Flights from San Juan to Chicago from $40

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Flights Chicago → San Juan
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Airfare Deals San Juan to Chicago

On HolidayPrice.com you will find 4 direct and 6 connecting flights from San Juan to Chicago at a price of from $40. You can compare airfare deals from airlines and multiple travel sites, 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.

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The cost of airline tickets from San Juan to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

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Cheap flights from San Juan
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Airline tickets to United States

One way flight from San Juan to Chicago

Below are the prices of tickets for direct one-way flights from San Juan to Chicago. The cheapest flight from San Juan to Chicago starts from $40 – the departure date for this flight is 27 September 2023.

Sort by: Departure dateCheap flightsFast flightsDirect flights
25.10.2023 Wednesday
from $40
Economy Found yesterday
Nonstop 5 hours 6 min
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18.10.2023 Wednesday
from $59
Economy Found 2 days
Nonstop 5 hours 6 min
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14.10.2023 Saturday
from $59
Economy Found 2023-09-19
Nonstop 5 hours 6 min
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17.10.2023 Tuesday
from $60
Economy Found yesterday
Nonstop 5 hours 6 min
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19.10.2023 Thursday
from $60
Economy Found 2023-09-19
Nonstop 5 hours 6 min
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24.10.2023 Tuesday
from $73
Economy Found yesterday
1 Stopover 13 hours 34 min
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17.10.2023 Tuesday
from $75
Economy Found yesterday
1 Stopover 10 hours 29 min
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19.10.2023 Thursday
from $76
Economy Found 2023-09-19
1 Stopover 10 hours 34 min
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06.10.2023 Friday
from $83
Economy Found 2 days
Nonstop 5 hours 6 min
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05.10.2023 Thursday
from $83
Economy Found 2 days
1 Stopover 10 hours 34 min
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11.10.2023 Wednesday
from $83
Economy Found yesterday
1 Stopover 10 hours 34 min
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10.10.2023 Tuesday
from $83
Economy Found yesterday
1 Stopover 10 hours 29 min
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02.10.2023 Monday
from $83
Economy Found yesterday
Nonstop 4 hours 55 min
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04.10.2023 Wednesday
from $83 Aviakassa
Economy Found yesterday
1 Stopover 26 hours 45 min
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20.10.2023 Friday
from $84
Economy Found 2023-09-19
Nonstop 5 hours 6 min
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27.10.2023 Friday
from $85
Economy Found 2023-09-19
Nonstop 5 hours 6 min
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13.10.2023 Friday
from $87
Economy Found 2 days
1 Stopover 14 hours 18 min
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04.10.2023 Wednesday
from $92 City.Travel
Economy Found yesterday
Nonstop 4 hours 55 min
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16.10.2023 Monday
from $93
Economy Found 2023-09-19
1 Stopover 9 hours 30 min
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29.10.2023 Sunday
from $94
Economy Found yesterday
Nonstop 5 hours 6 min
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27.10.2023 Friday
from $101
Economy Found 2023-09-19
1 Stopover 10 hours 29 min
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23.10.2023 Monday
from $101
Economy Found yesterday
1 Stopover 17 hours 47 min
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26.10.2023 Thursday
from $121
Economy Found 2 days
1 Stopover 10 hours 34 min
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20.10.2023 Friday
from $122
Economy Found 2023-09-19
1 Stopover 14 hours 39 min
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15.10.2023 Sunday
from $122
Economy Found 2023-09-19
1 Stopover 7 hours 58 min
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01.10.2023 Sunday
from $131
Economy Found today
1 Stopover 9 hours 31 min
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16.10.2023 Monday
from $139
Economy Found 2023-09-19
Nonstop 5 hours 6 min
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06.10.2023 Friday
from $141
Economy Found 2 days
1 Stopover 17 hours 47 min
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04.10.2023 Wednesday
from $280 Aviakassa
Economy Found yesterday
2 Stopovers 13 hours 24 min
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04.10.2023 Wednesday
from $321 Aviakassa
Economy Found yesterday
3 Stopovers 44 hours 26 min
Find Flights
*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from San Juan to Chicago

