$100+ Cheap flights from Midway (MDW) to San Juan
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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Apr 9 — Apr 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to San Juan 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 Midway to San Juan
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to San JuanExplore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 10, 2026.
Explore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 10, 2026.
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:30 am
MDW
- SJU
1 stop13h 30m
Frontier
Sat 4/183:47 pm
SJU
- MDW
1 stop7h 27m
Frontier
Deal found 3/5![Frontier logo]()
$202
This Mytrip deal was found by Cheapflights users on 3/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/9![Frontier logo]()
$208
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
- SJU
1 stop13h 49m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/9![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 3/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Fri 5/83:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/6![Frontier logo]()
$221
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/5![Frontier logo]()
$223
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:30 am
MDW
- SJU
1 stop6h 56m
Frontier
Thu 4/163:19 pm
SJU
- MDW
1 stop17h 40m
Frontier
Deal found 3/9![Frontier logo]()
$231
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 3/5![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- SJU
1 stop12h 50m
Multiple Airlines
Wed 4/156:30 am
SJU
- MDW
2 stops16h 44m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Sat 4/116:30 am
MDW
- SJU
1 stop14h 03m
Frontier
Mon 4/133:08 am
SJU
- MDW
2 stops17h 23m
Frontier
Deal found 3/7![Frontier logo]()
$241
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:01 am
MDW
- SJU
1 stop10h 28m
Frontier
Thu 4/96:07 pm
SJU
- MDW
1 stop20h 54m
Frontier
Deal found 3/5![Frontier logo]()
$242
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:14 am
MDW
- SJU
1 stop15h 47m
Frontier
Sat 5/303:01 am
SJU
- MDW
1 stop16h 35m
Frontier
Deal found 3/5![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:42 pm
MDW
- SJU
1 stop26h 37m
Frontier
Mon 4/69:10 pm
SJU
- MDW
2 stops26h 09m
Frontier
Deal found 3/6![Frontier logo]()
$246
Best flights from Midway to San JuanDiscover carefully curated flight deals from Midway to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 10, 2026.
Discover carefully curated flight deals from Midway to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 10, 2026.
This Delta deal was found by Cheapflights users on 3/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop9h 23m
Delta
Wed 4/297:30 am
SJU
- MDW
1 stop9h 56m
Delta
Deal found 3/6![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 3/6. 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.
Thu 6/411:35 am
MDW
- SJU
1 stop11h 50m
Southwest
Sun 6/75:20 am
SJU
- MDW
2 stops8h 45m
Southwest
Deal found 3/6![Southwest logo]()
$416
This Delta deal was found by Cheapflights users on 3/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:52 pm
MDW
- SJU
1 stop9h 20m
Delta
Sat 4/256:15 am
SJU
- MDW
1 stop11h 14m
Delta
Deal found 3/6![Delta logo]()
$314
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 6/612:50 pm
MDW
- SJU
2 stops8h 30m
Southwest
Mon 6/85:30 am
SJU
- MDW
2 stops9h 35m
Southwest
Deal found 3/5![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 3/9. 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 5/2812:50 pm
MDW
- SJU
2 stops10h 05m
Southwest
Mon 6/12:00 pm
SJU
- MDW
2 stops9h 20m
Southwest
Deal found 3/9![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 3/9. 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.
Fri 5/89:00 am
MDW
- SJU
2 stops10h 00m
Southwest
Mon 5/115:35 am
SJU
- MDW
2 stops8h 35m
Southwest
Deal found 3/9![Southwest logo]()
$484
This Delta deal was found by Cheapflights users on 3/9. 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.
Fri 4/1012:47 pm
MDW
- SJU
1 stop9h 28m
Delta
Tue 4/142:45 pm
SJU
- MDW
1 stop8h 43m
Delta
Deal found 3/9![Delta logo]()
$542
This Southwest deal was found by Cheapflights users on 3/8. 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 5/219:00 am
MDW
- SJU
2 stops10h 00m
Southwest
Tue 5/262:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 3/8![Southwest logo]()
$546
This Southwest deal was found by Cheapflights users on 3/8. 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.
