$208+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Mai 28 — Jun 41
Round-trip
1 adult, Economy
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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 April 28, 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 April 28, 2026.
This Delta deal was found by Cheapflights users on 4/25. 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.
Mi 10/211:23 pm
SJO
- MDW
2 stops18h 22m
Delta
Di 10/276:00 am
MDW
- SJO
1 stop6h 58m
Delta
Deal found 4/25![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 4/27. 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.
Do 12/247:00 am
SJO
- MDW
1 stop14h 45m
Delta
Do 12/319:30 am
MDW
- SJO
2 stops12h 45m
Delta
Deal found 4/27![Delta logo]()
$432
This Delta deal was found by Cheapflights users on 4/26. 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.
So 12/207:00 am
SJO
- MDW
1 stop14h 45m
Delta
Do 12/319:30 am
MDW
- SJO
2 stops12h 45m
Delta
Deal found 4/26![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 4/28. 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.
Mi 10/71:23 pm
SJO
- MDW
1 stop7h 22m
Delta
Mi 10/146:00 am
MDW
- SJO
1 stop6h 58m
Delta
Deal found 4/28![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 4/28. 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.
Sa 11/147:00 am
SJO
- MDW
1 stop9h 25m
Delta
Sa 11/281:05 pm
MDW
- SJO
1 stop9h 10m
Delta
Deal found 4/28![Delta logo]()
$455
This Southwest deal was found by Cheapflights users on 4/23. 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.
Mi 8/191:40 pm
SJO
- MDW
1 stop8h 30m
Southwest
Mi 9/166:15 am
MDW
- SJO
1 stop7h 30m
Southwest
Deal found 4/23![Southwest logo]()
$468
This Delta deal was found by Cheapflights users on 4/28. 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.
Do 10/81:23 pm
SJO
- MDW
1 stop7h 22m
Delta
Mi 10/146:00 am
MDW
- SJO
1 stop6h 58m
Delta
Deal found 4/28![Delta logo]()
$476
This Southwest deal was found by Cheapflights users on 4/25. 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.
Fr 9/189:00 am
SJO
- MDW
1 stop11h 30m
Southwest
Di 9/2210:10 am
MDW
- SJO
2 stops9h 30m
Southwest
Deal found 4/25![Southwest logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Mo 5/187:00 am
SJO
- MDW
1 stop7h 57m
Multiple Airlines
So 5/2412:27 pm
MDW
- SJO
2 stops24h 18m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$496
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 April 28, 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 April 28, 2026.
This Southwest deal was found by Cheapflights users on 4/26. 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.
Fr 5/11:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Mi 5/612:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 4/26![Southwest logo]()
$555
This Delta deal was found by Cheapflights users on 4/24. 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.
Di 7/211:16 pm
SJO
- MDW
1 stop7h 59m
Delta
Do 7/306:05 am
MDW
- SJO
1 stop6h 46m
Delta
Deal found 4/24![Delta logo]()
$562
This Southwest deal was found by Cheapflights users on 4/23. 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.
Fr 5/89:00 am
SJO
- MDW
1 stop9h 00m
Southwest
So 5/1011:25 am
MDW
- SJO
1 stop8h 35m
Southwest
Deal found 4/23![Southwest logo]()
$555
This Delta deal was found by Cheapflights users on 4/28. 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.
Mi 7/151:16 pm
SJO
- MDW
1 stop7h 59m
Delta
Di 7/216:00 am
MDW
- SJO
1 stop6h 51m
Delta
Deal found 4/28![Delta logo]()
$621
This Southwest deal was found by Cheapflights users on 4/23. 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.
Mi 5/61:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Fr 5/85:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Deal found 4/23![Southwest logo]()
$588
This Southwest deal was found by Cheapflights users on 4/23. 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.
Di 5/269:00 am
SJO
- MDW
1 stop9h 45m
Southwest
Fr 5/295:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Deal found 4/23![Southwest logo]()
$625
This Southwest deal was found by Cheapflights users on 4/25. 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.
Sa 5/169:00 am
SJO
- MDW
2 stops12h 35m
Southwest
Sa 5/237:50 am
MDW
- SJO
2 stops12h 10m
Southwest
Deal found 4/25![Southwest logo]()
$630
This Southwest deal was found by Cheapflights users on 4/23. 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.
Do 5/71:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
So 5/1011:25 am
MDW
- SJO
1 stop8h 35m
Southwest
Deal found 4/23![Southwest logo]()
$633
This Southwest deal was found by Cheapflights users on 4/27. 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.
Fr 5/89:00 am
SJO
- MDW
2 stops10h 15m
Southwest
Do 5/148:55 am
MDW
- SJO
2 stops11h 05m
Southwest
Deal found 4/27![Southwest logo]()
$637
This Southwest deal was found by Cheapflights users on 4/28. 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.
Do 7/238:45 am
SJO
- MDW
2 stops9h 10m
Southwest
So 7/267:55 am
MDW
- SJO
2 stops11h 45m
Southwest
Deal found 4/28![Southwest logo]()
$669
Last-minute flights from San José to MidwayDiscover last-minute flight deals from San José to Midway. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Midway. Data last updated April 28, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/24. 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.
Mi 4/291:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Mi 5/610:05 am
MDW
- SJO
2 stops9h 55m
Southwest
Deal found 4/24![Southwest logo]()
$559
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Mi 4/297:00 am
SJO
- MDW
1 stop23h 21m
Multiple Airlines
Di 5/126:00 am
MDW
- SJO
2 stops34h 18m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$578
This Delta deal was found by Cheapflights users on 4/28. 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.