You can buy a round-trip ticket from San Juan to Chicago (United States) and back using the table below. The best offer starts from $100, the flight dates are: there on 30 November 2023 year and back on 05 December 2023 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Frontier Airlines F9 3271 Morning flight
Departure 30.11.23 10:00, Th
Direct Trip 6 days
Return 05.12.23 23:58, Tu
Find Flights from $100
Frontier Airlines F9 2655 Evening flight
Departure 13.10.23 19:00, Fr
Direct Trip 8 days
Return 21.10.23 13:31, Sa
Find Flights from $103
Frontier Airlines F9 2655 Evening flight
Departure 27.10.23 19:00, Fr
Direct Trip 3 days
Return 30.10.23 13:31, Mo
Find Flights from $112
Frontier Airlines F9 3271 Morning flight
Departure 29.11.23 10:00, We
Direct Trip 8 days
Return 06.12.23 23:58, We
Find Flights from $112
Frontier Airlines F9 2655 Evening flight
Departure 27.09.23 19:04, We
Direct Trip 7 days
Return 04.10.23 23:14, We
Find Flights from $115
Frontier Airlines F9 3271 Morning flight
Departure 05.12.23 10:00, Tu
Direct Trip 8 days
Return 12.12.23 23:58, Tu
Find Flights from $115
Frontier Airlines F9 2655 Evening flight
Departure 21.10.23 19:00, Sa
Direct Trip 4 days
Return 25.10.23 13:31, We
Find Flights from $118
Frontier Airlines F9 2655 Evening flight
Departure 25.10.23 19:00, We
Direct Trip 3 days
Return 28.10.23 13:31, Sa
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 18.10.23 19:00, We
Direct Trip 12 days
Return 30.10.23 13:31, Mo
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 08.11.23 20:00, We
Direct Trip 3 days
Return 11.11.23 14:31, Sa
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 11.10.23 19:00, We
Direct Trip 14 days
Return 25.10.23 13:31, We
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 14.10.23 19:00, Sa
Direct Trip 9 days
Return 23.10.23 13:31, Mo
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 28.10.23 19:00, Sa
Direct Trip 2 days
Return 30.10.23 13:31, Mo
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 07.10.23 19:00, Sa
Direct Trip 11 days
Return 18.10.23 13:31, We
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 03.11.23 19:00, Fr
Direct Trip 3 days
Return 06.11.23 14:31, Mo
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 04.11.23 19:00, Sa
Direct Trip 7 days
Return 11.11.23 14:31, Sa
Find Flights from $119
Frontier Airlines F9 2655 Evening flight
Departure 29.09.23 19:04, Fr
Direct Trip 3 days
Return 03.10.23 00:14, Tu
Find Flights from $119
Spirit Airlines NK 130 Evening flight
Departure 01.11.23 18:22, We
Direct Trip 7 days
Return 08.11.23 13:40, We
Find Flights from $120
Spirit Airlines NK 130 Evening flight
Departure 19.10.23 18:22, Th
Direct Trip 4 days
Return 23.10.23 12:40, Mo
Find Flights from $120
Spirit Airlines NK 130 Evening flight
Departure 12.10.23 18:22, Th
Direct Trip 4 days
Return 16.10.23 12:40, Mo
Find Flights from $120
Spirit Airlines NK 130 Evening flight
Departure 02.11.23 18:22, Th
Direct Trip 4 days
Return 06.11.23 13:40, Mo
Find Flights from $121
Spirit Airlines NK 130 Evening flight
Departure 11.11.23 19:22, Sa
Direct Trip 3 days
Return 14.11.23 13:40, Tu
Find Flights from $121
Spirit Airlines NK 130 Evening flight
Departure 24.10.23 18:22, Tu
Direct Trip 7 days
Return 31.10.23 12:40, Tu
Find Flights from $121
Spirit Airlines NK 130 Evening flight
Departure 31.10.23 18:22, Tu
Direct Trip 14 days
Return 14.11.23 13:40, Tu
Find Flights from $121
Spirit Airlines NK 130 Evening flight
Departure 17.10.23 18:22, Tu
Direct Trip 7 days
