background

Flight Deals from San Juan to Chicago O Hare Airport from $108

Fly where?

Top flight deals from leading airlines:

UA LogoB6 LogoQR LogoSQ LogoNH LogoEK LogoJL Logo

... and +100s more

Change Your Mind? No Problem

Cancel within 24 hours for a full refund—no questions asked.

Price Drop Protection

We’ll refund the difference if the price drops before you fly.

No Surprises at Checkout

The prices shown are exactly what you pay, with no hidden taxes or fees.

24/7 Support

Expert travel agents, ready to help anytime by phone, chat, or email.

Stops

  • Nonstop
    from $167
  • Up to 1 stop
    $220

Airlines

  • American Airlines
    $430
  • Frontier Airlines
    $286
  • JetBlue
    $342
  • Spirit Airlines
    $167
  • United Airlines
    $463

Cabin Class

  • Economy
    $167

Departure Airports

  • Luis Munoz Marin International Airport
    $167

Arrival Airports

  • Chicago Midway Airport
    $286
  • Chicago O Hare Airport
    $167

Layover Airports

  • General Edward Lawrence Logan International Airport
    $342
  • Hartsfield Jackson Atlanta International Airport
    $286
  • Miami International Airport
    $459
  • New York John F Kennedy Airport
    $342
  • Orlando International Airport
    $220
  • Washington Dulles Airport
    $468
Spirit Airlines Logo
7:43 pm – 11:57 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 14m
24 Oct
5h 14m
24 Oct
nonstop
Spirit Airlines Logo
9:06 pm – 2:51 am
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 45m
31 Oct
4h 45m
31 Oct
nonstop
$167
Spirit Airlines Logo
7:43 pm – 11:57 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 14m
24 Oct
5h 14m
24 Oct
nonstop
Spirit Airlines Logo
7:51 pm – 12:54 am
Chicago(ORD)San Juan(SJU)
ORD - SJU · 28h 3m
31 Oct
28h 3m
31 Oct
1 stop
MCO
$220
Spirit Airlines Logo
7:43 pm – 11:57 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 14m
24 Oct
5h 14m
24 Oct
nonstop
Spirit Airlines Logo
6:00 am – 2:12 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 7h 12m
31 Oct
7h 12m
31 Oct
1 stop
MCO
$235
Spirit Airlines Logo
7:43 pm – 11:57 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 14m
24 Oct
5h 14m
24 Oct
nonstop
Spirit Airlines Logo
7:51 pm – 2:12 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 17h 21m
31 Oct
17h 21m
31 Oct
1 stop
MCO
$238
Spirit Airlines Logo
7:43 pm – 11:57 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 14m
24 Oct
5h 14m
24 Oct
nonstop
Spirit Airlines Logo
6:00 am – 1:44 am
Chicago(ORD)San Juan(SJU)
ORD - SJU · 18h 44m
31 Oct
18h 44m
31 Oct
1 stop
MCO
$250
Spirit Airlines Logo
3:19 pm – 9:33 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 7h 14m
24 Oct
7h 14m
24 Oct
1 stop
MCO
Spirit Airlines Logo
9:06 pm – 2:51 am
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 45m
31 Oct
4h 45m
31 Oct
nonstop
$265
Frontier Airlines Logo
3:05 pm – 11:39 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 9h 34m
24 Oct
9h 34m
24 Oct
1 stop
ATL
Frontier Airlines Logo
9:32 am – 1:54 am
Chicago(MDW)San Juan(SJU)
MDW - SJU · 15h 22m
31 Oct
15h 22m
31 Oct
1 stop
MCO
$286
Frontier Airlines Logo
3:05 pm – 11:39 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 9h 34m
24 Oct
9h 34m
24 Oct
1 stop
ATL
Frontier Airlines Logo
9:32 am – 9:24 pm
Chicago(MDW)San Juan(SJU)
MDW - SJU · 10h 52m
31 Oct
10h 52m
31 Oct
1 stop
MCO
$286
Frontier Airlines Logo
3:05 pm – 11:39 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 9h 34m
24 Oct
9h 34m
24 Oct
1 stop
ATL
Frontier Airlines Logo
6:20 am – 2:19 pm
Chicago(MDW)San Juan(SJU)
MDW - SJU · 6h 59m
31 Oct
6h 59m
31 Oct
1 stop
ATL
$286
Frontier Airlines Logo
3:05 pm – 11:39 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 9h 34m
24 Oct
9h 34m
24 Oct
1 stop
ATL
Frontier Airlines Logo
5:11 am – 2:19 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 8h 8m
31 Oct
8h 8m
31 Oct
1 stop
ATL
$287
Frontier Airlines Logo
3:05 pm – 11:39 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 9h 34m
24 Oct
9h 34m
24 Oct
1 stop
ATL
Frontier Airlines Logo
5:25 am – 9:24 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 14h 59m
31 Oct
14h 59m
31 Oct
1 stop
MCO
$287
Frontier Airlines Logo
9:19 pm – 3:39 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 19h 20m
24 Oct
19h 20m
24 Oct
1 stop
MCO
Frontier Airlines Logo
6:20 am – 2:19 pm
Chicago(MDW)San Juan(SJU)
MDW - SJU · 6h 59m
31 Oct
6h 59m
31 Oct
1 stop
ATL
$295
Frontier Airlines Logo
