Cheap Flights from Chicago, IL to San Juan from $120

Return flight: San Juan – Chicago

On Cheapflightsplus.com you will find 6 direct and 454 connecting flights from Chicago to San Juan. You can compare airfare deals from 10 airlines and multiple travel sites from $120, book and save on cheap plane tickets and last minute offers. Also check out CHI-SJU flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Chicago to San Juan Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $120 (one-way), $206 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from Chicago to San Juan. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
08:52 — 14:44
08:52 — 14:44 UA1996 United Airlines
Chicago — San Juan
4h 52m
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from$219
10:00 — 15:51
10:00 — 15:51 NK1530 Spirit Airlines
Chicago — San Juan
4h 51m
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from$120
12:03 — 17:47
12:03 — 17:47 NK2535 Spirit Airlines
Chicago — San Juan
4h 44m
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from$140
14:17 — 20:04
14:17 — 20:04 NK491 Spirit Airlines
Chicago — San Juan
4h 47m
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from$120
18:03 — 23:54
+1 day
18:03 — 23:54 UA695 United Airlines
Chicago — San Juan
4h 51m
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from$258
18:23 — 00:06
+1 day
18:23 — 00:06 NK1635 Spirit Airlines
Chicago — San Juan
4h 43m
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from$176
05:05 — 19:07
05:05 — 09:06 NK2 Spirit Airlines
Chicago — Miami
7h 31m stop
16:37 — 19:07 NK2221 Spirit Airlines
Miami — San Juan
13h 2m
including layover
Find flight
from$132
05:05 — 19:19
05:05 — 09:12 NK1 Spirit Airlines
Chicago — Miami
7h 33m stop
16:45 — 19:19 NK2221 Spirit Airlines
Miami — San Juan
13h 14m
including layover
Find flight
from$158
06:00 — 14:15
05:10 — 08:23 F91596 Frontier Airlines
Chicago — Atlanta
1h 30m stop
11:36 — 15:15 F92082 Frontier Airlines
Atlanta — San Juan
7h 15m
including layover
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from$127
06:20 — 14:18
06:20 — 09:39 F92292 Frontier Airlines
Chicago — Atlanta
1h stop
11:36 — 15:15 F92082 Frontier Airlines
Atlanta — San Juan
6h 58m
including layover
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from$144
07:15 — 01:11
+1 day
07:15 — 11:03 NK3200 Spirit Airlines
Chicago — Orlando
11h 14m stop
22:17 — 01:11 NK3166 Spirit Airlines
Orlando — San Juan
16h 56m
including layover
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from$156
07:56 — 16:17
07:47 — 11:26 NK2550 Spirit Airlines
Chicago — Orlando
1h 48m stop
22:09 — 00:54 NK1989 Spirit Airlines
Orlando — San Juan
7h 21m
including layover
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from$168
08:35 — 00:32
+1 day
08:35 — 12:20 F91458 Frontier Airlines
Chicago — Orlando
9h 6m stop
21:26 — 00:32 F91746 Frontier Airlines
Orlando — San Juan
14h 57m
including layover
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from$144
08:35 — 02:39
+1 day
08:35 — 12:20 F91458 Frontier Airlines
Chicago — Orlando
11h 20m stop
23:40 — 02:39 F94726 Frontier Airlines
Orlando — San Juan
17h 4m
including layover
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from$144
09:55 — 18:50
08:17 — 12:30 NK2193 Spirit Airlines
Chicago — Miami
2h 11m stop
17:28 — 20:02 NK2057 Spirit Airlines
Miami — San Juan
7h 55m
including layover
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from$132
09:58 — 20:25
09:17 — 13:11 F92792 Frontier Airlines
Chicago — Orlando
3h 41m stop
17:00 — 19:58 F93506 Frontier Airlines
Orlando — San Juan
9h 27m
including layover
Find flight
from$165
10:19 — 22:27
10:33 — 13:19 NK2440 Spirit Airlines
Chicago — Baltimore
5h 32m stop
19:06 — 22:53 NK2533 Spirit Airlines
Baltimore — San Juan
11h 8m
including layover
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from$168
11:32 — 00:40
+1 day
18:30 — 21:41 F93352 Frontier Airlines
Chicago — Raleigh
6h 39m stop
21:02 — 01:29 F91226 Frontier Airlines
Raleigh — San Juan
12h 8m
including layover
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from$144
12:51 — 23:54
+1 day
21:12 — 00:57 F93854 Frontier Airlines
Chicago — Orlando
4h 30m stop
17:00 — 19:58 F93506 Frontier Airlines
Orlando — San Juan
10h 3m
including layover
Find flight
from$127
12:51 — 02:34
+1 day
21:12 — 00:57 F93854 Frontier Airlines
Chicago — Orlando
7h 11m stop
23:40 — 02:32 F94726 Frontier Airlines
Orlando — San Juan
12h 43m
including layover
Find flight
from$127
13:03 — 01:11
+1 day
13:03 — 16:51 NK1108 Spirit Airlines
Chicago — Orlando
5h 26m stop
22:17 — 01:11 NK3166 Spirit Airlines
Orlando — San Juan
11h 8m
including layover
Find flight
from$149
13:03 — 09:56
+1 day
13:03 — 16:51 NK1108 Spirit Airlines
Chicago — Orlando
14h 9m stop
07:00 — 09:56 NK3159 Spirit Airlines
Orlando — San Juan
19h 53m
including layover
Find flight
from$184
14:53 — 23:07
+1 day
14:53 — 17:46 F93088 Frontier Airlines
Chicago — Baltimore
1h 34m stop
19:20 — 23:07 F92266 Frontier Airlines
Baltimore — San Juan
7h 14m
including layover
Find flight
from$155
16:11 — 15:39
+1 day
14:26 — 18:12 F91186 Frontier Airlines
Chicago — Tampa
16h 46m stop
15:12 — 19:17 F92216 Frontier Airlines
Tampa — San Juan
22h 28m
including layover
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from$133
16:37 — 00:32
+1 day
09:17 — 13:11 F92792 Frontier Airlines
Chicago — Orlando
47m stop
21:26 — 00:21 F91746 Frontier Airlines
Orlando — San Juan
6h 55m
including layover
Find flight
from$144
17:14 — 02:32
+1 day
17:14 — 21:11 F93044 Frontier Airlines
Chicago — Orlando
2h 29m stop
23:40 — 02:32 F94726 Frontier Airlines
Orlando — San Juan
8h 18m
including layover
Find flight
from$155
17:38 — 10:06
+1 day
17:38 — 21:48 NK1106 Spirit Airlines
Chicago — Miami
9h 52m stop
07:40 — 10:06 NK1396 Spirit Airlines
Miami — San Juan
15h 28m
including layover
Find flight
from$149
18:16 — 15:39
+1 day
13:02 — 16:48 F91416 Frontier Airlines
Chicago — Tampa
14h 38m stop
14:45 — 17:45 F92216 Frontier Airlines
Tampa — San Juan
20h 23m
including layover
Find flight
from$171
19:00 — 12:47
+1 day
19:00 — 21:35 NK824 Spirit Airlines
Chicago — Dallas
9h 25m stop
07:00 — 12:47 NK3707 Spirit Airlines
Dallas — San Juan
16h 47m
including layover
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from$149
19:39 — 09:56
+1 day
19:39 — 23:32 NK507 Spirit Airlines
Chicago — Orlando
7h 28m stop
07:00 — 09:56 NK3159 Spirit Airlines
Orlando — San Juan
13h 17m
including layover
Find flight
from$149
20:55 — 11:23
+1 day
20:55 — 23:59 F94368 Frontier Airlines
Chicago — Philadelphia
7h 31m stop
07:30 — 11:23 F91016 Frontier Airlines
Philadelphia — San Juan
13h 28m
including layover
Find flight
from$155
21:12 — 23:59
+2 days
21:12 — 00:57 F93854 Frontier Airlines
Chicago — Orlando
20h 7m stop
21:04 — 23:59 F92982 Frontier Airlines
Orlando — San Juan
25h 47m
including layover
Find flight
from$160
21:12 — 23:59
+2 days
21:12 — 00:57 F93854 Frontier Airlines
Chicago — Orlando
20h 2m stop
21:26 — 00:21 F91746 Frontier Airlines
Orlando — San Juan
25h 47m
including layover
Find flight
from$161
11:21 — 10:06
+1 day
11:21 — 13:51 NK1633 Spirit Airlines
Chicago — Dallas
5h 39m stop
19:30 — 23:30 NK1395 Spirit Airlines
Dallas — Miami
8h 10m stop
07:40 — 10:06 NK1396 Spirit Airlines
Miami — San Juan
21h 45m
including layover
Find flight
from$172
*Departure and arrival times - local. Updated on August 8, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to San Juan depends on and how to choose the most interesting flight option for you.

