$139+ Cheap flights from Midway (MDW) to San José (SJO)
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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Apr 4 — Apr 111
Round-trip
1 adult, Economy
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Find cheap flights from Midway to San José with Cheapflights
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Cheapest flights from Midway to San JoséExplore the most affordable flight options available from Midway to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 5, 2026.
Explore the most affordable flight options available from Midway to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 4/136:30 am
MDW
- SJO
1 stop9h 35m
Multiple Airlines
Tue 4/217:48 pm
SJO
- MDW
2 stops16h 12m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 3/3. 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 4/1312:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Wed 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/3![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 3/2. 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 4/3010:15 am
MDW
- SJO
1 stop9h 45m
Southwest
Tue 5/51:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/2![Southwest logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/309:51 pm
MDW
- SJO
1 stop13h 51m
Multiple Airlines
Mon 4/611:38 am
SJO
- MDW
2 stops33h 41m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 3/4. 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.
Sat 4/116:30 am
MDW
- SJO
1 stop9h 35m
Multiple Airlines
Tue 4/147:48 pm
SJO
- MDW
2 stops16h 12m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 3/5. 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 5/56:00 am
MDW
- SJO
1 stop7h 10m
Southwest
Mon 5/111:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 3/5![Southwest logo]()
$413
This Southwest deal was found by Cheapflights users on 3/1. 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 4/1312:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Tue 4/211:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/1![Southwest logo]()
$421
This Southwest deal was found by Cheapflights users on 3/3. 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 4/812:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Wed 4/159:00 am
SJO
- MDW
2 stops10h 00m
Southwest
Deal found 3/3![Southwest logo]()
$434
This Southwest deal was found by Cheapflights users on 3/2. 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 4/2112:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Fri 5/19:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Deal found 3/2![Southwest logo]()
$436
This Southwest deal was found by Cheapflights users on 3/1. 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 4/2912:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Mon 5/41:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 3/1![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 3/2. 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 5/612:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Wed 5/139:00 am
SJO
- MDW
1 stop7h 30m
Southwest
Deal found 3/2![Southwest logo]()
$439
Best flights from Midway to San JoséDiscover carefully curated flight deals from Midway to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 5, 2026.
Discover carefully curated flight deals from Midway to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 5, 2026.
This Southwest deal was found by Cheapflights users on 3/2. 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 4/2112:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Fri 5/19:00 am
SJO
- MDW
2 stops12h 45m
Southwest
Deal found 3/2![Southwest logo]()
$440
This Delta deal was found by Cheapflights users on 3/2. 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 3/1112:47 pm
MDW
- SJO
1 stop9h 28m
Delta
Sat 3/147:00 am
SJO
- MDW
2 stops9h 54m
Delta
Deal found 3/2![Delta logo]()
$619
This Southwest deal was found by Cheapflights users on 3/5. 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 5/95:00 am
MDW
- SJO
1 stop8h 15m
Southwest
Sat 5/169:00 am
SJO
- MDW
1 stop12h 35m
Southwest
Deal found 3/5![Southwest logo]()
$464
This Southwest deal was found by Cheapflights users on 3/2. 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 5/17:50 am
MDW
- SJO
2 stops12h 10m
Southwest
Wed 5/139:00 am
SJO
- MDW
2 stops11h 50m
Southwest
Deal found 3/2![Southwest logo]()
$553
This Southwest deal was found by Cheapflights users on 3/3. 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 3/316:00 am
MDW
- SJO
1 stop7h 55m
Southwest
Tue 4/71:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/3![Southwest logo]()
$557
This Southwest deal was found by Cheapflights users on 3/1. 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 5/106:50 am
MDW
- SJO
1 stop7h 10m
Southwest
Sun 5/179:00 am
SJO
- MDW
1 stop9h 10m
Southwest
Deal found 3/1![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 3/1. 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.
