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Cheap flights from Chicago to San Juan

32 nonstop flights a week, 3 of them today. Operated by 4 airlines, about 4h 44m in the air, 2,054 mi (3,305 km). Tickets from $120, nonstop from $131.

Flights from Chicago to San Juan

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Filters

Best fares from Chicago to San Juan

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $120 13 January 2027, with a connection Cheapest nonstop $131 13 January 2027, Frontier Airlines Cheapest month January 2027 tickets from $120

Chicago to San Juan at a glance

flight time, from 4h 35m to 4h 58m
4h 44m
straight-line distance
2,054 mi (3,305 km)
flights a week
32
flights today
3
first and last departure
08:05 - 23:53
lowest price, with a connection, 13 January
$120
lowest nonstop price
$131
airlines
4

Chicago to San Juan ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: January 2027, tickets from $120. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is December 2026: from $173. The average across months is $146.

Chicago to San Juan flight schedule

32 flights a week, 3 today, 27 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
AA 2279
American Airlines
08:05 , terminal 3
14:55 Luis Munoz Marin International, terminal C
4h 50m
Daily
Boeing 737-800
AA 3096
American Airlines
08:05 , terminal 3
14:48 Luis Munoz Marin International, terminal C
4h 43m
Mon, Thu, Fri, Sat, Sun
Boeing 737-800
WN 1590
Southwest Airlines
08:15 Chicago Midway International
15:00 Luis Munoz Marin International, terminal B
4h 45m
Sat
Boeing 737
UA 1996
United Airlines
08:52 , terminal 1
15:40 Luis Munoz Marin International, terminal B
4h 48m
Daily
Airbus A320
WN 726
Southwest Airlines
08:55 Chicago Midway International
15:35 Luis Munoz Marin International, terminal B
4h 40m
Sat
UA 695
United Airlines
14:16 , terminal 1
21:00 Luis Munoz Marin International, terminal B
4h 44m
Daily
Airbus A320
F9 3346
Frontier Airlines
23:53 , terminal 5
06:32 Luis Munoz Marin International
4h 39m
Mon, Fri, Sat, Sun
Airbus A320

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 2 December.

