653
This Southwest deal was found by Cheapflights users on 6/9. 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.
Sat 6/132:35 pm
SJO
- MDW
1 stop7h 35m
Southwest
Sat 6/2710:15 am
MDW
- SJO
2 stops10h 25m
Southwest
Deal found 6/9![Southwest logo]()
$589
This Southwest deal was found by Cheapflights users on 6/8. 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.
Fri 8/219:00 am
SJO
- MDW
2 stops11h 55m
Southwest
Tue 8/2511:10 am
MDW
- SJO
2 stops8h 30m
Southwest
Deal found 6/8![Southwest logo]()
$635
This Southwest deal was found by Cheapflights users on 6/9. 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.
Sat 6/132:35 pm
SJO
- MDW
1 stop7h 35m
Southwest
Fri 6/197:50 am
MDW
- SJO
2 stops12h 50m
Southwest
Deal found 6/9![Southwest logo]()
$710
This Southwest deal was found by Cheapflights users on 6/10. 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.
Thu 7/91:40 pm
SJO
- MDW
1 stop8h 25m
Southwest
Tue 7/2110:15 am
MDW
- SJO
2 stops10h 25m
Southwest
Deal found 6/10![Southwest logo]()
$750
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 6/241:40 pm
SJO
- MDW
1 stop9h 10m
Southwest
Thu 7/28:55 am
MDW
- SJO
2 stops11h 45m
Southwest
Deal found 6/10![Southwest logo]()
$754
This Southwest deal was found by Cheapflights users on 6/7. 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.
Thu 7/98:45 am
SJO
- MDW
1 stop8h 15m
Southwest
Sun 7/127:25 am
MDW
- SJO
2 stops12h 15m
Southwest
Deal found 6/7![Southwest logo]()
$814
This Southwest deal was found by Cheapflights users on 6/7. 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.
Wed 7/81:40 pm
SJO
- MDW
1 stop9h 15m
Southwest
Mon 7/1311:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Deal found 6/7![Southwest logo]()
$839
Last-minute flights from San José to MidwayDiscover last-minute flight deals from San José to Midway. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Midway. Data last updated June 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/7. 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.
Thu 6/118:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Wed 6/171:10 pm
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 6/7![Southwest logo]()
$581
This Southwest deal was found by Cheapflights users on 6/7. 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.
Thu 7/238:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Thu 7/3010:10 am
MDW
- SJO
1 stop10h 30m
Southwest
Deal found 6/7![Southwest logo]()
$548
This Southwest deal was found by Cheapflights users on 6/8. 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.
Sat 7/258:45 am
SJO
- MDW
1 stop14h 00m
Southwest
Tue 7/2810:15 am
MDW
- SJO
2 stops10h 25m
Southwest
Deal found 6/8![Southwest logo]()
$539
This Southwest deal was found by Cheapflights users on 6/6. 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.
Sun 7/268:45 am
SJO
- MDW
2 stops12h 00m
Southwest
Wed 8/2611:10 am
MDW
- SJO
2 stops8h 30m
Southwest
Deal found 6/6![Southwest logo]()
$545
This Southwest deal was found by Cheapflights users on 6/9. 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.
Sun 7/268:45 am
SJO
- MDW
2 stops12h 00m
Southwest
Thu 7/3011:50 am
MDW
- SJO
1 stop8h 50m
Southwest
Deal found 6/9![Southwest logo]()
$582
This Southwest deal was found by Cheapflights users on 6/7. 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.
Wed 7/298:45 am
SJO
- MDW
2 stops10h 05m
Southwest
Thu 8/67:15 am
MDW
- SJO
1 stop6h 30m
Southwest
Deal found 6/7![Southwest logo]()
$541
This Southwest deal was found by Cheapflights users on 6/7. 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.