Sat 3/2110:45 am
MDW
- SJO
1 stop11h 30m
Delta
Mon 3/301:20 pm
SJO
- MDW
1 stop8h 11m
Delta
Deal found 3/1![Delta logo]()
$949
This Southwest deal was found by Cheapflights users on 3/1. 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 3/167:25 am
MDW
- SJO
2 stops13h 15m
Southwest
Thu 4/301:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 3/1![Southwest logo]()
$649
This Southwest deal was found by Cheapflights users on 3/1. 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 5/3111:25 am
MDW
- SJO
1 stop8h 35m
Southwest
Mon 6/88:45 am
SJO
- MDW
1 stop10h 25m
Southwest
Deal found 3/1![Southwest logo]()
$671
This Southwest deal was found by Cheapflights users on 3/3. 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 3/178:10 am
MDW
- SJO
2 stops12h 30m
Southwest
Fri 3/201:55 pm
SJO
- MDW
1 stop7h 55m
Southwest
Deal found 3/3![Southwest logo]()
$946
This Southwest deal was found by Cheapflights users on 3/1. 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 3/156:05 am
MDW
- SJO
1 stop7h 50m
Southwest
Fri 3/201:55 pm
SJO
- MDW
1 stop7h 55m
Southwest
Deal found 3/1![Southwest logo]()
$956
This Southwest deal was found by Cheapflights users on 3/3. 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 3/138:15 am
MDW
- SJO
1 stop12h 25m
Southwest
Thu 3/198:45 am
SJO
- MDW
1 stop10h 30m
Southwest
Deal found 3/3![Southwest logo]()
$992
Last-minute flights from Midway to San JoséDiscover last-minute flight deals from Midway to San José. Data last updated March 5, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San José. Data last updated March 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/309:51 pm
MDW
- SJO
1 stop13h 51m
Multiple Airlines
Mon 4/611:38 am
SJO
- MDW
2 stops33h 41m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 3/309:42 pm
MDW
- SJO
1 stop18h 23m
Multiple Airlines
Tue 4/77:45 am
SJO
- MDW
2 stops13h 34m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 3/3. 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 4/812:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Wed 4/159:00 am
SJO
- MDW
2 stops10h 00m
Southwest
Deal found 3/3![Southwest logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 3/4. 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.
Sat 4/116:30 am
MDW
- SJO
1 stop9h 35m
Multiple Airlines
Tue 4/147:48 pm
SJO
- MDW
2 stops16h 12m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 3/1. 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 4/136:30 am
MDW
- SJO
1 stop9h 35m
Multiple Airlines
Tue 4/217:48 pm
SJO
- MDW
2 stops16h 12m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 3/3. 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 4/1312:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Wed 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/3![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 3/1. 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 4/1312:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Tue 4/211:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/1![Southwest logo]()
$421
This Southwest deal was found by Cheapflights users on 3/3. 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 4/158:00 am
MDW
- SJO
2 stops12h 00m
Southwest
Wed 4/221:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/3![Southwest logo]()
$440
This Southwest deal was found by Cheapflights users on 3/2. 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 4/2112:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Fri 5/19:00 am
SJO
- MDW
1 stop9h 00m
Southwest
Deal found 3/2![Southwest logo]()
$436
This Southwest deal was found by Cheapflights users on 3/1. 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 4/2912:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Mon 5/41:10 pm
SJO
- MDW
1 stop7h 45m
Southwest
Deal found 3/1![Southwest logo]()
$437
This Southwest deal was found by Cheapflights users on 3/2. 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 4/3010:15 am
MDW
- SJO
1 stop9h 45m
Southwest
Tue 5/51:10 pm
SJO
- MDW
1 stop8h 55m
Southwest
Deal found 3/2![Southwest logo]()
$403
One-way flights from Midway to San JoséSearch for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated March 5, 2026.
Search for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Data last updated March 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Tue 4/217:30 am
MDW
- SJO
2 stops28h 08m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$139
This Priceline deal was found by Cheapflights users on 3/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:41 pm
MDW
- SJO
1 stop14h 04m
Frontier
Deal found 3/2![Frontier logo]()
$154
This Southwest deal was found by Cheapflights users on 3/5. 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 4/2112:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 3/5![Southwest logo]()
$159
This Trip.com deal was found by Cheapflights users on 3/5. 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.
