Cheap Flights from San Juan to Chicago, IL from $73

Return flight: Chicago – San Juan

On Cheapflightsplus.com you will find 7 direct and 270 connecting flights from San Juan to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $73, book and save on cheap plane tickets and last minute offers. Also check out SJU-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip San Juan to Chicago 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: $73 (one-way), $125 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from San Juan to Chicago. 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
08:35 — 11:54
08:35 — 11:54 UA2089 United Airlines
San Juan — Chicago
5h 19m
Find flight
from$274
14:17 — 17:47
14:17 — 17:47 NK851 Spirit Airlines
San Juan — Chicago
5h 30m
Find flight
from$111
16:00 — 19:26
16:00 — 19:26 NK518 Spirit Airlines
San Juan — Chicago
5h 26m
Find flight
from$356
16:52 — 20:11
16:52 — 20:11 UA2088 United Airlines
San Juan — Chicago
5h 19m
Find flight
from$270
17:41 — 20:44
17:41 — 20:44 NK1531 Spirit Airlines
San Juan — Chicago
5h 3m
Find flight
from$107
21:26 — 00:51
+1 day
21:26 — 00:51 NK173 Spirit Airlines
San Juan — Chicago
5h 25m
Find flight
from$107
21:59 — 00:58
+1 day
21:59 — 00:58 NK492 Spirit Airlines
San Juan — Chicago
4h 59m
Find flight
from$107
02:25 — 10:09
02:25 — 05:33 F94461 Frontier Airlines
San Juan — Philadelphia
3h 23m stop
08:56 — 10:09 F91617 Frontier Airlines
Philadelphia — Chicago
9h 44m
including layover
Find flight
from$90
03:59 — 12:05
03:59 — 06:09 F91823 Frontier Airlines
San Juan — Orlando
3h 47m stop
09:56 — 12:05 F93043 Frontier Airlines
Orlando — Chicago
10h 6m
including layover
Find flight
from$89
04:08 — 12:23
03:59 — 06:09 F91823 Frontier Airlines
San Juan — Orlando
4h 17m stop
06:00 — 07:55 F91457 Frontier Airlines
Orlando — Chicago
10h 15m
including layover
Find flight
from$95
06:00 — 11:41
11:45 — 14:05 F93979 Frontier Airlines
San Juan — Tampa
1h 35m stop
09:54 — 11:41 F91185 Frontier Airlines
Tampa — Chicago
7h 41m
including layover
Find flight
from$74
06:20 — 17:12
06:20 — 09:32 F92871 Frontier Airlines
San Juan — Atlanta
6h 40m stop
16:18 — 17:18 F92143 Frontier Airlines
Atlanta — Chicago
12h 52m
including layover
Find flight
from$89
08:00 — 00:59
+1 day
15:03 — 17:27 F92249 Frontier Airlines
San Juan — Orlando
12h 43m stop
07:30 — 09:54 F93043 Frontier Airlines
Orlando — Chicago
18h 59m
including layover
Find flight
from$96
10:34 — 18:50
11:12 — 13:29 NK3160 Spirit Airlines
San Juan — Orlando
3h 53m stop
18:05 — 20:15 NK1147 Spirit Airlines
Orlando — Chicago
10h 16m
including layover
Find flight
from$141
10:42 — 19:18
10:29 — 12:19 F92283 Frontier Airlines
San Juan — Miami
4h 36m stop
17:21 — 19:36 F92109 Frontier Airlines
Miami — Chicago
10h 36m
including layover
Find flight
from$90
11:16 — 19:13
13:55 — 16:59 F91015 Frontier Airlines
San Juan — Philadelphia
3h 39m stop
22:57 — 00:20 F94367 Frontier Airlines
Philadelphia — Chicago
9h 57m
including layover
Find flight
from$90
11:45 — 17:37
11:45 — 14:52 F92265 Frontier Airlines
San Juan — Baltimore
1h 41m stop
16:33 — 17:37 F93087 Frontier Airlines
Baltimore — Chicago
7h 52m
including layover
Find flight
from$112
12:45 — 00:59
+1 day
11:18 — 13:35 F93505 Frontier Airlines
San Juan — Orlando
7h 58m stop
09:56 — 12:05 F93043 Frontier Airlines
Orlando — Chicago
14h 14m
including layover
Find flight
from$89
13:54 — 22:41
13:54 — 17:05 F94249 Frontier Airlines
San Juan — Dallas
3h 14m stop
20:19 — 22:41 F92882 Frontier Airlines
Dallas — Chicago
10h 47m
including layover
Find flight
from$90
13:55 — 23:47
13:55 — 16:59 F91015 Frontier Airlines
San Juan — Philadelphia
5h 20m stop
22:19 — 23:47 F92111 Frontier Airlines
Philadelphia — Chicago
11h 52m
including layover
Find flight
from$90
14:00 — 21:55
14:00 — 16:56 F91225 Frontier Airlines
San Juan — Raleigh
3h 58m stop
20:54 — 21:55 F93717 Frontier Airlines
Raleigh — Chicago
9h 55m
including layover
Find flight
from$90
16:32 — 20:25
+1 day
16:32 — 18:44 F93979 Frontier Airlines
San Juan — Tampa
23h 56m stop
18:40 — 20:25 F93899 Frontier Airlines
Tampa — Chicago
29h 53m