Wed 7/298:45 am
SJO
- MDW
2 stops10h 05m
Southwest
Sun 8/98:50 am
MDW
- SJO
2 stops10h 50m
Southwest
Deal found 6/7![Southwest logo]()
$585
One-way flights from San José to MidwaySearch for one-way flight options from San José to Midway. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
Search for one-way flight options from San José to Midway. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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.
Thu 9/39:00 am
SJO
- MDW
1 stop8h 00m
Southwest
Deal found 6/9![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 6/7. 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.
Thu 10/81:30 pm
SJO
- MDW
1 stop9h 40m
Southwest
Deal found 6/7![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 6/8. 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.
Sat 7/258:45 am
SJO
- MDW
1 stop14h 00m
Southwest
Deal found 6/8![Southwest logo]()
$281
This Delta deal was found by Cheapflights users on 6/10. 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.
Fri 10/91:23 pm
SJO
- MDW
1 stop7h 47m
Delta
Deal found 6/10![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 7/98:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Deal found 6/8![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 8/269:00 am
SJO
- MDW
2 stops11h 50m
Southwest
Deal found 6/8![Southwest logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:20 am
SJO
- MDW
2 stops34h 47m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/72:15 am
SJO
- MDW
3 stops18h 56m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$341
Find flight deals from San José to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) 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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $390 (Southwest) |
One-way from | $183 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $506 |
Cheapflights Fare Finder
Customize your flight search to find flights from San José 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 June 10, 2026.
Use the filters below to find and compare flights from San José to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 8/11
1:40 pm-11:10 pm
1 stop8h 30m
Chicago Midway
Tue 8/18
10:10 am-6:40 pm
2 stops9h 30m
$573
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 6/13
2:35 pm-11:10 pm
1 stop7h 35m
Chicago Midway
Sat 6/27
10:15 am-7:40 pm
2 stops10h 25m
$589
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fri 8/21
9:00 am-9:55 pm
2 stops11h 55m
Chicago Midway
Tue 8/25
11:10 am-6:40 pm
2 stops8h 30m
$635
Quickest round-trip
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 8/25
1:14 pm-10:36 pm
1 stop8h 22m
Chicago Midway
Mon 8/31
6:05 am-11:49 am
1 stop6h 44m
$653
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sat 6/13
2:35 pm-11:10 pm
1 stop7h 35m
Chicago Midway
Fri 6/19
7:50 am-7:40 pm
2 stops12h 50m
$710
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 7/9
1:40 pm-11:05 pm
1 stop8h 25m
Chicago Midway
Tue 7/21
10:15 am-7:40 pm
2 stops10h 25m
$750
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 6/24
1:40 pm-11:50 pm
1 stop9h 10m
Chicago Midway
Thu 7/2
8:55 am-7:40 pm
2 stops11h 45m
$754
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 7/9
8:45 am-6:00 pm
1 stop8h 15m
Chicago Midway
Sun 7/12
7:25 am-6:40 pm
2 stops12h 15m
$814
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 7/8
1:40 pm-11:55 pm
1 stop9h 15m
Chicago Midway
Mon 7/13
11:50 am-7:40 pm
1 stop8h 50m
$839
Cheapest one-way
Quickest one-way
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 9/3
9:00 am-6:00 pm
1 stop8h 00m
$183
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from San José 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 José to Midway in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San José-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 José-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San José-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 José-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 José to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San José with our price prediction graph.
SJO-MDW
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.
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 10, 2026.
Read through reviews of airlines operating flights from San José to Chicago Midway Airport, such as Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from San José 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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.
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Alternative routes for San José to Midway
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Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from San José to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 10, 2026.
San José and Midway flights
Browse other San José and Midway flight options. Last updated on June 10, 2026.
Other flights from San José
Browse through other flights departing from San José. Flights are based on user searches made on Cheapflights and were last updated on June 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from San José to Midway
Discover the top airline that operate flights from San José 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 June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$463 | Average$507 | FlexibilityNo cancel fee | On-time63% |