Mon 3/96:00 am
MDW
- SJO
1 stop10h 17m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Wed 4/152:15 pm
MDW
- SJO
2 stops22h 18m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 3/3. 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 4/1512:15 pm
MDW
- SJO
1 stop7h 45m
Southwest
Deal found 3/3![Southwest logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 3/2. 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.
Sun 5/176:00 am
MDW
- SJO
2 stops30h 33m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Thu 4/166:00 am
MDW
- SJO
2 stops30h 33m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/179:14 am
MDW
- SJO
2 stops10h 36m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 3/162:41 pm
MDW
- SJO
2 stops21h 33m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 3/3. 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 4/1612:10 pm
MDW
- SJO
1 stop7h 50m
Southwest
Deal found 3/3![Southwest logo]()
$210
Find flight deals from Midway to San José
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José (SJO). 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 March 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $391 (Kiwi.com) |
One-way from | $139 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $596 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San José 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 March 5, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 4/21
12:15 pm-7:00 pm
1 stop7h 45m
San José Juan Santamaria Intl
Fri 5/1
9:00 am-10:45 pm
2 stops12h 45m
$440
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 5/9
5:00 am-12:15 pm
1 stop8h 15m
San José Juan Santamaria Intl
Sat 5/16
9:00 am-10:35 pm
1 stop12h 35m
$464
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 5/1
7:50 am-7:00 pm
2 stops12h 10m
San José Juan Santamaria Intl
Wed 5/13
9:00 am-9:50 pm
2 stops11h 50m
$553
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/31
6:00 am-12:55 pm
1 stop7h 55m
San José Juan Santamaria Intl
Tue 4/7
1:10 pm-11:05 pm
1 stop8h 55m
$557
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 5/10
6:50 am-1:00 pm
1 stop7h 10m
San José Juan Santamaria Intl
Sun 5/17
9:00 am-7:10 pm
1 stop9h 10m
$590
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 3/11
12:47 pm-9:15 pm
1 stop9h 28m
San José Juan Santamaria Intl
Sat 3/14
7:00 am-5:54 pm
2 stops9h 54m
$619
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 3/16
7:25 am-7:40 pm
2 stops13h 15m
San José Juan Santamaria Intl
Thu 4/30
1:10 pm-9:55 pm
1 stop7h 45m
$649
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 5/31
11:25 am-7:00 pm
1 stop8h 35m
San José Juan Santamaria Intl
Mon 6/8
8:45 am-8:10 pm
1 stop10h 25m
$671
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Tue 3/17
8:10 am-7:40 pm
2 stops12h 30m
San José Juan Santamaria Intl
Fri 3/20
1:55 pm-10:50 pm
1 stop7h 55m
$946
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 3/21
10:45 am-9:15 pm
1 stop11h 30m
San José Juan Santamaria Intl
Mon 3/30
1:20 pm-10:31 pm
1 stop8h 11m
$949
Showing 1-10 of 24 resultsSorted by cheapest first
Compare providers for flights from Midway to San José
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 Midway to San José in March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San José flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San José flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San José 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 Chicago Midway Airport-San José 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 Midway to San José
Have a flexible travel schedule? Discover the best time to fly to San José from Midway with our price prediction graph.
MDW-SJO
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 Chicago Midway Airport to San José
How often are flights from Chicago to San José delayed?
About 100% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 97 minutes.
What is the most punctual flight time for Chicago to San José flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
Reviews of airlines servicing San José
Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated March 5, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San José, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Midway to San José. 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 José?
Book flights to San José if you plan to visit one of these locationsAlajuela
Monteverde
Jacó
Heredia
Dominical
Manuel Antonio
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Midway and San José flights
Browse other Midway and San José flight options. Last updated on March 5, 2026.
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Top airline flying from Midway to San José
Discover the top airline that operate flights from Midway to San José. 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 March 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$572 | FlexibilityNo cancel fee | On-time63% |