Cheap Flights from Chicago, IL to San Juan from $88
Return flight: San Juan – Chicago
On Cheapflightsplus.com you will find 6 direct and 370 connecting flights from Chicago to San Juan. You can compare airfare deals from 10 airlines and multiple travel sites from $88, 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: $88 (one-way), $151 (round-trip).
Direct flights
Check prices for return flight
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 $88. The fastest direct flight takes 4h 43m and the fastest connecting – 6h 41m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $88 | 18:23 Chicago O'Hare International | 00:06+1 день San Juan Luis Munoz Marin Intl | 4h 43m | Spirit Airlines | NK1635 |
| from $88 | 14:17 Chicago O'Hare International | 20:04 San Juan Luis Munoz Marin Intl | 4h 47m | Spirit Airlines | NK491 |
| from $88 | 10:00 Chicago O'Hare International | 15:51 San Juan Luis Munoz Marin Intl | 4h 51m | Spirit Airlines | NK1530 |
| from $102 | 12:03 Chicago O'Hare International | 17:47 San Juan Luis Munoz Marin Intl | 4h 44m | Spirit Airlines | NK2535 |
| from $154 | 18:03 Chicago O'Hare International | 23:54+1 день San Juan Luis Munoz Marin Intl | 4h 51m | United Airlines | UA695 |
| from $93 | 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 $93 | 12:51 Chicago Midway | 23:54+1 день San Juan Luis Munoz Marin Intl | 10h 3m layover 4h 30m - Orlando | Frontier Airlines | F93854 F93506 |
| from $93 | 12:51 Chicago Midway | 02:34+1 день San Juan Luis Munoz Marin Intl | 12h 43m layover 7h 11m - Orlando | Frontier Airlines | F93854 F94726 |
| from $94 | 11:32 Chicago O'Hare International | 00:40+1 день San Juan Luis Munoz Marin Intl | 12h 8m layover 6h 39m - Raleigh | Frontier Airlines | F93352 F91226 |
| from $97 | 16:11 Chicago Midway | 15:39+1 день San Juan Luis Munoz Marin Intl | 22h 28m layover 16h 46m - Tampa | Frontier Airlines | F91186 F92216 |
| from $105 | 06:20 Chicago Midway | 14:18 San Juan Luis Munoz Marin Intl | 6h 58m layover 1h 0m - Atlanta | Frontier Airlines | F92292 F92082 |
| from $105 | 07:45 Chicago O'Hare International | 16:43 San Juan Luis Munoz Marin Intl | 7h 58m layover 2h 0m - Baltimore | Frontier Airlines | F94064 F92266 |
| from $108 | 16:35 Chicago O'Hare International | 00:54+1 день San Juan Luis Munoz Marin Intl | 7h 19m layover 1h 49m - Orlando | Spirit Airlines | NK2189 NK1989 |
| from $109 | 16:26 Chicago O'Hare International | 15:54+1 день San Juan Luis Munoz Marin Intl | 22h 28m layover 16h 21m - Orlando | Frontier Airlines | F92792 F91824 |
| from $126 | 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 $149 | 15:29 Chicago O'Hare International | 09:56+1 день San Juan Luis Munoz Marin Intl | 17h 27m layover 2h 9m - Miami 8h 0m - Orlando | Spirit Airlines | NK867 NK676 NK3159 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on June 06, 2025
Flight Schedule Chicago (Illinois) to San Juan
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 |
Find flight
from$160 |
|
|
10:00 — 15:51
|
10:00 — 15:51
NK1530
Spirit Airlines
Chicago — San Juan
|
4h 51m |
Find flight
from$88 |
|
|
12:03 — 17:47
|
12:03 — 17:47
NK2535
Spirit Airlines
Chicago — San Juan
|
4h 44m |
Find flight
from$102 |
|
|
14:17 — 20:04
|
14:17 — 20:04
NK491
Spirit Airlines
Chicago — San Juan
|
4h 47m |
Find flight
from$88 |
|
|
18:03 — 23:54
+1 day
|
18:03 — 23:54
UA695
United Airlines
Chicago — San Juan
|
4h 51m |
Find flight
from$154 |
|
|
18:23 — 00:06
+1 day
|
18:23 — 00:06
NK1635
Spirit Airlines
Chicago — San Juan
|
4h 43m |
Find flight
from$88 |
|
|
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$116 |
|
|
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$123 |
|
|
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$93 |
|
|
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$105 |
|
|
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 |
Find flight
from$114 |
|
|
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$105 |
|
|
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 |
Find flight
from$105 |
|
|