Return 24.10.23 12:40, Tu
Find Flights from $121
Spirit Airlines NK 130 Evening flight
Departure 10.10.23 18:22, Tu
Direct Trip 14 days
Return 24.10.23 12:40, Tu
Find Flights from $121
Spirit Airlines NK 130 Evening flight
Departure 07.11.23 19:22, Tu
Direct Trip 4 days
Return 11.11.23 13:40, Sa
Find Flights from $121
Frontier Airlines F9 2655 Evening flight
Departure 25.09.23 19:04, Mo
Direct Trip 2 days
Return 27.09.23 23:14, We
Find Flights from $124
Frontier Airlines F9 2655 Evening flight
Departure 22.09.23 19:04, Fr
Direct Trip 5 days
Return 27.09.23 23:14, We
Find Flights from $124
Frontier Airlines F9 3271 Morning flight
Departure 01.12.23 10:00, Fr
Direct Trip 5 days
Return 05.12.23 23:58, Tu
Find Flights from $124
Frontier Airlines F9 2655 Evening flight
Departure 23.09.23 19:22, Sa
Direct Trip 4 days
Return 27.09.23 23:14, We
Find Flights from $130
Frontier Airlines F9 2655 Evening flight
Departure 04.10.23 19:04, We
Direct Trip 3 days
Return 07.10.23 13:31, Sa
Find Flights from $134
Frontier Airlines F9 3271 Morning flight
Departure 03.12.23 10:00, Su
Direct Trip 3 days
Return 05.12.23 23:58, Tu
Find Flights from $142
Frontier Airlines F9 2655 Evening flight
Departure 06.10.23 19:00, Fr
Direct Trip 5 days
Return 11.10.23 13:31, We
Find Flights from $142
Frontier Airlines F9 2655 Evening flight
Departure 10.11.23 20:00, Fr
Direct Trip 3 days
Return 13.11.23 14:31, Mo
Find Flights from $142
Frontier Airlines F9 3271 Morning flight
Departure 06.12.23 10:00, We
Direct Trip 4 days
Return 09.12.23 23:58, Sa
Find Flights from $143
Frontier Airlines F9 2655 Evening flight
Departure 20.10.23 19:00, Fr
Direct Trip 3 days
Return 23.10.23 13:31, Mo
Find Flights from $143
Spirit Airlines NK 3147 Evening flight
Departure 02.12.23 17:47, Sa
1 Stopover Trip 3 days
Return 05.12.23 13:30, Tu
Find Flights from $144
Spirit Airlines NK 130 Evening flight
Departure 09.11.23 19:22, Th
Direct Trip 4 days
Return 13.11.23 13:40, Mo
Find Flights from $144
Spirit Airlines NK 130 Evening flight
Departure 21.11.23 19:28, Tu
Direct Trip 14 days
Return 05.12.23 13:30, Tu
Find Flights from $144
Spirit Airlines NK 3147 Day flight
Departure 03.10.23 14:38, Tu
1 Stopover Trip 7 days
Return 10.10.23 12:40, Tu
Find Flights from $144
Spirit Airlines NK 3147 Day flight
Departure 05.10.23 16:39, Th
1 Stopover Trip 5 days
Return 10.10.23 12:40, Tu
Find Flights from $144
Spirit Airlines NK 130 Evening flight
Departure 26.10.23 18:22, Th
Direct Trip 4 days
Return 30.10.23 12:40, Mo
Find Flights from $145
Frontier Airlines F9 2655 Evening flight
Departure 02.10.23 19:04, Mo
Direct Trip 16 days
Return 18.10.23 13:31, We
Find Flights from $149
Spirit Airlines NK 2893 Morning flight
Departure 16.10.23 05:08, Mo
1 Stopover Trip 7 days
Return 23.10.23 12:40, Mo
Find Flights from $152
Spirit Airlines NK 2893 Morning flight
Departure 30.10.23 05:08, Mo
1 Stopover Trip 7 days
Return 06.11.23 13:40, Mo
Find Flights from $153
Spirit Airlines NK 130 Evening flight
Departure 28.09.23 18:11, Th
Direct Trip 4 days
Return 02.10.23 12:20, Mo
Find Flights from $155
Frontier Airlines F9 3271 Morning flight
Departure 23.11.23 10:00, Th
Direct Trip 18 days
Return 10.12.23 23:58, Su
Find Flights from $155
Spirit Airlines NK 3147 Evening flight
Departure 15.11.23 17:47, We
1 Stopover Trip 17 days
Return 02.12.23 13:30, Sa
Find Flights from $160
Frontier Airlines F9 3271 Morning flight
Departure 04.12.23 10:00, Mo
Direct Trip 8 days
Return 11.12.23 23:58, Mo
Find Flights from $163