Mon 4/138:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Mon 4/206:50 am
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 3/8![Southwest logo]()
$551
This Southwest deal was found by Cheapflights users on 3/8. 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 3/1211:35 am
MDW
- SJU
2 stops10h 20m
Southwest
Sat 3/145:30 am
SJU
- MDW
1 stop11h 40m
Southwest
Deal found 3/8![Southwest logo]()
$626
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.
Wed 4/152:35 pm
MDW
- SJU
2 stops8h 05m
Southwest
Sun 4/195:35 am
SJU
- MDW
2 stops9h 10m
Southwest
Deal found 3/5![Southwest logo]()
$632
This Southwest deal was found by Cheapflights users on 3/8. 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 3/318:15 am
MDW
- SJU
2 stops10h 15m
Southwest
Tue 4/72:00 pm
SJU
- MDW
2 stops9h 15m
Southwest
Deal found 3/8![Southwest logo]()
$651
Last-minute flights from Midway to San JuanDiscover last-minute flight deals from Midway to San Juan. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San Juan. Data last updated March 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:42 pm
MDW
- SJU
1 stop26h 37m
Frontier
Mon 4/69:10 pm
SJU
- MDW
2 stops26h 09m
Frontier
Deal found 3/6![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Mon 3/309:42 pm
MDW
- SJU
1 stop26h 37m
Multiple Airlines
Tue 4/712:05 pm
SJU
- MDW
1 stop11h 14m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$247
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:01 am
MDW
- SJU
1 stop10h 28m
Frontier
Thu 4/96:07 pm
SJU
- MDW
1 stop20h 54m
Frontier
Deal found 3/5![Frontier logo]()
$242
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.
Thu 4/92:56 pm
MDW
- SJU
1 stop27h 54m
Multiple Airlines
Thu 5/76:30 am
SJU
- MDW
2 stops16h 51m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$248
This Mytrip deal was found by Cheapflights users on 3/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- SJU
1 stop17h 31m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/9![Frontier logo]()
$208
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
- SJU
1 stop13h 49m
Frontier
Tue 4/143:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Deal found 3/9![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/7. 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.
Sat 4/116:30 am
MDW
- SJU
1 stop14h 03m
Frontier
Mon 4/133:08 am
SJU
- MDW
2 stops17h 23m
Frontier
Deal found 3/7![Frontier logo]()
$241
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:30 am
MDW
- SJU
1 stop13h 30m
Frontier
Sat 4/183:47 pm
SJU
- MDW
1 stop7h 27m
Frontier
Deal found 3/5![Frontier logo]()
$202
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:30 am
MDW
- SJU
1 stop6h 56m
Frontier
Thu 4/163:19 pm
SJU
- MDW
1 stop17h 40m
Frontier
Deal found 3/9![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- SJU
1 stop12h 50m
Multiple Airlines
Wed 4/156:30 am
SJU
- MDW
2 stops16h 44m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$236
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Thu 4/303:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/5![Frontier logo]()
$223
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- SJU
1 stop7h 13m
Frontier
Tue 4/283:08 am
SJU
- MDW
1 stop29h 13m
Frontier
Deal found 3/5![Frontier logo]()
$234
One-way flights from Midway to San JuanSearch for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
Search for one-way flight options from Midway to San Juan. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Trip.com deal was found by Cheapflights users on 3/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- SJU
1 stop16h 23m
Frontier
Deal found 3/6![Frontier logo]()
$100
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
MDW
- SJU
1 stop14h 03m
Frontier
Deal found 3/5![Frontier logo]()
$101
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SJU
1 stop29h 13m
Frontier
Deal found 3/5![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 3/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:10 am
MDW
- SJU
1 stop12h 40m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:34 pm
MDW
- SJU
2 stops39h 59m
Frontier
Deal found 3/6![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 3/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Deal found 3/10![Frontier logo]()
$111
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.
