24/7 Support
(855-706-2925)
Flight Deals from San Juan to Chicago from $108
Top flight deals from leading airlines:
... 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
- Nonstopfrom $167
- Up to 1 stop$220
Airlines
- American Airlines$430
- Frontier Airlines$285
- 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$285
- Chicago O Hare Airport$167
Layover Airports
- General Edward Lawrence Logan International Airport$342
- Hartsfield Jackson Atlanta International Airport$285
- Miami International Airport$459
- New York John F Kennedy Airport$342
- Orlando International Airport$220
- Philadelphia International Airport$285
- Washington Dulles Airport$468
7:43 pm – 11:57 pm
nonstop
9:06 pm – 2:51 am
nonstop
$167
7:43 pm – 11:57 pm
nonstop
7:51 pm – 12:54 am
1 stop
MCO$220
7:43 pm – 11:57 pm
nonstop
6:00 am – 2:12 pm
1 stop
MCO$235
7:43 pm – 11:57 pm
nonstop
7:51 pm – 2:12 pm
1 stop
MCO$238
7:43 pm – 11:57 pm
nonstop
6:00 am – 1:44 am
1 stop
MCO$250
3:19 pm – 9:33 pm
1 stop
MCO9:06 pm – 2:51 am
nonstop
$265
12:02 pm – 11:03 pm
1 stop
PHL9:32 am – 9:24 pm
1 stop
MCO$285
12:02 pm – 11:03 pm
1 stop
PHL6:20 am – 2:19 pm
1 stop
ATL$285
12:02 pm – 11:03 pm
1 stop
PHL9:32 am – 1:54 am
1 stop
MCO$285
9:19 pm – 10:21 am
1 stop
MCO6:20 am – 2:19 pm
1 stop
ATL$285
3:05 pm – 11:46 pm
1 stop
ATL6:20 am – 2:19 pm
1 stop
ATL$285
3:05 pm – 11:46 pm
1 stop
ATL9:32 am – 9:24 pm
1 stop
MCO$285
3:05 pm – 11:46 pm
1 stop
ATL9:32 am – 1:54 am
1 stop
MCO$285
12:02 pm – 11:03 pm
1 stop
PHL5:25 am – 9:24 pm
1 stop
MCO$286
12:02 pm – 11:03 pm
1 stop
PHL5:11 am – 2:19 pm
1 stop
ATL$286
2:25 pm – 6:25 pm
1 stop
JFK6:55 pm – 11:43 pm
1 stop
BOS$342
9:25 pm – 6:25 pm
1 stop
JFK6:55 pm – 11:43 pm
1 stop
BOS$342
6:05 pm – 6:25 pm
1 stop
JFK6:55 pm – 11:43 pm
1 stop
BOS$342
8:22 pm – 9:22 am
1 stop
BOS6:55 pm – 11:43 pm
1 stop
BOS$352
1:00 pm – 9:22 am
1 stop
BOS6:55 pm – 11:43 pm
1 stop
BOS$361
9:25 pm – 6:25 pm
1 stop
JFK6:55 pm – 11:11 am
1 stop
BOS$366
2:25 pm – 6:25 pm
1 stop
JFK6:55 pm – 11:11 am
1 stop
BOS$366
3:00 pm – 7:20 pm
nonstop
10:00 am – 3:40 pm
nonstop
$430
3:00 pm – 7:20 pm
nonstop
7:05 pm – 12:39 pm
1 stop
MIA$459
7:00 pm – 8:53 am
1 stop
MIA10:00 am – 3:40 pm
nonstop
$459
3:56 pm – 8:03 pm
nonstop
2:20 pm – 8:00 pm
nonstop
$463
3:56 pm – 8:03 pm
nonstop
8:55 am – 2:40 pm
nonstop
$463
4:55 pm – 11:15 pm
1 stop
IAD8:55 am – 2:40 pm
nonstop
$468
4:55 pm – 11:15 pm
1 stop
IAD2:20 pm – 8:00 pm
nonstop
$468
5:00 pm – 11:58 pm
1 stop
MIA10:00 am – 3:40 pm
nonstop
$502
Top Deals on flights from San Juan to Chicago
San Juan, PR (SJU) - Chicago, US (CHI)
Nov 7
SJU
3h 22m
Direct
Nov 7
ORD
as low as
$108
San Juan, PR (SJU) - Chicago, US (CHI)
Dec 5
SJU
6h 7m
MCO
Dec 5
ORD
as low as
$138
San Juan, PR (SJU) - Chicago, US (CHI)
Nov 16
SJU
5h 19m
PHL
Nov 16
MDW
as low as
$142
San Juan, PR (SJU) - Chicago, US (CHI)
