Cheap flights Chicago — San Juan (CHI — SJU)

Good to know - Cheap tickets Chicago — San Juan

Cheapest flight found $60
Minimal flight time 4h 9m
Flight distance 3306 km
Most popular airline Spirit Airlines

Airfare Chicago – San Juan by month

Here you can find out in what months how much a ticket Chicago – San Juan costs to buy cheap plane tickets.

Month One-way Round-trip
October 2025
September 2025
August 2025
July 2025
June 2025
May 2025
April 2025
March 2025
February 2025
January 2025
December 2024
November 2024

Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.

Schedule of direct flights Chicago — San Juan

Departure Arrival Flight days Flight Airlines Flight time Airports
01:00 06:32 tue G6400 GlobalX (Blue Livery) 4h 32m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
01:15 06:47 mon G6400 GlobalX (Blue Livery) 4h 32m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
06:30 12:39 sun G6400 GlobalX (Blue Livery) 4h 9m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
06:40 12:23 sat NK1877 Spirit Airlines 4h 43m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
07:20 13:58 sat UA1996 United Airlines 4h 38m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
08:04 13:45 daily NK261 Spirit Airlines 4h 41m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
08:39 15:15 wed, thu NK261 Spirit Airlines 4h 36m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
08:39 14:15 tue, wed, sat, sun NK261 Spirit Airlines 4h 36m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
08:40 14:25 sun WN2420 Southwest Airlines 4h 45m Chicago Midway International Airport — Luis Munoz Marin International Airport Select dates
08:43 14:33 daily AA2852 American Airlines 4h 50m O'Hare International Airport — Luis Munoz Marin International Airport Select dates
All routes

Sales of tickets from Chicago to San Juan in the last 48 hours

2025-08-26 one-way

2025-08-28 one-way

2025-08-28 one-way

Flights Chicago — San Juan

The selection of cheap flights Chicago — San Juan

Here you can find and purchase the cheapest flights Chicago — San Juan from $60 and Chicago — San Juan — Chicago from $96.

The price of the flight Chicago — San Juan (Puerto Rico) — Chicago from $96 (round-trip).

The average price of the flight Chicago — San Juan (Puerto Rico) — Chicago $322 (round-trip).

Low cost flights Chicago — San Juan (CHI — SJU)

The distance between Chicago and San Juan 2054 miles (or 3306 kilometres).

The time difference between Chicago and San Juan is 1 h.

Minimal flight time from Chicago to San Juan 4h 9m.

LowCostClub always do a comparison of airfares Chicago — San Juan with several airlines (include GlobalX (Blue Livery), Spirit Airlines, United Airlines). They will always give you all available options so you can find the cheapest flight to San Juan. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Chicago — San Juan. Last week, for instance, the cheapest round-trip prices stood at $96 while the cheapest one-way price that was available within the last week cost $60

Routes from nearby cities to San Juan

A flight from a neighbouring city can help you save money on plane tickets.

The most frequent flight to San Juan is from Madison. The cheapest airfare can be purchased with a flight from Grand Rapids from $73. The nearest airports from Chicago with a flight to San Juan are in Fort Wayne.

Popular International routes from Chicago

Popular routes from San Juan

If you are going to fly from San Juan, then study the popular flights. The most popular flights from San Juan:

Popular domestic routes from Chicago

FAQ about Chicago — San Juan

Yes, they do: G6400, NK1877, UA1996, NK261, WN2420, AA2852, NK2535, NK1635, UA695, NK263

Yes, you can fly from Chicago to San Juan. Chicago has 8 airports (Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport) for flights. GlobalX (Blue Livery), Spirit Airlines, United Airlines, Southwest Airlines, American Airlines depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through 21 Air, ABX Air, Air Canada, Amerijet International, Atlas Air, Avelo Airlines, Avianca, Cape Air, Cargolux, Copa Airlines, Delta Air Lines, DHL, FedEx, Frontier (Cali the Mountain Lion Livery), Iberia, Jet Linx Aviation, JetBlue, Maersk Air Cargo, NetJets, Sun Country Airlines, UPS.

A direct flight lasts an average of 4h 9m, during which time the aircraft covers a distance of 3306 km.

The price of flights Chicago — San Juan starts from $60.

Planes fly Chicago — San Juan 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun

In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport. In San Juan — Luis Munoz Marin International Airport, Isla Grande.

The following flights fly between Chicago and San Juan: G6400, G6400, G6400, NK1877, UA1996, NK261, NK261, NK261, WN2420, AA2852, UA1996, WN2420, UA1996, UA1996, UA1996, NK2535, NK1635, NK2535, UA695, NK1635, NK263, NK263, NK263, G6400, G6400, G6400, G6400

High season is considered to be and the cheapest month is . Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Chicago — San Juan flight deals.

The following airlines have direct flights Chicago — San Juan: GlobalX (Blue Livery), Spirit Airlines, United Airlines, Southwest Airlines, American Airlines.

All the following airlines flights Chicago — San Juan: 21 Air, ABX Air, Air Canada, American Airlines, Amerijet International, Atlas Air, Avelo Airlines, Avianca, Cape Air, Cargolux, Copa Airlines, Delta Air Lines, DHL, FedEx, Frontier (Cali the Mountain Lion Livery), GlobalX (Blue Livery), Iberia, Jet Linx Aviation, JetBlue, Maersk Air Cargo, NetJets, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Airlines, UPS.

Low price calendar

We use cookies and similar technologies for different purposes. Read the privacy policy. If you use the site you agree to them.