Frontier Airlines F9 2655 Evening flight
Departure 30.09.23 19:22, Sa
Direct Trip 4 days
Return 04.10.23 23:14, We
Find Flights from $167
Frontier Airlines F9 3271 Morning flight
Departure 16.11.23 10:00, Th
Direct Trip 17 days
Return 02.12.23 23:58, Sa
Find Flights from $168
Frontier Airlines F9 3271 Day flight
Departure 20.12.23 12:25, We
Direct Trip 21 day
Return 10.01.24 23:58, We
Find Flights from $168
Frontier Airlines F9 2655 Evening flight
Departure 06.11.23 20:00, Mo
Direct Trip 4 days
Return 10.11.23 14:31, Fr
Find Flights from $169
Spirit Airlines NK 130 Evening flight
Departure 29.10.23 18:22, Su
Direct Trip 14 days
Return 12.11.23 13:40, Su
Find Flights from $169
Frontier Airlines F9 3271 Morning flight
Departure 08.12.23 10:00, Fr
Direct Trip 4 days
Return 11.12.23 23:58, Mo
Find Flights from $175
Frontier Airlines F9 3271 Morning flight
Departure 22.11.23 10:00, We
Direct Trip 19 days
Return 10.12.23 23:58, Su
Find Flights from $176
Spirit Airlines NK 130 Evening flight
Departure 13.11.23 19:22, Mo
1 Stopover Trip 2 days
Return 16.11.23 00:51, Th
Find Flights from $177
Frontier Airlines F9 3271 Day flight
Departure 15.12.23 12:25, Fr
Direct Trip 27 days
Return 11.01.24 23:35, Th
Find Flights from $178
Frontier Airlines F9 2669 Morning flight
Departure 15.10.23 07:31, Su
1 Stopover Trip 6 days
Return 21.10.23 13:31, Sa
Find Flights from $182
Frontier Airlines F9 2669 Morning flight
Departure 22.10.23 07:31, Su
1 Stopover Trip 3 days
Return 25.10.23 13:31, We
Find Flights from $182
Frontier Airlines F9 2667 Morning flight
Departure 26.09.23 07:32, Tu
1 Stopover Trip 7 days
Return 03.10.23 00:14, Tu
Find Flights from $182
Spirit Airlines NK 130 Evening flight
Departure 12.11.23 19:22, Su
1 Stopover Trip 3 days
Return 16.11.23 00:51, Th
Find Flights from $186
Frontier Airlines F9 3271 Morning flight
Departure 17.11.23 10:00, Fr
Direct Trip 15 days
Return 01.12.23 23:58, Fr
Find Flights from $187
Frontier Airlines F9 3271 Morning flight
Departure 19.11.23 10:00, Su
Direct Trip 12 days
Return 30.11.23 23:58, Th
Find Flights from $188
Frontier Airlines F9 3271 Morning flight
Departure 20.11.23 10:00, Mo
Direct Trip 15 days
Return 04.12.23 23:58, Mo
Find Flights from $194
Spirit Airlines NK 2893 Morning flight
Departure 23.10.23 05:08, Mo
1 Stopover Trip 7 days
Return 30.10.23 12:40, Mo
Find Flights from $195
Spirit Airlines NK 883 Morning flight
Departure 08.10.23 09:25, Su
1 Stopover Trip 9 days
Return 17.10.23 12:40, Tu
Find Flights from $197
Spirit Airlines NK 130 Evening flight
Departure 24.09.23 18:11, Su
Direct Trip 14 days
Return 08.10.23 12:40, Su
Find Flights from $199
Frontier Airlines F9 3271 Day flight
Departure 25.12.23 12:25, Mo
Direct Trip 15 days
Return 09.01.24 23:58, Tu
Find Flights from $199
Spirit Airlines NK 130 Evening flight
Departure 18.11.23 19:28, Sa
Direct Trip 14 days
Return 02.12.23 13:30, Sa
Find Flights from $199
Spirit Airlines NK 130 Evening flight
Departure 14.11.23 19:22, Tu
Direct Trip 14 days
Return 28.11.23 13:30, Tu
Find Flights from $205
Spirit Airlines NK 883 Morning flight
Departure 28.11.23 09:30, Tu
1 Stopover Trip 7 days
Return 05.12.23 13:30, Tu
Find Flights from $205
Spirit Airlines NK 2893 Morning flight
Departure 09.10.23 05:08, Mo
1 Stopover Trip 1 day
Return 10.10.23 12:40, Tu
Find Flights from $206
Frontier Airlines F9 3271 Morning flight
Departure 11.12.23 10:00, Mo
Direct Trip 4 days
Return 14.12.23 23:58, Th
Find Flights from $207
Frontier Airlines F9 3271 Day flight