9:19 pm – 3:39 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 19h 20m
24 Oct
19h 20m
24 Oct
1 stop
MCO
Frontier Airlines Logo
9:32 am – 1:54 am
Chicago(MDW)San Juan(SJU)
MDW - SJU · 15h 22m
31 Oct
15h 22m
31 Oct
1 stop
MCO
$295
JetBlue Logo
6:05 pm – 6:25 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 25h 20m
24 Oct
25h 20m
24 Oct
1 stop
JFK
JetBlue Logo
6:55 pm – 11:43 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 27h 48m
31 Oct
27h 48m
31 Oct
1 stop
BOS
$342
JetBlue Logo
2:25 pm – 6:25 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 29h
24 Oct
29h
24 Oct
1 stop
JFK
JetBlue Logo
6:55 pm – 11:43 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 27h 48m
31 Oct
27h 48m
31 Oct
1 stop
BOS
$342
JetBlue Logo
9:25 pm – 6:25 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 22h
24 Oct
22h
24 Oct
1 stop
JFK
JetBlue Logo
6:55 pm – 11:43 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 27h 48m
31 Oct
27h 48m
31 Oct
1 stop
BOS
$342
JetBlue Logo
8:22 pm – 9:22 am
San Juan(SJU)Chicago(ORD)
SJU - ORD · 14h
24 Oct
14h
24 Oct
1 stop
BOS
JetBlue Logo
6:55 pm – 11:43 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 27h 48m
31 Oct
27h 48m
31 Oct
1 stop
BOS
$352
JetBlue Logo
1:00 pm – 9:22 am
San Juan(SJU)Chicago(ORD)
SJU - ORD · 21h 22m
24 Oct
21h 22m
24 Oct
1 stop
BOS
JetBlue Logo
6:55 pm – 11:43 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 27h 48m
31 Oct
27h 48m
31 Oct
1 stop
BOS
$361
JetBlue Logo
9:25 pm – 6:25 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 22h
24 Oct
22h
24 Oct
1 stop
JFK
JetBlue Logo
6:55 pm – 11:11 am
Chicago(ORD)San Juan(SJU)
ORD - SJU · 15h 16m
31 Oct
15h 16m
31 Oct
1 stop
BOS
$366
JetBlue Logo
6:05 pm – 6:25 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 25h 20m
24 Oct
25h 20m
24 Oct
1 stop
JFK
JetBlue Logo
6:55 pm – 11:11 am
Chicago(ORD)San Juan(SJU)
ORD - SJU · 15h 16m
31 Oct
15h 16m
31 Oct
1 stop
BOS
$366
American Airlines Logo
3:00 pm – 7:20 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 20m
24 Oct
5h 20m
24 Oct
nonstop
American Airlines Logo
10:00 am – 3:40 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 40m
31 Oct
4h 40m
31 Oct
nonstop
$430
American Airlines Logo
3:00 pm – 7:20 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 20m
24 Oct
5h 20m
24 Oct
nonstop
American Airlines Logo
7:05 pm – 12:39 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 16h 34m
31 Oct
16h 34m
31 Oct
1 stop
MIA
$459
American Airlines Logo
7:00 pm – 8:53 am
San Juan(SJU)Chicago(ORD)
SJU - ORD · 14h 53m
24 Oct
14h 53m
24 Oct
1 stop
MIA
American Airlines Logo
10:00 am – 3:40 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 40m
31 Oct
4h 40m
31 Oct
nonstop
$459
United Airlines Logo
3:56 pm – 8:03 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 7m
24 Oct
5h 7m
24 Oct
nonstop
United Airlines Logo
2:20 pm – 8:00 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 40m
31 Oct
4h 40m
31 Oct
nonstop
$463
United Airlines Logo
3:56 pm – 8:03 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 7m
24 Oct
5h 7m
24 Oct
nonstop
United Airlines Logo
8:55 am – 2:40 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 45m
31 Oct
4h 45m
31 Oct
nonstop
$463
United Airlines Logo
4:55 pm – 11:15 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 7h 20m
24 Oct
7h 20m
24 Oct
1 stop
IAD
United Airlines Logo
2:20 pm – 8:00 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 40m
31 Oct
4h 40m
31 Oct
nonstop
$468
United Airlines Logo
4:55 pm – 11:15 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 7h 20m
24 Oct
7h 20m
24 Oct
1 stop
IAD
United Airlines Logo
8:55 am – 2:40 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 45m
31 Oct
4h 45m
31 Oct
nonstop
$468
American Airlines Logo
5:00 pm – 11:58 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 7h 58m
24 Oct
7h 58m
24 Oct
1 stop
MIA
American Airlines Logo
10:00 am – 3:40 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 40m
31 Oct
4h 40m
31 Oct
nonstop
$502
American Airlines Logo
7:00 pm – 11:03 am
San Juan(SJU)Chicago(ORD)
SJU - ORD · 17h 3m
24 Oct
17h 3m
24 Oct
1 stop
MIA
American Airlines Logo
10:00 am – 3:40 pm
Chicago(ORD)San Juan(SJU)
ORD - SJU · 4h 40m
31 Oct
4h 40m
31 Oct
nonstop
$502
American Airlines Logo
3:00 pm – 7:20 pm
San Juan(SJU)Chicago(ORD)
SJU - ORD · 5h 20m
24 Oct
5h 20m
24 Oct
nonstop
American Airlines Logo
7:05 pm – 11:06 am
Chicago(ORD)San Juan(SJU)
ORD - SJU · 15h 1m
31 Oct
15h 1m
31 Oct
1 stop
MIA
$502

