Take off on cheap flights from San Juan to Chicago, your adventure starts now!

Find cheap airline tickets from San Juan to Chicago by date

  • any
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • any
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • price
  • month of departure
  • month of return
$206
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$206
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$207
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$211
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$212
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$219
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$225
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$247
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$247
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$248
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$251
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$252
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$252
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$253
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$253
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$253
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 1, 2019
11:40p ORD » 2:56p SJU
Spirit Airlines 1 stop (15h16m)
$254
outward: May 2, 2019
12:40p SJU » 3:14a ORD
Spirit Airlines 1 stop (14h34m)
inbound: May 6, 2019
4:40p ORD » 3:13a SJU
Spirit Airlines 1 stop (10h33m)
$255
outward: Apr 30, 2019
8:19p SJU » 3:14p ORD
Spirit Airlines 1 stop (18h55m)
inbound: May 2, 2019
1:35a ORD » 7:45a SJU
Spirit Airlines 1 stop (6h10m)
$267
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 17, 2019
1:35a ORD » 7:45a SJU
Spirit Airlines 1 stop (6h10m)
$268
outward: May 1, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: May 2, 2019
1:35a ORD » 7:45a SJU
Spirit Airlines 1 stop (6h10m)
$269
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 16, 2019
11:40p ORD » 2:55p SJU
Spirit Airlines 1 stop (15h15m)
$269
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 16, 2019
11:40p ORD » 2:55p SJU
Spirit Airlines 1 stop (15h15m)
$269
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 17, 2019
12:51a ORD » 8:45a SJU
Spirit Airlines 1 stop (7h54m)
$269
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 16, 2019
11:40p ORD » 2:55p SJU
Spirit Airlines 1 stop (15h15m)
$270
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 16, 2019
11:40p ORD » 2:55p SJU
Spirit Airlines 1 stop (15h15m)
$270
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 16, 2019
11:40p ORD » 2:55p SJU
Spirit Airlines 1 stop (15h15m)
$270
outward: Apr 11, 2019
1:53a SJU » 6:19a ORD
Spirit Airlines 1 stop (28h26m)
inbound: Apr 17, 2019
12:51a ORD » 8:45a SJU
Spirit Airlines 1 stop (7h54m)
$270
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 16, 2019
11:40p ORD » 2:55p SJU
Spirit Airlines 1 stop (15h15m)
$270
outward: Apr 10, 2019
9:45a SJU » 4:42p ORD
Spirit Airlines 1 stop (6h57m)
inbound: Apr 16, 2019
11:40p ORD » 2:55p SJU
Spirit Airlines 1 stop (15h15m)
$271
outward: Apr 11, 2019
1:53a SJU » 9:24p ORD
Spirit Airlines 1 stop (19h31m)
inbound: Apr 17, 2019
12:51a ORD » 8:45a SJU
Spirit Airlines 1 stop (7h54m)
Return
Departure
12 April Apr Friday $retDate.dayShortName
13 April Apr Saturday $retDate.dayShortName
14 April Apr Sunday $retDate.dayShortName
15 April Apr Monday $retDate.dayShortName
16 April Apr Tuesday $retDate.dayShortName
17 April Apr Wednesday $retDate.dayShortName
18 April Apr Thursday $retDate.dayShortName
05 April Apr Friday $outDate.dayShortName
$324 $325
06 April Apr Saturday $outDate.dayShortName
$316 $300 $308
07 April Apr Sunday $outDate.dayShortName
$309
08 April Apr Monday $outDate.dayShortName
09 April Apr Tuesday $outDate.dayShortName
$305 $321
10 April Apr Wednesday $outDate.dayShortName
$273 $323 $264 $264
11 April Apr Thursday $outDate.dayShortName
$278 $264
Choose when you'd like to depart to Chicago (USA):
Find the cheapest San Juan Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for San Juan - Chicago with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from San Juan to Chicago

  • any
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • all
  • Air Canada
  • American Airlines
  • Delta Air Lines
  • Frontier Airlines
  • JetBlue
  • Spirit Airlines
  • United Airlines
JetBlue
outbound: May 12, 2019
JetBlue 1 stop
return: Jun 3, 2019
JetBlue 1 stop
Spirit Airlines
outbound: May 12, 2019
Spirit Airlines 1 stop
return: Jun 3, 2019
Spirit Airlines 1 stop
United Airlines
outbound: Aug 9, 2019
United Airlines 1 stop
return: Aug 16, 2019
United Airlines direct
Air Canada
outbound: Aug 9, 2019
Air Canada 1 stop
return: Aug 16, 2019
Air Canada direct
Frontier Airlines
outbound: Aug 11, 2019
Frontier Airlines 1 stop
return: Aug 19, 2019
United Airlines direct
American Airlines
outbound: Jul 13, 2019
American Airlines direct
return: Jul 21, 2019
American Airlines direct
Delta Air Lines
outbound: Jul 31, 2019
Delta Air Lines 1 stop
return: Aug 8, 2019
Delta Air Lines 1 stop

Travel tips for flights San Juan - Chicago

Average flight duration: 13h48m (flight with stopovers)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Mar 22, 2019 3:07 AM, GMT-5
  • Weather:
  • min. 35ºF, max. 42ºF
  • Departure city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • Mar 22, 2019 4:07 AM, GMT-4
  • Weather:
  • min. 65ºF, max. 84ºF