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Stops
- Up to 1 stop$950
Airlines
- American Airlines$950
Cabin Class
- First$950
- Business$993
Departure Airports
- Luis Munoz Marin International Airport$950
Arrival Airports
- Chicago O Hare Airport$950
Layover Airports
- Charlotte Douglas International Airport$993
- Miami International Airport$950
- Philadelphia International Airport$1100
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05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$950
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$984
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$993
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$993
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$1027
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$1027
Free cancellation within 83 hours of booking
05/29/25
SJU
6h 53m
CLT
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$1064
Free cancellation within 83 hours of booking
05/29/25
SJU
5h 20m
Direct
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$1090
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
13h 46m
CLT
06/06/25
SJU
$1100
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1100
Free cancellation within 83 hours of booking
05/29/25
SJU
6h 53m
CLT
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$1107
Free cancellation within 83 hours of booking
05/29/25
SJU
6h 53m
CLT
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$1107
Free cancellation within 83 hours of booking
05/29/25
SJU
5h 20m
Direct
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$1133
Free cancellation within 83 hours of booking
05/29/25
SJU
5h 20m
Direct
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$1133
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
13h 46m
CLT
06/06/25
SJU
$1134
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1134
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
8h 31m
CLT
06/05/25
SJU
$1167
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
6h 50m
CLT
06/05/25
SJU
$1167
Free cancellation within 83 hours of booking
05/29/25
SJU
10h 55m
MIA
05/29/25
ORD
06/05/25
ORD
6h 23m
CLT
06/06/25
SJU
$1167
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
11h 5m
MIA
06/05/25
SJU
$1174
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
6h 23m
CLT
06/06/25
SJU
$1201
Free cancellation within 83 hours of booking
05/29/25
SJU
7h 26m
MIA
05/29/25
ORD
06/05/25
ORD
6h 50m
CLT
06/05/25
SJU
$1201
Free cancellation within 83 hours of booking
05/29/25
SJU
6h 53m
CLT
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1214
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
12h 5m
MIA
06/05/25
SJU
$1217
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
10h 20m
CLT
06/06/25
SJU
$1217
Free cancellation within 83 hours of booking
05/29/25
SJU
5h 20m
Direct
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1239
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
13h 46m
CLT
06/06/25
SJU
$1324
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
13h 9m
PHL
06/05/25
SJU
$1324
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
6h 50m
CLT
06/05/25
SJU
$1391
Free cancellation within 83 hours of booking
05/29/25
SJU
8h 16m
PHL
05/29/25
ORD
06/05/25
ORD
8h 31m
CLT
06/05/25
SJU
$1391
Free cancellation within 83 hours of booking
Top Deals on flights Business Class from San Juan to Chicago
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
9h 21m
CLT
May 30
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
10h 55m
MIA
May 29
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
10h 41m
CLT
May 30
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
13h 1m
MIA
May 29
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
12h 1m
CLT
May 30
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
8h 13m
MIA
May 29
ORD
as low as
$448
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
13h 4m
PHL
May 29
ORD
as low as
$521
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
5h 20m
Direct
May 29
ORD
as low as
$588
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
8h 56m
JFK
May 29
ORD
as low as
$588
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
9h 27m
PHL
May 29
ORD
as low as
$672
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
8h 16m
PHL
May 29
ORD
as low as
$672
San Juan, PR (SJU) - Chicago, US (CHI)
May 29
SJU
9h 49m
DFW
May 29
ORD
as low as
$797
Frequently Asked Questions
What is the time difference between destination and arrival?
The time difference between San Juan and Chicago is typically one hour, with Chicago being one hour ahead of San Juan.
Is there a direct flight from origin to destination?
Yes, there are direct flights from Luis Munoz Marin International Airport to Chicago O Hare Airport. Spirit Airlines offers a flight for $221 with a duration of 4 hours 16 minutes. United Airlines provides a faster option for $400 with a duration of 4 hours 10 minutes. American Airlines also offers a flight for $486.
Are there convenient layover flights from San Juan to Chicago?
Yes, there are convenient layover flights available from San Juan to Chicago. Airlines with one stop options include Frontier Airlines at $307, Spirit Airlines at $369, United Airlines at $380, Delta Air Lines at $410, and American Airlines at $460. Two stop options include JetBlue at $572 and United Airlines at $578.
What are the most convenient layover airports for my flight from San Juan to Chicago?
Consider layovers at Orlando International Airport, George Bush Intercontinental Houston Airport, Hartsfield Jackson Atlanta International Airport, Newark Liberty Airport, and New York John F Kennedy Airport for your flight.
What is the cheapest and fastest flight from San Juan to Chicago?
The cheapest flight is with Spirit Airlines at $221, taking 4 hours 16 minutes. The fastest flight is with United Airlines at $400, taking 4 hours 10 minutes.
What are all possible destination arrival airports?
The destination arrival airport for your flight is Chicago O'Hare Airport.
Flights to Chicago
Return flights
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