Cheap Flights from Chicago, IL to San Juan from $113

Return flight: San Juan – Chicago
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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 $113, 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: $113 (one-way), $194 (round-trip).
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Best Flights from Chicago to San Juan Today

Take a look at the list of non stop flights and flights with layovers from Chicago to San Juan with the lowest price of $113. The fastest direct flight takes 4h 43m and the fastest connecting – 6h 41m.
Price Departure Arrival Flight Duration Airline Flight
from $113
Find flight
18:23
Chicago
O'Hare International
 00:06+1 день
San Juan
Luis Munoz Marin Intl
 4h 43m Spirit Airlines
NK1635
from $132
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12:03
Chicago
O'Hare International
 17:47
San Juan
Luis Munoz Marin Intl
 4h 44m Spirit Airlines
NK2535
from $198
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18:03
Chicago
O'Hare International
 23:54+1 день
San Juan
Luis Munoz Marin Intl
 4h 51m United Airlines
UA695
from $120
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06:00
Chicago
O'Hare International
 14:15
San Juan
Luis Munoz Marin Intl
 7h 15m
layover
1h 30m - Atlanta
 Frontier Airlines
F91596
F92082
from $125
Find flight
09:55
Chicago
O'Hare International
 18:50
San Juan
Luis Munoz Marin Intl
 7h 55m
layover
2h 11m - Miami
 Spirit Airlines
NK2193
NK2057
from $162
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11:21
Chicago
O'Hare International
 10:06+1 день
San Juan
Luis Munoz Marin Intl
 21h 45m
layover
5h 39m - Dallas
8h 10m - Miami
 Spirit Airlines
NK1633
NK1395
NK1396
from $187
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12:45
Chicago
O'Hare International
 09:43+1 день
San Juan
Luis Munoz Marin Intl
 19h 58m
layover
3h 57m - Houston
6h 9m - Philadelphia
 Spirit Airlines
NK2576
NK2231
NK2303
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 18, 2025
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
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$125
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
Find flight
from$120
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
Find flight
from$135
07:45 — 16:43
07:45 — 10:51 F94064 Frontier Airlines
Chicago — Baltimore
2h stop
12:51 — 16:43 F92266 Frontier Airlines
Baltimore — San Juan
7h 58m
including layover
Find flight
from$135
08:52 — 14:44
08:52 — 14:44 UA1996 United Airlines
Chicago — San Juan
4h 52m
Find flight
from$206
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
Find flight
from$125
10:00 — 15:51
10:00 — 15:51 NK1530 Spirit Airlines
Chicago — San Juan
4h 51m
Find flight
from$113
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
Find flight
from$121
12:03 — 17:47
12:03 — 17:47 NK2535 Spirit Airlines
Chicago — San Juan
4h 44m
Find flight
from$132
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$120
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$120
14:17 — 20:04
14:17 — 20:04 NK491 Spirit Airlines
Chicago — San Juan
4h 47m
Find flight
from$113
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
Find flight
from$125
18:03 — 23:54
+1 day
18:03 — 23:54 UA695 United Airlines
Chicago — San Juan
4h 51m
Find flight
from$198
18:23 — 00:06
+1 day
18:23 — 00:06 NK1635 Spirit Airlines
Chicago — San Juan
4h 43m
Find flight
from$113
*Departure and arrival times - local. Updated on September 18, 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 113 $), august (from 113 $), september (from 120 $).

The most expensive months are november (from 281 $), october (from 147 $), june (from 132 $).

What is the lowest airfare Chicago to San Juan?

The cheapest plane ticket found by our users is $113. This airfare is for economy class on one-way NK1635 flight by Spirit Airlines for August 8, 2025 which leaves O'Hare International in Chicago at 18:23 am and arrives at San Juan Luis Munoz Marin Intl at 00:06.

Economy class
$113
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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 $ 120 . And the most expensive tickets are offered by Finnair airline - from $ 1418.

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 NK1635 by Spirit Airlines for $113.

  • UA - United Airlines
    from $198
    Find
  • NK - Spirit Airlines
    from $113
    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 NK1635 by Spirit Airlines for $120.

  • F9 - Frontier Airlines
    from $120
    Find
  • PD - Porter Airlines
    from $343
    Find
  • AV - Avianca
    from $402
    Find
  • SY - Sun Country Airlines
    from $217
    Find
  • AY - Finnair
    from $1418
    Find
  • LF - flynordic
    from $204
    Find
  • UA - United Airlines
    from $206
    Find
  • NK - Spirit Airlines
    from $125
    Find
  • G4 - Allegiant Air
    from $193
    Find
  • TS - Air Transat
    from $357
    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 $113
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  • Midway-MDW
    from $120
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • 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

Airplanes

There are flights to San Juan from Chicago by 10 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Chicago

You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.

Top International Destinations from Chicago

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

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.

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