Departure 24.12.23 12:25, Su
Direct Trip 16 days
Return 09.01.24 23:58, Tu
Find Flights from $217
Spirit Airlines NK 883 Morning flight
Departure 05.11.23 10:25, Su
1 Stopover Trip 7 days
Return 12.11.23 13:40, Su
Find Flights from $221
Frontier Airlines F9 2673 Morning flight
Departure 21.09.23 06:58, Th
1 Stopover Trip 3 days
Return 24.09.23 00:14, Su
Find Flights from $225
Frontier Airlines F9 3271 Morning flight
Departure 07.12.23 10:00, Th
Direct Trip 8 days
Return 14.12.23 23:58, Th
Find Flights from $228
Frontier Airlines F9 3271 Day flight
Departure 16.12.23 12:25, Sa
Direct Trip 19 days
Return 04.01.24 00:31, Th
Find Flights from $232
Frontier Airlines F9 3271 Morning flight
Departure 13.12.23 10:00, We
Direct Trip 22 days
Return 04.01.24 00:31, Th
Find Flights from $232
Frontier Airlines F9 3271 Morning flight
Departure 12.12.23 10:00, Tu
Direct Trip 23 days
Return 04.01.24 00:31, Th
Find Flights from $232
Frontier Airlines F9 3271 Morning flight
Departure 25.11.23 10:00, Sa
Direct Trip 1 day
Return 25.11.23 23:58, Sa
Find Flights from $242
Frontier Airlines F9 2665 Night flight
Departure 02.10.23 00:52, Mo
1 Stopover Trip 2 days
Return 03.10.23 18:19, Tu
Find Flights from $244
Frontier Airlines F9 3271 Day flight
Departure 22.12.23 12:25, Fr
Direct Trip 17 days
Return 08.01.24 23:58, Mo
Find Flights from $245
Frontier Airlines F9 3271 Day flight
Departure 26.12.23 12:25, Tu
Direct Trip 15 days
Return 10.01.24 23:58, We
Find Flights from $257
Spirit Airlines NK 796 Morning flight
Departure 24.11.23 08:45, Fr
1 Stopover Trip 7 days
Return 01.12.23 13:30, Fr
Find Flights from $258
Frontier Airlines F9 3271 Day flight
Departure 27.12.23 12:25, We
Direct Trip 14 days
Return 10.01.24 23:58, We
Find Flights from $263
Frontier Airlines F9 3271 Day flight
Departure 18.12.23 12:25, Mo
Direct Trip 15 days
Return 02.01.24 00:31, Tu
Find Flights from $270
Frontier Airlines F9 3271 Day flight
Departure 17.12.23 12:25, Su
Direct Trip 18 days
Return 04.01.24 00:31, Th
Find Flights from $270
Frontier Airlines F9 3271 Day flight
Departure 19.12.23 12:25, Tu
Direct Trip 16 days
Return 04.01.24 00:31, Th
Find Flights from $270
Spirit Airlines NK 796 Morning flight
Departure 27.11.23 08:45, Mo
1 Stopover Trip 4 days
Return 01.12.23 00:51, Fr
Find Flights from $287
Frontier Airlines F9 3271 Day flight
Departure 23.12.23 12:25, Sa
Direct Trip 13 days
Return 05.01.24 23:58, Fr
Find Flights from $290
Frontier Airlines F9 3271 Day flight
Departure 28.12.23 12:25, Th
Direct Trip 14 days
Return 11.01.24 23:35, Th
Find Flights from $291
Frontier Airlines F9 3271 Day flight
Departure 21.12.23 12:25, Th
Direct Trip 17 days
Return 07.01.24 23:58, Su
Find Flights from $298
Frontier Airlines F9 3271 Day flight
Departure 29.12.23 12:25, Fr
Direct Trip 6 days
Return 04.01.24 23:58, Th
Find Flights from $307
Frontier Airlines F9 3271 Morning flight
Departure 14.12.23 10:00, Th
Direct Trip 4 days
Return 18.12.23 00:31, Mo
Find Flights from $308
Spirit Airlines NK 2009 Evening flight
Departure 09.12.23 19:44, Sa
1 Stopover Trip 3 days
Return 12.12.23 23:10, Tu
Find Flights from $311
Frontier Airlines F9 3271 Morning flight
Departure 10.12.23 10:00, Su
Direct Trip 8 days
Return 18.12.23 00:31, Mo
Find Flights from $326
Spirit Airlines NK 796 Morning flight
Departure 26.11.23 08:45, Su
1 Stopover Trip 7 days
Return 03.12.23 13:30, Su
Find Flights from $418
*Prices include: baggage, hand luggage, airline fees and charges.
Not found promotions and sales.