including layover
Find flight
from$73
16:49 — 13:43
+1 day
16:49 — 19:14 F92215 Frontier Airlines
San Juan — Tampa
16h 29m stop
11:43 — 13:43 F91415 Frontier Airlines
Tampa — Chicago
22h 54m
including layover
Find flight
from$76
17:03 — 23:47
17:03 — 20:07 F94461 Frontier Airlines
San Juan — Philadelphia
2h 12m stop
22:19 — 23:47 F92111 Frontier Airlines
Philadelphia — Chicago
8h 44m
including layover
Find flight
from$90
17:03 — 00:20
+1 day
17:03 — 20:07 F94461 Frontier Airlines
San Juan — Philadelphia
2h 50m stop
22:57 — 00:20 F94367 Frontier Airlines
Philadelphia — Chicago
9h 17m
including layover
Find flight
from$90
18:14 — 10:06
+1 day
18:14 — 20:08 NK1637 Spirit Airlines
San Juan — Miami
11h 27m stop
07:35 — 10:06 NK396 Spirit Airlines
Miami — Chicago
17h 52m
including layover
Find flight
from$137
19:16 — 13:54
+1 day
11:18 — 13:35 F93505 Frontier Airlines
San Juan — Orlando
14h 17m stop
06:00 — 07:55 F91457 Frontier Airlines
Orlando — Chicago
20h 38m
including layover
Find flight
from$161
21:09 — 09:13
+1 day
21:49 — 00:10 F94725 Frontier Airlines
San Juan — Orlando
7h 50m stop
11:56 — 13:54 F91457 Frontier Airlines
Orlando — Chicago
14h 4m
including layover
Find flight
from$90
21:49 — 09:54
+1 day
21:49 — 00:10 F94725 Frontier Airlines
San Juan — Orlando
7h 20m stop
07:30 — 09:54 F93043 Frontier Airlines
Orlando — Chicago
14h 5m
including layover
Find flight
from$89
22:09 — 09:52
+1 day
22:09 — 23:58 NK1690 Spirit Airlines
San Juan — Miami
7h 32m stop
07:30 — 09:52 NK1986 Spirit Airlines
Miami — Chicago
13h 43m
including layover
Find flight
from$137
22:47 — 09:08
+1 day
22:47 — 01:38 F92081 Frontier Airlines
San Juan — Atlanta
6h 22m stop
08:00 — 09:08 F91441 Frontier Airlines
Atlanta — Chicago
12h 21m
including layover
Find flight
from$90
03:20 — 00:24
+1 day
03:20 — 06:26 NK838 Spirit Airlines
San Juan — Atlanta
11h 9m stop
17:35 — 18:56 NK967 Spirit Airlines
Atlanta — Houston
2h 51m stop
21:47 — 00:24 NK962 Spirit Airlines
Houston — Chicago
23h 4m
including layover
Find flight
from$177
04:39 — 20:48
04:39 — 07:47 NK3124 Spirit Airlines
San Juan — Baltimore
4h 42m stop
12:29 — 15:10 NK223 Spirit Airlines
Baltimore — Miami
3h 15m stop
18:25 — 20:48 NK7 Spirit Airlines
Miami — Chicago
18h 9m
including layover
Find flight
from$195
05:10 — 17:40
07:00 — 09:19 NK3164 Spirit Airlines
San Juan — Orlando
5h 4m stop
13:29 — 15:32 NK1096 Spirit Airlines
Orlando — Dallas
34m stop
17:58 — 20:26 NK241 Spirit Airlines
Dallas — Chicago
14h 30m
including layover
Find flight
from$208
07:00 — 22:55
07:00 — 10:36 NK1380 Spirit Airlines
San Juan — Dallas
2h 34m stop
13:10 — 17:31 NK1353 Spirit Airlines
Dallas — New York
3h 44m stop
21:15 — 22:55 NK225 Spirit Airlines
New York — Chicago
17h 55m
including layover
Find flight
from$215
12:27 — 22:51
12:27 — 14:46 NK1758 Spirit Airlines
San Juan — Orlando
3h 19m stop
18:05 — 19:19 NK359 Spirit Airlines
Orlando — Miami
1h 11m stop
20:30 — 22:51 NK718 Spirit Airlines
Miami — Chicago
12h 24m
including layover
Find flight
from$215
18:40 — 09:43
+1 day
18:40 — 20:33 NK1845 Spirit Airlines
San Juan — Miami
1h 55m stop
22:28 — 00:55 NK3175 Spirit Airlines
Miami — Dallas
6h 16m stop
07:11 — 09:43 NK3670 Spirit Airlines
Dallas — Chicago
17h 3m
including layover
Find flight
from$217
19:59 — 12:52
+1 day
19:59 — 21:50 NK1845 Spirit Airlines
San Juan — Miami
8h 6m stop
05:56 — 09:00 NK1897 Spirit Airlines
Miami — Newark
2h 14m stop
12:08 — 13:44 NK329 Spirit Airlines
Newark — Chicago
18h 53m
including layover
Find flight
from$151
20:31 — 21:07
+1 day
20:31 — 22:51 NK1647 Spirit Airlines
San Juan — New Orleans
11h 22m stop
10:13 — 13:08 NK2057 Spirit Airlines
New Orleans — Miami
5h 37m stop
18:45 — 21:07 NK7 Spirit Airlines
Miami — Chicago
26h 36m
including layover
Find flight
from$201
20:39 — 12:52
+1 day
20:39 — 22:25 NK262 Spirit Airlines
San Juan — Miami
7h 40m stop
06:05 — 09:00 NK385 Spirit Airlines
Miami — Newark
2h 13m stop
12:08 — 13:44 NK329 Spirit Airlines
Newark — Chicago
18h 13m
including layover
Find flight
from$200
*Departure and arrival times - local. Updated on April 4, 2025