Nov 15
SJU
6h 27m
MCO
Nov 15
MDW
as low as
$142
San Juan, PR (SJU) - Chicago, US (CHI)
Nov 13
SJU
5h 32m
ATL
Nov 13
MDW
as low as
$142
San Juan, PR (SJU) - Chicago, US (CHI)
Dec 8
SJU
7h 11m
FLL
Dec 8
ORD
as low as
$146
San Juan, PR (SJU) - Chicago, US (CHI)
Dec 12
SJU
6h 34m
TPA
Dec 12
MDW
as low as
$146
San Juan, PR (SJU) - Chicago, US (CHI)
Apr 18
SJU
7h 10m
JFK
Apr 18
ORD
as low as
$153
San Juan, PR (SJU) - Chicago, US (CHI)
Jan 8
SJU
5h 30m
MIA
Jan 8
ORD
as low as
$166
San Juan, PR (SJU) - Chicago, US (CHI)
Jan 21
SJU
3h 22m
Direct
Jan 21
ORD
as low as
$172
San Juan, PR (SJU) - Chicago, US (CHI)
Feb 3
SJU
5h 58m
EWR
Feb 3
ORD
as low as
$176
San Juan, PR (SJU) - Chicago, US (CHI)
Feb 9
SJU
5h 49m
IAD
Feb 9
ORD
as low as
$176
Frequently Asked Questions
Cheapest and fastest flight from San Juan to Chicago?
The cheapest flight is with Spirit Airlines at $167, 5h 14m. The fastest flight is with United Airlines at $463, 5h 7m.
What are all possible destination arrival airports?
The possible destination arrival airports from San Juan are Chicago O'Hare Airport and Chicago Midway Airport.
What is the time difference between destination and arrival?
The time difference between San Juan and Chicago is one hour, with Chicago being one hour behind San Juan.
Is there a direct flight from origin to destination?
Yes, there are direct flights from Luis Munoz Marin International Airport to Chicago O Hare Airport. Spirit Airlines offers a non-stop flight for $167, American Airlines for $430, and United Airlines for $463.
Are there convenient layover flights from San Juan to Chicago?
Yes, there are convenient layover flights from San Juan to Chicago. They include Spirit Airlines at $265, Frontier Airlines at $285, JetBlue at $342, American Airlines at $459, and United Airlines at $468.
What are the most convenient layover airports for the flight?
Consider layover airports such as Orlando International Airport with Spirit Airlines, Washington Dulles Airport with United Airlines, Miami International Airport with American Airlines, and New York John F Kennedy Airport with JetBlue.
Flights to Chicago
- Flights
- North America
- United States
- Illinois
- Chicago
➔ Flights To Vienna➔ Flights To Paris➔ Flights To Rome➔ Flights To London➔ Flights To Shanghai➔ Flights To Sydney➔ Flights To San Jose➔ Flights To Brussels➔ Flights To Nairobi➔ Flights To Munich➔ Flights To Cairo➔ Flights To Bengaluru➔ Flights To Dallas➔ Flights To Barcelona➔ Flights To Zurich➔ Flights To Malaga➔ Flights To Tokyo➔ Flights To Tirana➔ Flights To Dublin➔ Flights To Budapest➔ Flights To Buenos Aires➔ Flights To Istanbul➔ Flights To Singapore➔ Flights To Florence➔ Flights To Krakow➔ Flights To Tel Aviv➔ Flights To Copenhagen➔ Flights To Milan➔ Flights To Melbourne➔ Flights To Lisbon
- Flights
- Caribbean
- Puerto Rico
- San Juan