Distance between Chicago and San Juan is 3314 miles. Time difference between the cities is 2h. Airplanes depart 05:00 to 21:50 from 7 Chicago airports and arrive 05:00 to 21:50 to 2 San Juan airports. Average flight time is 4h 49m.

  • The fastest flight 4h 43m
  • Average flight time 4h 49m
  • The earliest flight 05:00
  • The latest flight 21:50
  • Distance 2060 ml

The cheapest months to travel to San Juan are july (from 120 $), august (from 120 $), september (from 127 $).

The most expensive months are november (from 298 $), october (from 156 $), june (from 140 $).

What is the lowest airfare Chicago to San Juan?

The cheapest plane ticket found by our users is $120. This airfare is for economy class on one-way NK1530 flight by Spirit Airlines for August 16, 2025 which leaves O'Hare International in Chicago at 10:00 am and arrives at San Juan Luis Munoz Marin Intl at 15:51.

Economy class
$120
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Business class
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First class
?
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Popular Airlines on the Route

The flight Chicago — San Juan is served by 10 regular airlines and 6 low-cost airlines. Most of the flights on this route are operated by Frontier Airlines - 34 departures per week at the price of from $ 127 . And the most expensive tickets are offered by Finnair airline - from $ 1507.

Direct flights

There are 6 nonstop flights on the route. The fastest direct flight is NK1635 by Spirit Airlines takes 4h 43m and the cheapest is NK1530 by Spirit Airlines for $120.

  • UA - United Airlines
    from $219
    Find
  • NK - Spirit Airlines
    from $120
    Find
See more direct flights

Connecting Flights

There are 454 flights with layovers on the route. The fastest connecting flight is NK1986 by Spirit Airlines takes 6h 41m and the cheapest is NK1530 by Spirit Airlines for $127.

  • F9 - Frontier Airlines
    from $127
    Find
  • PD - Porter Airlines
    from $364
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  • AV - Avianca
    from $427
    Find
  • SY - Sun Country Airlines
    from $230
    Find
  • AY - Finnair
    from $1507
    Find
  • LF - flynordic
    from $217
    Find
  • UA - United Airlines
    from $219
    Find
  • NK - Spirit Airlines
    from $132
    Find
  • G4 - Allegiant Air
    from $206
    Find
  • TS - Air Transat
    from $380
    Find
See more connecting flights

Airports

You can fly from Chicago to San Juan from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $120
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  • Midway-MDW
    from $127
    Find
  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

San Juan airports

  • Isla Grande-SIG
    Find
  • Luis Munoz Marin Intl-SJU
    Find

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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