Cheap Flights from Chicago, IL to San Juan from $41

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On Cheapflightsplus.com you will find 2 direct and 154 connecting flights from Chicago to San Juan. You can compare airfare deals from 7 airlines and multiple travel sites from $41, 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: $41 (one-way), $70 (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 $41. The fastest direct flight takes 4h 48m and the fastest connecting – 6h 10m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $95 Find flight	08:00 Chicago O'Hare International	13:51 San Juan Luis Munoz Marin Intl	4h 51m	Frontier Airlines	F9128
from $129 Find flight	07:49 Chicago O'Hare International	13:37 San Juan Luis Munoz Marin Intl	4h 48m	United Airlines	UA1996
from $41 Find flight	18:15 Chicago O'Hare International	10:54+1 день San Juan Luis Munoz Marin Intl	15h 39m layover 9h 59m - Orlando	Spirit Airlines	NK929 NK1263
from $63 Find flight	10:15 Chicago O'Hare International	19:20 San Juan Luis Munoz Marin Intl	8h 5m layover 2h 25m - Orlando	American Airlines	AA2398 NK1049
from $63 Find flight	11:15 Chicago O'Hare International	22:37 San Juan Luis Munoz Marin Intl	10h 22m layover 4h 53m - Orlando	United Airlines	UA754 NK802
from $72 Find flight	08:20 Chicago O'Hare International	17:27 San Juan Luis Munoz Marin Intl	8h 7m layover 2h 26m - Miami	Spirit Airlines	NK3 B61653
from $72 Find flight	06:40 Chicago Midway	19:29 San Juan Luis Munoz Marin Intl	11h 49m layover 5h 29m - Philadelphia	Southwest Airlines	WN950 F9108
from $72 Find flight	06:00 Chicago Midway	19:20 San Juan Luis Munoz Marin Intl	12h 20m layover 7h 0m - Orlando	Southwest Airlines	WN941 NK1049
from $74 Find flight	18:15 Chicago O'Hare International	09:08+1 день San Juan Luis Munoz Marin Intl	13h 53m layover 8h 13m - Orlando	Spirit Airlines	NK929 B61033
from $90 Find flight	06:00 Chicago O'Hare International	14:48 San Juan Luis Munoz Marin Intl	7h 48m layover 2h 12m - Miami	American Airlines	AA1438 AA1255
from $90 Find flight	08:25 Chicago O'Hare International	22:33 San Juan Luis Munoz Marin Intl	13h 8m layover 7h 21m - Miami	American Airlines	AA1411 AA397
from $79 Find flight	06:40 Chicago Midway	19:20 San Juan Luis Munoz Marin Intl	11h 40m layover 3h 2m - Philadelphia 1h 18m - Orlando	Southwest Airlines	WN950 NK309 NK1049
from $92 Find flight	08:30 Chicago O'Hare International	22:33 San Juan Luis Munoz Marin Intl	13h 3m layover 3h 21m - Newark 1h 42m - Miami	American Airlines	AA1211 AA1060 AA397