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 |
Find flight
from$105 |
|
|
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$123 |
|
|
10:00 — 01:35
+1 day
|
10:00 — 13:39
NK1113
Spirit Airlines
Chicago — Orlando
9h 4m stop
22:43 — 01:35
NK1514
Spirit Airlines
Orlando — San Juan
|
14h 35m including layover |
Find flight
from$124 |
|
|
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$94 |
|
|
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$93 |
|
|
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$93 |
|
|
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$109 |
|
|
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$135 |
|
|
15:29 — 15:41
+1 day
|
15:29 — 19:39
NK867
Spirit Airlines
Chicago — Miami
17h 25m stop
13:04 — 15:41
NK1037
Spirit Airlines
Miami — San Juan
|
23h 12m including layover |
Find flight
from$149 |
|
|
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$97 |
|
|
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$105 |
|
|
17:08 — 23:59
+2 days
|
17:08 — 21:09
F93044
Frontier Airlines
Chicago — Orlando
23h 46m stop
20:55 — 23:59
F91746
Frontier Airlines
Orlando — San Juan
|
29h 51m including layover |
Find flight
from$125 |
|
|
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$109 |
|
|
18:34 — 15:41
+1 day
|
18:34 — 22:32
NK1027
Spirit Airlines
Chicago — Miami
14h 32m stop
13:04 — 15:41
NK1037
Spirit Airlines
Miami — San Juan
|
20h 7m including layover |
Find flight
from$149 |
|
|
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 |
Find flight
from$109 |
|
|
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$109 |
|
|
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$125 |
|
|
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$126 |
|
|
15:29 — 09:56
+1 day
|
15:29 — 19:39
NK867
Spirit Airlines
Chicago — Miami
2h 9m stop
21:48 — 23:00
NK676
Spirit Airlines
Miami — Orlando
8h stop
07:00 — 09:56
NK3159
Spirit Airlines
Orlando — San Juan
|
17h 27m including layover |
Find flight
from$149 |
|
|
21:10 — 19:19
+1 day
|
20:15 — 22:57
NK2047
Spirit Airlines
Chicago — Dallas
5h 47m stop
05:45 — 09:40
NK2199
Spirit Airlines
Dallas — Miami
7h 25m stop
16:37 — 19:07
NK2221
Spirit Airlines
Miami — San Juan
|
21h 9m including layover |
Find flight
from$141 |
|
*Departure and arrival times - local. Updated on June 6, 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 118 $), august (from 118 $), september (from 125 $).
The most expensive months are november (from 292 $), october (from 153 $), june (from 130 $).
What is the lowest airfare Chicago to San Juan?
The cheapest plane ticket found by our users is $88. This airfare is for economy class on one-way NK1635 flight by Spirit Airlines for July 14, 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
$88
Business class
?
First class
?
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 - 20 departures per week at the price of from $ 93 . And the most expensive tickets are offered by Finnair airline - from $ 1107.
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 $88.
- UA - United Airlinesfrom $154Find
- NK - Spirit Airlinesfrom $88Find
See more direct flights
Connecting Flights
There are 370 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 $93.
- F9 - Frontier Airlinesfrom $93Find
- PD - Porter Airlinesfrom $267Find
- AV - Aviancafrom $314Find
- SY - Sun Country Airlinesfrom $169Find
- AY - Finnairfrom $1107Find
- LF - flynordicfrom $159Find
- UA - United Airlinesfrom $161Find
- NK - Spirit Airlinesfrom $108Find
- G4 - Allegiant Airfrom $151Find
- TS - Air Transatfrom $279Find
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-ORDfrom $88Find
- Midway-MDWfrom $93Find
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
San Juan airports
- Isla Grande-SIGFind
- Luis Munoz Marin Intl-SJUFind
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.
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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.
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How to book a plane 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.