Flight Information

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

Distance between San Juan and Chicago is 3314 miles. Time difference between the cities is 2h. Airplanes depart 02:05 to 22:47 from 2 San Juan airports and arrive 02:05 to 22:47 to 7 Chicago airports. Average flight time is 5h 19m.

  • The fastest flight 4h 59m
  • Average flight time 5h 19m
  • The earliest flight 02:05
  • The latest flight 22:47
  • Distance 2060 ml

The cheapest months to travel to Chicago are november (from 73 $), december (from 74 $), january (from 76 $).

The most expensive months are february (from 90 $), january (from 76 $), december (from 74 $).

What is the lowest airfare San Juan to Chicago?

The cheapest plane ticket found by our users is $73. This airfare is for economy class on one-way F93979 flight by Frontier Airlines for November 13, 2024 which leaves Luis Munoz Marin Intl in San Juan at 16:32 am and arrives at Chicago Midway at 20:25.

Economy class
$73
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Business class
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First class
?
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Popular Airlines on the Route

The flight San Juan — Chicago is served by 5 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Cape Air - 4 departures per week at the price of from $ 399 . And the most expensive tickets are offered by United Airlines airline - from $ 925.

Direct flights

There are 7 nonstop flights on the route. The fastest direct flight is NK492 by Spirit Airlines takes 4h 59m and the cheapest is F93979 by Frontier Airlines for $107.

  • UA - United Airlines
    from $270
    Find
  • NK - Spirit Airlines
    from $107
    Find
See more direct flights

Connecting Flights

There are 270 flights with layovers on the route. The fastest connecting flight is NK3160 by Spirit Airlines takes 7h 6m and the cheapest is F93979 by Frontier Airlines for $73.

  • 9K - Cape Air
    from $399
    Find
  • F9 - Frontier Airlines
    from $73
    Find
  • 3M - Gulfstream International Airlines
    from $416
    Find
  • UA - United Airlines
    from $276
    Find
  • NK - Spirit Airlines
    from $137
    Find
See more connecting flights

Airports

You can fly from San Juan to Chicago from 2 airports (Isla Grande, Luis Munoz Marin Intl).

San Juan airports

  • Isla Grande-SIG
    Find
  • Luis Munoz Marin Intl-SJU
    from $73
    Find

Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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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
    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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