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 24, 2024

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	Flight Details	Flight Duration	Price
07:49 — 13:37	07:49 — 13:37 UA1996 United Airlines Chicago — San Juan	4h 48m	Find flight from$129
08:00 — 13:51	08:00 — 13:51 F9128 Frontier Airlines Chicago — San Juan	4h 51m	Find flight from$95
05:00 — 13:04	05:00 — 08:59 AA1163 American Airlines Chicago — Miami 1h 26m stop 10:25 — 13:04 AA1254 American Airlines Miami — San Juan	7h 4m including layover	Find flight from$112
05:00 — 14:48	05:00 — 08:59 AA1163 American Airlines Chicago — Miami 3h 11m stop 12:10 — 14:48 AA1255 American Airlines Miami — San Juan	8h 48m including layover	Find flight from$114
06:00 — 11:56 +1 day	06:00 — 09:30 WN941 Southwest Airlines Chicago — Orlando 23h 26m stop 08:56 — 11:56 F9104 Frontier Airlines Orlando — San Juan	28h 56m including layover	Find flight from$68
06:00 — 19:20	06:00 — 09:30 WN941 Southwest Airlines Chicago — Orlando 7h stop 16:30 — 19:20 NK1049 Spirit Airlines Orlando — San Juan	12h 20m including layover	Find flight from$72
07:15 — 22:25	07:15 — 10:15 AA1666 American Airlines Chicago — Philadelphia 8h stop 18:15 — 22:25 AA1529 American Airlines Philadelphia — San Juan	14h 10m including layover	Find flight from$125
08:20 — 17:27	08:20 — 12:30 NK3 Spirit Airlines Chicago — Miami 2h 26m stop 14:56 — 17:27 B61653 JetBlue Miami — San Juan	8h 7m including layover	Find flight from$72
08:25 — 22:33	08:25 — 12:32 AA1411 American Airlines Chicago — Miami 7h 21m stop 19:53 — 22:33 AA397 American Airlines Miami — San Juan	13h 8m including layover	Find flight from$90
10:15 — 11:56 +1 day	10:15 — 14:05 AA2398 American Airlines Chicago — Orlando 18h 51m stop 08:56 — 11:56 F9104 Frontier Airlines Orlando — San Juan	24h 41m including layover	Find flight from$59
10:15 — 19:20	10:15 — 14:05 AA2398 American Airlines Chicago — Orlando 2h 25m stop 16:30 — 19:20 NK1049 Spirit Airlines Orlando — San Juan	8h 5m including layover	Find flight from$63
11:00 — 22:25	11:00 — 14:10 UA3431 United Airlines Chicago — Philadelphia 4h 5m stop 18:15 — 22:25 AA1529 American Airlines Philadelphia — San Juan	10h 25m including layover	Find flight from$95
11:15 — 22:37	11:15 — 14:55 UA754 United Airlines Chicago — Orlando 4h 53m stop 19:48 — 22:37 NK802 Spirit Airlines Orlando — San Juan	10h 22m including layover	Find flight from$63
12:30 — 22:37	12:30 — 16:10 WN935 Southwest Airlines Chicago — Orlando 3h 38m stop 19:48 — 22:37 NK802 Spirit Airlines Orlando — San Juan	9h 7m including layover	Find flight from$127
13:36 — 22:25	13:36 — 16:49 AA1920 American Airlines Chicago — Philadelphia 1h 26m stop 18:15 — 22:25 AA1529 American Airlines Philadelphia — San Juan	7h 49m including layover	Find flight from$117
13:36 — 12:28 +1 day	13:36 — 16:49 AA1920 American Airlines Chicago — Philadelphia 15h 31m stop 08:20 — 12:28 AA2542 American Airlines Philadelphia — San Juan	21h 52m including layover	Find flight from$130
14:00 — 22:33	14:00 — 18:17 AA791 American Airlines Chicago — Miami 1h 36m stop 19:53 — 22:33 AA397 American Airlines Miami — San Juan	7h 33m including layover	Find flight from$112
14:15 — 01:03 +1 day	14:15 — 17:30 UA555 United Airlines Chicago — Newark 3h 49m stop 21:19 — 01:03 B62889 JetBlue Newark — San Juan	9h 48m including layover	Find flight from$101
15:16 — 12:28 +1 day	15:16 — 18:29 AA1464 American Airlines Chicago — Philadelphia 13h 51m stop 08:20 — 12:28 AA2542 American Airlines Philadelphia — San Juan	20h 12m including layover	Find flight from$130
16:41 — 12:28 +1 day	16:41 — 19:51 AA2853 American Airlines Chicago — Philadelphia 12h 29m stop 08:20 — 12:28 AA2542 American Airlines Philadelphia — San Juan	18h 47m including layover	Find flight from$130
16:41 — 22:25 +1 day	16:41 — 19:51 AA2853 American Airlines Chicago — Philadelphia 22h 24m stop 18:15 — 22:25 AA1529 American Airlines Philadelphia — San Juan	28h 44m including layover	Find flight from$130
17:00 — 09:30 +1 day	17:00 — 21:10 NK425 Spirit Airlines Chicago — Miami 9h 50m stop 07:00 — 09:30 B61053 JetBlue Miami — San Juan	15h 30m including layover	Find flight from$72
18:15 — 10:54 +1 day	18:15 — 22:07 NK929 Spirit Airlines Chicago — Orlando 9h 59m stop 08:06 — 10:54 NK1263 Spirit Airlines Orlando — San Juan	15h 39m including layover	Find flight from$41
18:40 — 15:48 +1 day	18:40 — 21:57 AA2941 American Airlines Chicago — Newark 13h 33m stop 11:30 — 15:48 F9123 Frontier Airlines Newark — San Juan	20h 8m including layover	Find flight from$59
19:55 — 15:48 +1 day	19:55 — 23:10 UA557 United Airlines Chicago — Newark 12h 20m stop 11:30 — 15:48 F9123 Frontier Airlines Newark — San Juan	18h 53m including layover	Find flight from$59
19:55 — 11:30 +1 day	19:55 — 23:10 UA557 United Airlines Chicago — Newark 8h 20m stop 07:30 — 11:30 UA207 United Airlines Newark — San Juan	14h 35m including layover	Find flight from$64
21:24 — 02:11 +2 days	21:24 — 00:49 B6112 JetBlue Chicago — Boston 21h 26m stop 22:15 — 02:11 B661 JetBlue Boston — San Juan	27h 47m including layover	Find flight from$111
07:00 — 22:33	07:00 — 09:21 AA1625 American Airlines Chicago — Dallas 3h 9m stop 12:30 — 16:32 AA2823 American Airlines Dallas — Miami 3h 21m stop 19:53 — 22:33 AA397 American Airlines Miami — San Juan	14h 33m including layover	Find flight from$126
09:28 — 22:33	09:28 — 12:24 AA2895 American Airlines Chicago — Charlotte 2h 16m stop 14:40 — 16:43 AA775 American Airlines Charlotte — Miami 3h 10m stop 19:53 — 22:33 AA397 American Airlines Miami — San Juan	12h 5m including layover	Find flight from$124
12:04 — 22:33	12:04 — 15:04 AA2372 American Airlines Chicago — Charlotte 1h 26m stop 16:30 — 18:43 AA156 American Airlines Charlotte — Miami 1h 10m stop 19:53 — 22:33 AA397 American Airlines Miami — San Juan	9h 29m including layover	Find flight from$124
20:37 — 02:35 +2 days	20:37 — 23:40 NK635 Spirit Airlines Chicago — Atlanta 18h 32m stop 18:12 — 19:52 F91010 Frontier Airlines Atlanta — Orlando 3h 42m stop 23:34 — 02:35 F9106 Frontier Airlines Orlando — San Juan	28h 58m including layover	Find flight from$43
20:37 — 19:20 +1 day	20:37 — 23:40 NK635 Spirit Airlines Chicago — Atlanta 9h 11m stop 08:51 — 10:23 NK1566 Spirit Airlines Atlanta — Orlando 6h 7m stop 16:30 — 19:20 NK1049 Spirit Airlines Orlando — San Juan	21h 43m including layover	Find flight from$57

