Cheap Flights from Chicago, IL to San Juan from $114

Return flight: San Juan – Chicago
Cheap Flights Flights Schedule

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 $114, 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.

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

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 $114. The fastest direct flight takes 4h 43m and the fastest connecting – 6h 41m.
Price Departure Arrival Flight Duration Airline Flight
from $114
Find flight
18:23
Chicago
O'Hare International
 00:06+1 день
San Juan
Luis Munoz Marin Intl
 4h 43m Spirit Airlines
NK1635
from $133
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12:03
Chicago
O'Hare International
 17:47
San Juan
Luis Munoz Marin Intl
 4h 44m Spirit Airlines
NK2535
from $199
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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 $121
Find flight
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 $163
Find flight
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 $188
Find flight
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
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on October 09, 2025

The cheapest months to travel to San Juan are july (from 114 $), august (from 114 $), september (from 121 $).

The most expensive months are november (from 282 $), june (from 133 $), february (from 126 $).

What is the lowest airfare Chicago to San Juan?

The cheapest plane ticket found by our users is $114. 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
$114
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Business class
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First class
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Flight Schedule Chicago (Illinois) to San Juan

05:05 — 19:07
13h 2m flight time
Find flight
from$125
05:05 — 09:06 Chicago — Miami
NK2 Spirit Airlines
7h 31m stop
16:37 — 19:07 Miami — San Juan
NK2221 Spirit Airlines
06:00 — 14:15
7h 15m flight time
Find flight
from$121
05:10 — 08:23 Chicago — Atlanta
F91596 Frontier Airlines
1h 30m stop
11:36 — 15:15 Atlanta — San Juan
F92082 Frontier Airlines
06:20 — 14:18
6h 58m flight time
Find flight
from$136
06:20 — 09:39 Chicago — Atlanta
F92292 Frontier Airlines
1h stop
11:36 — 15:15 Atlanta — San Juan
F92082 Frontier Airlines
07:45 — 16:43
7h 58m flight time
Find flight
from$136
07:45 — 10:51 Chicago — Baltimore
F94064 Frontier Airlines
2h stop
12:51 — 16:43 Baltimore — San Juan
F92266 Frontier Airlines
08:52 — 14:44
4h 52m flight time
Find flight
from$207
Chicago — San Juan
UA1996 United Airlines
09:55 — 18:50
7h 55m flight time
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from$125
08:17 — 12:30 Chicago — Miami
NK2193 Spirit Airlines
2h 11m stop
17:28 — 20:02 Miami — San Juan
NK2057 Spirit Airlines
10:00 — 15:51
4h 51m flight time
Find flight
from$114
Chicago — San Juan
NK1530 Spirit Airlines
11:32 — 00:40+1day
12h 8m flight time
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from$122
18:30 — 21:41 Chicago — Raleigh
F93352 Frontier Airlines
6h 39m stop
21:02 — 01:29 Raleigh — San Juan
F91226 Frontier Airlines
12:03 — 17:47
4h 44m flight time
Find flight
from$133
Chicago — San Juan
NK2535 Spirit Airlines
12:51 — 23:54+1day
10h 3m flight time
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from$121
21:12 — 00:57 Chicago — Orlando
F93854 Frontier Airlines
4h 30m stop
17:00 — 19:58 Orlando — San Juan
F93506 Frontier Airlines
12:51 — 02:34+1day
12h 43m flight time
Find flight
from$121
21:12 — 00:57 Chicago — Orlando
F93854 Frontier Airlines
7h 11m stop
23:40 — 02:32 Orlando — San Juan
F94726 Frontier Airlines
14:17 — 20:04
4h 47m flight time
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from$114
Chicago — San Juan
NK491 Spirit Airlines
16:11 — 15:39+1day
22h 28m flight time
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from$126
14:26 — 18:12 Chicago — Tampa
F91186 Frontier Airlines
16h 46m stop
15:12 — 19:17 Tampa — San Juan
F92216 Frontier Airlines
18:03 — 23:54+1day
4h 51m flight time
Find flight
from$199
Chicago — San Juan
UA695 United Airlines
18:23 — 00:06+1day
4h 43m flight time
Find flight
from$114
Chicago — San Juan
NK1635 Spirit Airlines
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 and arrival times - local. Updated on October 9, 2025.

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 $ 121 . And the most expensive tickets are offered by Finnair airline - from $ 1426.

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 $114.

  • UA - United Airlines
    from $199
    Find
  • NK - Spirit Airlines
    from $114
    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 $121.

  • F9 - Frontier Airlines
    from $121
    Find
  • PD - Porter Airlines
    from $345
    Find
  • AV - Avianca
    from $404
    Find
  • SY - Sun Country Airlines
    from $218
    Find
  • AY - Finnair
    from $1426
    Find
  • LF - flynordic
    from $205
    Find
  • UA - United Airlines
    from $208
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  • NK - Spirit Airlines
    from $125
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  • G4 - Allegiant Air
    from $195
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  • TS - Air Transat
    from $359
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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 $114
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  • Midway-MDW
    from $121
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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San Juan airports

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