Flight deals from Chicago to San Juan

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Chicago to San Juan >

Fare Guide

Estimated lowest fares found within 7 days

The cheapest airline(s) flying from Chicago to San Juan is Spirit Airlines.

Travel Period: July 2024 - June 2025

The cheapest month(s) to fly from Chicago to San Juan is July.

Jul 2024
Aug 2024
Sep 2024
Oct 2024
Nov 2024
Dec 2024
Jan 2025
Feb 2025
Mar 2025
Apr 2025
May 2025
Jun 2025

The cheapest day(s) of the week to fly from Chicago to San Juan is Monday.

Sun Sunday
Mon Monday
Tue Tuesday
Wed Wednesday
Thu Thursday
Fri Friday
Sat Saturday

The cheapest time of the day to fly from Chicago to San Juan is in the morning.

Early Morning 12:01am - 06:00am

Morning 6:01am - 12:00pm

Afternoon 12:01pm - 6:00pm

Evening 6:01pm to 12:00am

12am

6am

12pm

6pm

Flight Schedules

Last Updated: Sun, 2 Jun, 2024

Depart Earliest
- Earliest
- Latest
Arrive
- Earliest
- Latest
Airline Filter by Airline
All
Total Duration
- Shortest
- Longest
Stopover
All
Availability
- M
- T
- W
- T
- F
- S
- S

23:20 - 05:00+ 1

ORD - SJU
23:20 (ORD)Chicago O'Hare International Airport
05:00 (SJU)San Juan Luis Munoz Marin Intl Airport + 1
American Airlines (AA 509)Boeing 737 800
4h 40m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

09:22 - 15:09

ORD - SJU
09:22 (ORD)Chicago O'Hare International Airport
15:09 (SJU)San Juan Luis Munoz Marin Intl Airport
United Airlines (UA 1996)Boeing 737 800
4h 47m
Direct
- M
- T
- W
- T
- F
- S
- S
Boeing 737 800

18:05 - 23:51

ORD - SJU
18:05 (ORD)Chicago O'Hare International Airport
23:51 (SJU)San Juan Luis Munoz Marin Intl Airport
United Airlines (UA 695)Boeing 737 800
4h 46m
Direct
- -
- -
- -
- -
- -
- S
- -
Boeing 737 800

Connecting Flights

05:45 - 09:20

MDW - TPA

13:00 - 15:50

TPA - SJU
05:45 (MDW)Chicago Midway Airport

13:00 (TPA)Tampa International Airport
09:20 (TPA)Tampa International Airport

15:50 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 575)Boeing 737 800

Southwest Airlines (WN 5301)Boeing 737 Max 8 Passenger
9h 05m (3h 40m)
TPA Tampa 3h 40m
- M
- -
- -
- -
- -
- -
- -

06:35 - 10:05

MDW - MCO

12:30 - 15:20

MCO - SJU
06:35 (MDW)Chicago Midway Airport

12:30 (MCO)Orlando International Airport
10:05 (MCO)Orlando International Airport

15:20 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 332)Boeing 737 800

Southwest Airlines (WN 4402)Boeing 737 Max 8 Passenger
7h 45m (2h 25m)
MCO Orlando 2h 25m
- M
- -
- -
- -
- -
- -
- -

08:10 - 11:45

MDW - MCO

15:10 - 18:00

MCO - SJU
08:10 (MDW)Chicago Midway Airport

15:10 (MCO)Orlando International Airport
11:45 (MCO)Orlando International Airport

18:00 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 2966)Boeing 737 700

Southwest Airlines (WN 2658)Boeing 737 800
8h 50m (3h 25m)
MCO Orlando 3h 25m
- M
- -
- -
- -
- -
- -
- -

08:10 - 11:45

MDW - MCO

12:30 - 15:20

MCO - SJU
08:10 (MDW)Chicago Midway Airport

12:30 (MCO)Orlando International Airport
11:45 (MCO)Orlando International Airport

15:20 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 2966)Boeing 737 700

Southwest Airlines (WN 4402)Boeing 737 Max 8 Passenger
6h 10m (45m)
MCO Orlando 45m
- M
- -
- -
- -
- -
- -
- -

09:10 - 13:05

ORD - MCO

15:10 - 18:00

MCO - SJU
09:10 (ORD)Chicago O'Hare International Airport

15:10 (MCO)Orlando International Airport
13:05 (MCO)Orlando International Airport

18:00 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 2985)Boeing 737 700

Southwest Airlines (WN 2658)Boeing 737 800
7h 50m (2h 05m)
MCO Orlando 2h 05m
- M
- -
- -
- -
- -
- -
- -