Fri 5/86:00 am
MDW
- SJU
2 stops53h 33m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:42 pm
MDW
- SJU
1 stop26h 37m
Frontier
Deal found 3/8![Frontier logo]()
$118
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Deal found 3/5![Frontier logo]()
$122
Find flight deals from Midway to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Juan (PR1). 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 10, 2026.
Round-trip from | $202 (Priceline) |
|---|---|
One-way from | $100 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $415 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San Juan 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 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/20
6:00 am-4:23 pm
1 stop9h 23m
San Juan Luis Munoz Marin Intl
Wed 4/29
7:30 am-4:26 pm
1 stop9h 56m
$286
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 4/21
12:52 pm-11:12 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Sat 4/25
6:15 am-4:29 pm
1 stop11h 14m
$314
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 6/4
11:35 am-12:25 am
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Sun 6/7
5:20 am-1:05 pm
2 stops8h 45m
$416
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 6/6
12:50 pm-10:20 pm
2 stops8h 30m
San Juan Luis Munoz Marin Intl
Mon 6/8
5:30 am-2:05 pm
2 stops9h 35m
$461
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 5/28
12:50 pm-11:55 pm
2 stops10h 05m
San Juan Luis Munoz Marin Intl
Mon 6/1
2:00 pm-10:20 pm
2 stops9h 20m
$467
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 5/8
9:00 am-8:00 pm
2 stops10h 00m
San Juan Luis Munoz Marin Intl
Mon 5/11
5:35 am-1:10 pm
2 stops8h 35m
$484
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 4/10
12:47 pm-11:15 pm
1 stop9h 28m
San Juan Luis Munoz Marin Intl
Tue 4/14
2:45 pm-10:28 pm
1 stop8h 43m
$542
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 5/21
9:00 am-8:00 pm
2 stops10h 00m
San Juan Luis Munoz Marin Intl
Tue 5/26
2:00 pm-10:15 pm
2 stops9h 15m
$546
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/13
8:35 pm-10:35 am
1 stop13h 00m
San Juan Luis Munoz Marin Intl
Mon 4/20
6:50 am-3:05 pm
2 stops9h 15m
$551
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 3/12
11:35 am-10:55 pm
2 stops10h 20m
San Juan Luis Munoz Marin Intl
Sat 3/14
5:30 am-4:10 pm
1 stop11h 40m
$626
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Midway to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Midway with our price prediction graph.
MDW-PR1
MDW-SJU
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 Juan
MDW-PR1
MDW-SJU
How far ahead should I book a flight from Chicago Midway Airport to San Juan?
Use this chart to determine the optimal time to book a round-trip flight from Midway to San Juan. Price data was last updated on March 6, 2026.
The best time to book flights from Chicago Midway Airport to San Juan is 55 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $91). Flying from Chicago Midway Airport to San Juan in June is currently the most expensive (average of $298). 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 MDW to SJU?
Find hourly flight availability from Midway to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 10, 2026.
When flying from Chicago Midway Airport to San Juan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How often are flights from Chicago to San Juan delayed?
About 29% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 103 minutes.
What is the most punctual flight time for Chicago to San Juan 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.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 29% of flights being delayed.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. 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 Juan. Reviews last updated March 10, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest,Delta, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
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 Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
Alternative routes for Midway to San Juan
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to San Juan by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to San Juan by cabin class
Find flights from Midway to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and San Juan flights
Browse other Midway and San Juan flight options. Last updated on March 10, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on March 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Midway to San Juan
Discover the top 3 airlines that operate flights from Midway to San Juan. 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$494 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$142 | Average$295 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$379 | Average$489 | FlexibilityNo cancel fee | On-time63% |