FlightDepartsArrivesDurationDaysAircraft
AA 2213
American Airlines
08:15 , terminal 3
14:53 Luis Munoz Marin International, terminal C
4h 38m
Seasonal
Boeing 737-800
AA 2213
American Airlines
08:13 , terminal 3
14:51 Luis Munoz Marin International, terminal C
4h 38m
Seasonal
Boeing 737-800
AA 3176
American Airlines
08:12 , terminal 3
15:00 Luis Munoz Marin International, terminal C
4h 48m
Seasonal
Boeing 737
AA 2571
American Airlines
23:00 , terminal 3
05:36 Luis Munoz Marin International, terminal C
4h 36m
Seasonal
Boeing 737-800
F9 3346
Frontier Airlines
23:50 , terminal 5
06:36 Luis Munoz Marin International
4h 46m
Seasonal
Airbus A320
AA 3176
American Airlines
08:15 , terminal 3
14:53 Luis Munoz Marin International, terminal C
4h 38m
Seasonal
Boeing 737-800
AA 2571
American Airlines
18:24 , terminal 3
01:05 Luis Munoz Marin International, terminal C
4h 41m
Seasonal
Boeing 737-800
F9 3346
Frontier Airlines
00:17 , terminal 5
07:03 Luis Munoz Marin International
4h 46m
Seasonal
Airbus A320
AA 3276
American Airlines
08:05 , terminal 3
14:51 Luis Munoz Marin International, terminal C
4h 46m
Seasonal
Boeing 737-800
AA 1555
American Airlines
17:01 , terminal 3
23:41 Luis Munoz Marin International, terminal C
4h 40m
Seasonal
Boeing 737-800
UA 795
United Airlines
07:35 , terminal 1
14:18 Luis Munoz Marin International, terminal B
4h 43m
Seasonal
Boeing 737
WN 3411
Southwest Airlines
07:50 Chicago Midway International
14:25 Luis Munoz Marin International, terminal B
4h 35m
Seasonal
Boeing 737
AA 2988
American Airlines
19:08 , terminal 3
01:47 Luis Munoz Marin International, terminal C
4h 39m
Seasonal
Boeing 737-800
WN 2659
Southwest Airlines
07:45 Chicago Midway International
14:20 Luis Munoz Marin International, terminal B
4h 35m
Seasonal
Boeing 737
WN 2856
Southwest Airlines
07:55 Chicago Midway International
14:40 Luis Munoz Marin International, terminal B
4h 45m
Seasonal
Boeing 737
WN 865
Southwest Airlines
08:10 Chicago Midway International
13:55 Luis Munoz Marin International, terminal B
4h 45m
Selected dates
Boeing 737
UA 1996
United Airlines
08:49 , terminal 1
14:44 Luis Munoz Marin International, terminal B
4h 55m
Seasonal
Boeing 737
UA 695
United Airlines
14:38 , terminal 1
20:34 Luis Munoz Marin International, terminal B
4h 56m
Seasonal
Boeing 737
AA 2845
American Airlines
08:32 , terminal 3
14:20 Luis Munoz Marin International, terminal C
4h 48m
Seasonal
Airbus A321
WN 2463
Southwest Airlines
08:00 Chicago Midway International
13:40 Luis Munoz Marin International, terminal B
4h 40m
Seasonal
Boeing 737
AA 2845
American Airlines
18:06 , terminal 3
23:59 Luis Munoz Marin International, terminal C
4h 53m
Seasonal
Boeing 737-800
AA 3169
American Airlines
18:20 , terminal 3
23:59 Luis Munoz Marin International, terminal C
4h 39m
Seasonal
Boeing 737-800
WN 2550
Southwest Airlines
07:45 Chicago Midway International
13:25 Luis Munoz Marin International, terminal B
4h 40m
Seasonal
Boeing 737
WN 2663
Southwest Airlines
07:45 Chicago Midway International
13:25 Luis Munoz Marin International, terminal B
4h 40m
Seasonal
Boeing 737
AA 3169
American Airlines
17:50 , terminal 3
23:48 Luis Munoz Marin International, terminal C
4h 58m
Seasonal
Boeing 737-800
UA 1996
United Airlines
08:55 , terminal 1
14:44 Luis Munoz Marin International, terminal B
4h 49m
Seasonal
Boeing 737
AA 3169
American Airlines
17:20 , terminal 3
23:15 Luis Munoz Marin International, terminal C
4h 55m
Seasonal
Boeing 737-800

Days of the week are taken from the schedule for the next 14 days; schedules change by season. San Juan is 2 hours ahead of Chicago. The search shows seat availability and the price for your date.

Airlines flying Chicago to San Juan

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

United Airlines14 a week American Airlines12 a week Frontier Airlines4 a week Southwest Airlines2 a week

Airports

Where flights from Chicago to San Juan depart and land

Departure from Chicago

Chicago Midway International MDW

2 flights a week, 9 mi (14 km) from the city centre

About the airport

Arrival in San Juan

Luis Munoz Marin International SJU

32 flights a week, terminals B, C, 7 mi (11 km) from the city centre

About the airport

Frequently asked questions

How long is the flight from Chicago to San Juan?
A nonstop flight takes 4 hours 44 minutes on average, from 4h 35m to 4h 58m depending on the flight.
How far is San Juan from Chicago?
2,054 mi (3,305 km) in a straight line between the cities.
Which airlines fly nonstop from Chicago to San Juan?
United Airlines (14 a week), American Airlines (12 a week), Frontier Airlines (4 a week) and Southwest Airlines (2 a week).
How many flights a day are there from Chicago to San Juan?
3 flights today and 32 a week, about 4.6 a day on average.
When are the first and last flights from Chicago to San Juan?
The first departure is at 08:05 (AA2279), the last at 23:53 (F93346). Local time.
What is the cheapest month to fly from Chicago to San Juan?
January 2027: tickets from $120. The most expensive is December 2026, from $173.
What is the cheapest upcoming date to fly from Chicago to San Juan?
13 January 2027 (Wednesday): from $120 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Chicago to San Juan?
Frontier Airlines: nonstop tickets from $131 on 13 January by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Chicago and San Juan?
San Juan is 2 hours ahead of Chicago. Schedule times on this page are local to each airport.
Which Chicago airport do flights to San Juan leave from?
Chicago Midway International (2 a week).