09:45 - 13:20

MDW - MCO

15:10 - 18:00

MCO - SJU
09:45 (MDW)Chicago Midway Airport

15:10 (MCO)Orlando International Airport
13:20 (MCO)Orlando International Airport

18:00 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 2967)Boeing 737 800

Southwest Airlines (WN 2658)Boeing 737 800
7h 15m (1h 50m)
MCO Orlando 1h 50m
- M
- -
- -
- -
- -
- -
- -

11:55 - 15:30

MDW - MCO

18:45 - 21:35

MCO - SJU
11:55 (MDW)Chicago Midway Airport

18:45 (MCO)Orlando International Airport
15:30 (MCO)Orlando International Airport

21:35 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 879)Boeing 737 700

Southwest Airlines (WN 4404)Boeing 737 Max 8 Passenger
8h 40m (3h 15m)
MCO Orlando 3h 15m
- M
- -
- -
- -
- -
- -
- -

12:35 - 15:25

MDW - BWI

19:40 - 23:40

BWI - SJU
12:35 (MDW)Chicago Midway Airport

19:40 (BWI)Baltimore Washington International Airport
15:25 (BWI)Baltimore Washington International Airport

23:40 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 1015)Boeing 737 Max 8 Passenger

Southwest Airlines (WN 4399)Boeing 737 Max 8 Passenger
10h 05m (4h 15m)
BWI Baltimore 4h 15m
- M
- -
- -
- -
- -
- -
- -

12:40 - 16:25

ORD - MCO

20:25 - 23:15

MCO - SJU
12:40 (ORD)Chicago O'Hare International Airport

20:25 (MCO)Orlando International Airport
16:25 (MCO)Orlando International Airport

23:15 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 5404)Boeing 737 700

Southwest Airlines (WN 4405)Boeing 737 800
9h 35m (4h)
MCO Orlando 4h
- M
- -
- -
- -
- -
- -
- -

12:40 - 16:25

ORD - MCO

18:45 - 21:35

MCO - SJU
12:40 (ORD)Chicago O'Hare International Airport

18:45 (MCO)Orlando International Airport
16:25 (MCO)Orlando International Airport

21:35 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 5404)Boeing 737 700

Southwest Airlines (WN 4404)Boeing 737 Max 8 Passenger
7h 55m (2h 20m)
MCO Orlando 2h 20m
- M
- -
- -
- -
- -
- -
- -

14:30 - 18:25

MDW - FLL

19:50 - 22:25

FLL - SJU
14:30 (MDW)Chicago Midway Airport

19:50 (FLL)Fort Lauderdale/Hollywood Intl Airport
18:25 (FLL)Fort Lauderdale/Hollywood Intl Airport

22:25 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 5658)Boeing 737 Max 8 Passenger

Southwest Airlines (WN 755)Boeing 737 800
6h 55m (1h 25m)
FLL Miami 1h 25m
- M
- -
- -
- -
- -
- -
- -

16:00 - 19:35

MDW - MCO

20:25 - 23:15

MCO - SJU
16:00 (MDW)Chicago Midway Airport

20:25 (MCO)Orlando International Airport
19:35 (MCO)Orlando International Airport

23:15 (SJU)San Juan Luis Munoz Marin Intl Airport
Southwest Airlines (WN 2969)Boeing 737 700

Southwest Airlines (WN 4405)Boeing 737 800
6h 15m (50m)
MCO Orlando 50m
- M
- -
- -
- -
- -
- -
- -

Sorry, there are no schedules matching your filters. Try removing one. reset

What’s the fastest flight time from Chicago to San Juan?

The fastest flight time for direct flights from Chicago to San Juan is 4 hours 40 minutes. Check latest flight schedules & prices on Wego.

What’s the most popular airline flying from Chicago to San Juan?

The most popular airline flying from Chicago to San Juan is United Airlines. Find the latest flight deals on Wego.

How far is San Juan from Chicago?

The flight distance between Chicago and San Juan is 3305km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 05:45. The last flight of the day departs at 23:20. See the full list of flight times on Wego.

How many airlines offer direct flights from Chicago to San Juan?

There are 2 airlines that offer direct flights from Chicago to San Juan. Find out the list of airlines on Wego.

Flight deals from Chicago to San Juan

Fare Guide

Estimated lowest fares found within 7 days

Flight Schedules

Last Updated: Sun, 2 Jun, 2024

Connecting Flights

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