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on April 24, 2024

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 50m.

The fastest flight 4h 48m
Average flight time 4h 50m
The earliest flight 05:00
The latest flight 21:50
Distance 2060 ml

What is the lowest airfare Chicago to San Juan?

The cheapest plane ticket found by our users is $41. This airfare is for economy class on one-way NK929 flight by Spirit Airlines for August 26, 2020 which leaves O'Hare International in Chicago at 18:15 am and arrives at San Juan Luis Munoz Marin Intl at 10:54.

Economy class

$41

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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 7 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by American Airlines - 70 departures per week at the price of from $ 59 . And the most expensive tickets are offered by United Airlines airline - from $ 1441.

Direct flights

There are 2 nonstop flights on the route. The fastest direct flight is UA1996 by United Airlines takes 4h 48m and the cheapest is NK929 by Spirit Airlines for $95.

F9 - Frontier Airlines

from $95

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UA - United Airlines

from $129

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Connecting Flights

There are 154 flights with layovers on the route. The fastest connecting flight is WN1563 by Southwest Airlines takes 6h 10m and the cheapest is NK929 by Spirit Airlines for $41.

AA - American Airlines

from $59

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F9 - Frontier Airlines

from $90

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B6 - JetBlue

from $111

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WN - Southwest Airlines

from $68

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DL - Delta Air Lines Inc.

from $132

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UA - United Airlines

from $59

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NK - Spirit Airlines

from $41

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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 $41
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Midway-MDW

from $68
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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 7 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737-700

from $64

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Airbus A321-100/200

from $90

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Boeing 737-800

from $90

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Airbus A320

from $95

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Airbus A321

from $112

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Airbus A319

from $117

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Boeing 737-900

from $129

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Airbus A320-100/200

from $130

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Embraer 175 (short wing)

from $138

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Boeing 757-300

from $183

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Top Domestic Destinations from Chicago

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

Chicago — Las Vegas

from $508

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Chicago — Tampa

from $63

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Chicago — Los Angeles

from $181

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Chicago — Orlando

from $62

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Chicago — New York

from $74

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Chicago — Dallas

from $70

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Chicago — San Antonio

from $59

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Chicago — Atlanta

from $76

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Chicago — Miami

from $66

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Chicago — Denver

from $61

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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.

Chicago — London

from $60

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Chicago — Manchester

from $58

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Chicago — Zurich

from $61

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Chicago — Cancun

from $72

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Chicago — Dublin

from $59

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Chicago — Madrid

from $72

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Chicago — Rome

from $79

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Chicago — Paris

from $61

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Chicago — Tel Aviv

from $628

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Chicago — Mumbai

from $74

Find

All flights from Chicago | All flights to San Juan

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»
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