Top Deals on flights from San Juan to Chicago O Hare Airport

San Juan, PR (SJU) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

Nov 13

SJU
3h 22m
Direct

Nov 13

ORD

as low as

$108

San Juan, PR (SJU) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

Dec 5

SJU
4h 54m
MCO

Dec 5

ORD

as low as

$138

San Juan, PR (SJU) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

Dec 8

SJU
7h 11m
FLL

Dec 8

ORD

as low as

$146

San Juan, PR (SJU) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Dec 18

SJU
8h 9m
ATL

Dec 19

ORD

as low as

$146

San Juan, PR (SJU) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Apr 18

SJU
7h 10m
JFK

Apr 18

ORD

as low as

$153

San Juan, PR (SJU) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

Jan 8

SJU
5h 30m
MIA

Jan 8

ORD

as low as

$166

San Juan, PR (SJU) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Feb 10

SJU
3h 22m
Direct

Feb 10

ORD

as low as

$172

San Juan, PR (SJU) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Jan 21

SJU
5h 49m
IAD

Jan 21

ORD

as low as

$176

San Juan, PR (SJU) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Feb 3

SJU
7h 12m
IAH

Feb 3

ORD

as low as

$176

San Juan, PR (SJU) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

Dec 5

SJU
17h 13m
FLL
DFW

Dec 6

ORD

as low as

$191

San Juan, PR (SJU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Dec 12

SJU
3h 31m
Direct

Dec 12

ORD

as low as

$193

San Juan, PR (SJU) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Dec 19

SJU
7h 25m
PHL

Dec 19

ORD

as low as

$197

Flights to Chicago