When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 12 days in advance, which can save you up to 114% on flights from Caribbean to Wisconsin compared to booking the week you need them. Waiting 12 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $220. For sooner than that we have options available in the next 3 days from $510.
February is one of the best times of the year to fly to Wisconsin from Caribbean. Prices for February average $404 per person but you can even find prices for as low as $217. The most expensive prices can be found in the month of June. Opting for a February flight can save you 25% on your journey compared to booking in June
When flying from Caribbean to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$173 - $387
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 8/20
1 stop14h 36m
Chicago O'Hare Intl
Mon 8/26
1 stop17h 37m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 6/18
1 stop18h 22m
Chicago O'Hare Intl
Tue 7/9
1 stop14h 41m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/14
Nonstop4h 59m
Chicago O'Hare Intl
Wed 8/21
1 stop6h 45m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 6/6
1 stop23h 09m
Chicago O'Hare Intl
Mon 6/10
1 stop24h 31m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop8h 15m
Chicago O'Hare Intl
Sat 6/8
2 stops15h 40m
San Juan Luis Munoz Marin IntlMilwaukee-Mitchell
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Tue 8/13
2 stops12h 34m
Milwaukee-Mitchell
Mon 9/9
2 stops12h 17m
San Juan Luis Munoz Marin IntlMinneapolis St Paul
SJU - MSP
SJUMSP
San Juan Luis Munoz Marin Intl
Sat 7/27
Nonstop5h 35m
Minneapolis St Paul
Sat 8/17
Nonstop5h 25m
San Juan Luis Munoz Marin IntlMinneapolis St Paul
SJU - MSP
SJUMSP
San Juan Luis Munoz Marin Intl
Sat 7/20
Nonstop5h 43m
Minneapolis St Paul
Sat 7/27
Nonstop5h 18m
Punta CanaChicago O'Hare Intl
PUJ - ORD
PUJORD
Punta Cana
Wed 10/23
1 stop7h 39m
Chicago O'Hare Intl
Sun 10/27
Nonstop4h 28m
No data available for this route at this time. Please check back soon.
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
Overall
Comfort
Boarding
Crew
Entertainment
Food
Reviews
Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.
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