Do 4/301:21 pm
SJO
- MDW
1 stop8h 07m
Delta
Di 5/56:00 am
MDW
- SJO
1 stop6h 56m
Delta
Deal found 4/28![Delta logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Mi 5/67:00 am
SJO
- MDW
2 stops14h 02m
Multiple Airlines
Fr 5/84:52 pm
MDW
- SJO
1 stop23h 26m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$579
This Southwest deal was found by Cheapflights users on 4/23. 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.
Fr 5/89:00 am
SJO
- MDW
1 stop9h 00m
Southwest
So 5/1010:50 am
MDW
- SJO
2 stops9h 10m
Southwest
Deal found 4/23![Southwest logo]()
$555
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Mo 5/187:00 am
SJO
- MDW
1 stop7h 57m
Multiple Airlines
So 5/2412:27 pm
MDW
- SJO
2 stops24h 18m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Mo 5/187:00 am
SJO
- MDW
1 stop7h 57m
Multiple Airlines
Sa 6/611:59 am
MDW
- SJO
2 stops21h 20m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$514
This Southwest deal was found by Cheapflights users on 4/23. 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.
Mo 5/189:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Sa 6/69:55 am
MDW
- SJO
1 stop10h 45m
Southwest
Deal found 4/23![Southwest logo]()
$585
This Southwest deal was found by Cheapflights users on 4/23. 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.
Di 5/269:00 am
SJO
- MDW
2 stops11h 45m
Southwest
Fr 5/295:35 am
MDW
- SJO
1 stop7h 35m
Southwest
Deal found 4/23![Southwest logo]()
$553
This Southwest deal was found by Cheapflights users on 4/27. 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.
Mi 5/279:00 am
SJO
- MDW
2 stops12h 15m
Southwest
Sa 6/69:55 am
MDW
- SJO
1 stop10h 45m
Southwest
Deal found 4/27![Southwest logo]()
$582
This Southwest deal was found by Cheapflights users on 4/25. 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.
Mi 5/279:00 am
SJO
- MDW
1 stop7h 30m
Southwest
Mi 6/312:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 4/25![Southwest logo]()
$587
This Delta deal was found by Cheapflights users on 4/24. 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.
Do 5/281:20 pm
SJO
- MDW
2 stops18h 23m
Delta
Mi 6/31:22 pm
MDW
- SJO
2 stops23h 30m
Delta
Deal found 4/24![Delta logo]()
$562
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 April 28, 2026.
Search for one-way flight options from San José to Midway. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Mo 5/181:00 pm
SJO
- MDW
2 stops21h 09m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Do 6/111:00 pm
SJO
- MDW
2 stops25h 15m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
So 6/79:35 am
SJO
- MDW
2 stops35h 27m
Frontier
Deal found 4/27![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Do 5/289:35 am
SJO
- MDW
2 stops11h 27m
Frontier
Deal found 4/27![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
So 7/191:21 pm
SJO
- MDW
2 stops31h 47m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Mo 6/81:00 pm
SJO
- MDW
2 stops21h 12m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Fr 6/51:00 pm
SJO
- MDW
2 stops32h 02m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$248
This Delta deal was found by Cheapflights users on 4/27. 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.
Di 5/191:20 pm
SJO
- MDW
2 stops22h 22m
Delta
Deal found 4/27![Delta logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Mi 5/207:00 am
SJO
- MDW
2 stops14h 02m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
So 5/311:00 pm
SJO
- MDW
2 stops32h 02m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Di 5/261:50 am
SJO
- MDW
3 stops32h 22m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$261
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 April 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $430 (Delta) |
One-way from | $208 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $514 |
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 April 28, 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
Fr 5/1
1:10 pm-9:55 pm
1 stop7h 45m
Chicago Midway
Mi 5/6
12:15 pm-7:00 pm
1 stop7h 45m
$555
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fr 5/8
9:00 am-7:00 pm
1 stop9h 00m
Chicago Midway
So 5/10
11:25 am-7:00 pm
1 stop8h 35m
$555
Quickest round-trip
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Di 7/21
1:16 pm-10:15 pm
1 stop7h 59m
Chicago Midway
Do 7/30
6:05 am-11:51 am
1 stop6h 46m
$562
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mi 5/6
1:10 pm-11:05 pm
1 stop8h 55m
Chicago Midway
Fr 5/8
5:35 am-12:10 pm
1 stop7h 35m
$588
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mi 7/15
1:16 pm-10:15 pm
1 stop7h 59m
Chicago Midway
Di 7/21
6:00 am-11:51 am
1 stop6h 51m
$621
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Di 5/26
9:00 am-7:45 pm
1 stop9h 45m
Chicago Midway
Fr 5/29
5:35 am-12:10 pm
1 stop7h 35m
$625
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Sa 5/16
9:00 am-10:35 pm
2 stops12h 35m
Chicago Midway
Sa 5/23
7:50 am-7:00 pm
2 stops12h 10m
$630
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Do 5/7
1:10 pm-9:55 pm
1 stop7h 45m
Chicago Midway
So 5/10
11:25 am-7:00 pm
1 stop8h 35m
$633
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Fr 5/8
9:00 am-8:15 pm
2 stops10h 15m
Chicago Midway
Do 5/14
8:55 am-7:00 pm
2 stops11h 05m
$637
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Do 7/23
8:45 am-6:55 pm
2 stops9h 10m
Chicago Midway
So 7/26
7:55 am-6:40 pm
2 stops11h 45m
$669
Showing 1-10 of 18 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 April.
| 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.
Cheapflights Insights
Everything you need to know about your flight from San José to Chicago Midway Airport
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 April 28, 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.
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
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San José and Midway flights
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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 April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$463 | Average$505 | FlexibilityNo cancel fee | On-time63% |