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

Find cheap airline tickets from Chicago to San Juan by date

  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • price
  • month of departure
  • month of return
$157
outward: May 31, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$159
outward: Jun 1, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 4, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$164
outward: May 30, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$165
outward: Jun 1, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$166
outward: May 31, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$167
outward: May 31, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$168
outward: May 31, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$168
outward: Jun 1, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 4, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$169
outward: Jun 1, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 4, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$180
outward: May 30, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$180
outward: May 30, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$183
outward: May 30, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$194
outward: Jun 6, 2018
1:15a ORD » 8:29a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 19, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$207
outward: May 30, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$207
outward: May 30, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$208
outward: May 31, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$209
outward: Jun 6, 2018
1:15a ORD » 8:29a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 19, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$213
outward: Jun 7, 2018
1:15a ORD » 8:29a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 20, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$214
outward: May 31, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$216
outward: May 28, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 10, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$216
outward: Jun 1, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 4, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$217
outward: Jun 1, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 4, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$225
outward: May 31, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 6, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$228
outward: Jun 1, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jul 12, 2018
8:39a SJU » 5:11p ORD
Frontier Airlines 1 stop (8h32m)
$232
outward: Jun 6, 2018
1:15a ORD » 8:29a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 19, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$232
outward: May 30, 2018
1:45a ORD » 8:59a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 7, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$234
outward: Jun 6, 2018
1:15a ORD » 8:29a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 19, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$236
outward: Jun 6, 2018
1:15a ORD » 8:29a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 19, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$243
outward: Jun 13, 2018
1:15a ORD » 8:29a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 27, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
$247
outward: Jun 6, 2018
1:15a ORD » 8:29a SJU
Frontier Airlines 1 stop (7h14m)
inbound: Jun 19, 2018
8:39a SJU » 5:05p ORD
Frontier Airlines 1 stop (8h26m)
Return
Departure
05 June Jun Tuesday $retDate.dayShortName
06 June Jun Wednesday $retDate.dayShortName
07 June Jun Thursday $retDate.dayShortName
08 June Jun Friday $retDate.dayShortName
09 June Jun Saturday $retDate.dayShortName
10 June Jun Sunday $retDate.dayShortName
11 June Jun Monday $retDate.dayShortName
28 May May Monday $outDate.dayShortName
$293 $287 $287 $215 $346
29 May May Tuesday $outDate.dayShortName
$308 $282 $284 $361 $361
30 May May Wednesday $outDate.dayShortName
$321 $163 $232 $294
31 May May Thursday $outDate.dayShortName
$323 $156 $300
01 June Jun Friday $outDate.dayShortName
$164
02 June Jun Saturday $outDate.dayShortName
03 June Jun Sunday $outDate.dayShortName
$360 $360 $325
Choose when you'd like to depart to San Juan (Puerto Rico):
Find the cheapest Chicago San Juan flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - San Juan with these new dates, click on an offer. Want to depart from another city? Choose: New York - San Juan London - San Juan Miami - San Juan See more routes

Airlines operating flights from Chicago to San Juan

  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • all
  • American Airlines
  • Delta Air Lines
  • Frontier Airlines
  • United Airlines
Frontier Airlines
outbound: May 31, 2018
Frontier Airlines 1 stop
return: Jun 6, 2018
Frontier Airlines 1 stop
United Airlines
outbound: Jul 13, 2018
United Airlines direct
return: Jul 15, 2018
United Airlines 1 stop
American Airlines
outbound: May 31, 2018
American Airlines direct
return: Jun 6, 2018
American Airlines direct
Delta Air Lines
outbound: Jul 28, 2018
Delta Air Lines 1 stop
return: Aug 5, 2018
Delta Air Lines 1 stop

Travel tips for flights Chicago - San Juan

Information on San Juan
Route

Average flight duration: 7h50m (direct flight)

  • Arrival city:
  • San Juan, Puerto Rico
  • Airport(s):
  • Fernando Luis Ribas Dominicci Airport (SIG)
  • Luis Muñoz Marín International Airport (SJU)
  • Local time:
  • May 26, 2018 11:15 PM, GMT-4
  • Weather:
  • min. 58ºF, max. 73ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 26, 2018 10:15 PM, GMT-5
  • Weather:
  • min. 65ºF, max. 84ºF

Why travel by plane from Chicago to San Juan?

When traveling from Chicago to San Juan, travelers are able to take advantage of daily non-stop flights between the two cities, operated by a number of airlines including regular and low-cost operators. These include American Airlines, Southwest Airlines and United Airlines, which operate direct flights to San Juan with a flight time of around 4h 40m. Connecting flights are also available with a flight time of upwards of 6h. Departing from either O'Hare International Airport or Chicago Midway International Airport, flights touch down in San Juan's Luis Muñoz Marín International Airport.

What is there to see and do in San Juan?

The Puerto Rican capital city of San Juan is home to a host of activities and sights for visitors to enjoy. As well as the must-visit area of Old San Juan, filled with colorful houses and interesting attractions, there's also the opportunity to learn more about Bacardi rum at the Casa Bacardi factory and museum. Other museums to visit include the Museo de las Americas, the Museum of the Sea, and the Museum of Art Puerto Rico. After a day of exploring, relax in one of San Juan's restaurants or bars – the city boasts a lively nightlife scene!