Flight Schedule San Juan to Chicago 2023

The current flight schedule for the route from San Juan to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 4 flights every day, from 4hours 55min. Local departure and arrival times are indicated.
06:45 → 10:51
Frontier Airlines F92655 Frontier Airlines F92655
SJU → MDW
- Tu - Th - - Su
Check price
08:10 → 13:35
Southwest Airlines WN2775 Southwest Airlines WN2775
SJU → MDW
Mo - - Th Fr - -
Check price
10:55 → 19:35
Southwest Airlines WN1504 Southwest Airlines WN1504
SJU → MDW
Mo - - Th Fr - -
Check price
13:35 → 21:00
Southwest Airlines WN1962 Southwest Airlines WN1962
SJU → MDW
Mo - - - - - -
Check price
14:11 → 18:17
Spirit Airlines NK130 Spirit Airlines NK130
SJU → ORD
Mo - - Th Fr - Su
Check price
14:15 → 18:25
Spirit Airlines NK130 Spirit Airlines NK130
SJU → ORD
Mo Tu We Th Fr Sa Su
Check price
14:20 → 18:30
United Airlines UA2088 United Airlines UA2088
SJU → ORD
Mo Tu We Th Fr Sa Su
Check price
14:20 → 18:23
United Airlines UA2088 United Airlines UA2088
SJU → ORD
- - - - - Sa Su
Check price
15:04 → 18:59
Frontier Airlines F92655 Frontier Airlines F92655
SJU → MDW
Mo - We - Fr - -
Check price
15:22 → 19:17
Frontier Airlines F92655 Frontier Airlines F92655
SJU → MDW
- - - - - Sa -
Check price
15:41 → 19:44
United Airlines UA2088 United Airlines UA2088
SJU → ORD
Mo Tu We Th Fr - -
Check price

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from San Juan takes 04:56 minutes (excluding transfers). The distance between San Juan and Chicago is 2049 miles (3299 kilometers). Planes depart from San Juan between 00:04 and 22:55. The fastest flight from the company Southwest Airlines with flight number WN 3197. Flies for just 04:50 minutes with departure from Luis Munoz Marin and arrival in Chicago Midway.

time

Average flight time

04:56 min

distance

Distance

2049 mi

The earliest flight

The earliest flight

00:04

The latest flight

The latest flight

22:55

Airplane

The fastest flight

04:50

Airlines

Direct flight

There are 4 airlines that fly directly from San Juan to Chicago. The most popular company carrying out non-stop flights is United Airlines.

*Flight number

Flights with Transfers

Flights with transfers from San Juan to Chicago can be bought from 6 airlines:

  • JetBlue Airways: Orlando, West Palm Beach, New York
  • Frontier Airlines: Philadelphia, New York
  • Southwest Airlines: Orlando, West Palm Beach
  • Delta Air Lines: Atlanta
  • Spirit Airlines: Tampa, Philadelphia
  • American Airlines: West Palm Beach

*Transit cities

Airports

Airports serving the air communication between San Juan and Chicago. You can fly to Chicago from 1 San Juan airports. Planes arrive at 2 airport in Chicago.

San Juan airports:

Luis Munoz Marin  ~ 12 km* from $ 33

Chicago airports:

O'Hare  ~ 25 km* from $ 66Chicago Midway  ~ 14 km* from $ 101

*Distance from the airport to the city center

Aircraft

You can fly from San Juan to Chicago on board of 4 airlines that utilize 4 aircraft models.

  • Airbus A320
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900

Connecting cities

The list of cities on transfer flights to Chicago from San Juan. The best options are to fly through: Orlando, Philadelphia, New York, West Palm Beach, Atlanta, Baltimore, Tampa, Boston.

Orlando
Philadelphia
New York
West Palm Beach
Atlanta
Baltimore
Tampa
Boston

Cheap airline tickets from San Juan to United States

Here is a list of flights from San Juan to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

San Juan - New York DL 332 Delta Air Lines Boeing 757-200
00:25 Luis Munoz Marin
in a way 3 hours 35 min Direct
04:00 John F. Kennedy
Flights
from $263 05 January 2024
San Juan - Los Angeles UA 668 United Airlines Boeing 737-900
23:45 Luis Munoz Marin
in a way 8 hours 53 min Direct
08:38 Los Angeles
Flights
from $104 30 October 2023
San Juan - Miami B6 754 JetBlue Airways Airbus A320
10:46 Luis Munoz Marin
in a way 2 hours 14 min Direct
13:00 Fort Lauderdale Executive Airport
Flights
from $49 02 November 2023
San Juan - Chicago WN 3197 Southwest Airlines Boeing 737-800
19:40 Luis Munoz Marin
in a way 4 hours 50 min Direct
00:30 Chicago Midway
Flights
from $40 27 September 2023
San Juan - San Francisco WN 5614 Southwest Airlines Boeing 737-800
12:30 Luis Munoz Marin
in a way 9 hours 15 min Direct
21:45 Norman Y. Mineta San Jose
Flights
from $123 29 September 2023

All flights from San Juan

Flights from Puerto Rico to Chicago

Here are the cheapest flight bookings from Puerto Rico to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

San Juan - Chicago WN 3197 Southwest Airlines Boeing 737-800
19:40 Luis Munoz Marin
in a way 4 hours 50 min Direct
00:30 Chicago Midway
Flights
from $40 27 September 2023
Ponce - Chicago B6 668 JetBlue Airways Airbus A320
06:43 Mercedita Airport
in a way 7 hours 42 min 1 Stopover
14:25 Chicago Midway
Flights
from $124 21 October 2023
Aguadilla - Chicago UA 1162 United Airlines Boeing 737-900
08:50 Rafael Hernandez Airport
in a way 7 hours 24 min Direct
16:14 O'Hare
Flights
from $82 30 October 2023
Mayaguez - Chicago 9K 32 Cape Air Cessna Light Aircraft
15:42 Eugenio M. De Hostos Airport
in a way 9 hours 4 min 1 Stopover
00:46 O'Hare
Flights
from $158 11 October 2023

All flights to Chicago

Tips for buying a ticket

San Juan – Chicago – San Juan round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from San Juan to Chicago
Chicago city

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