Good to know - Cheap tickets Chicago — San Juan
| Minimal flight time | 4h 31m |
|---|---|
| Flight distance | 3306 km |
| Most popular airline | United Express |
| Round-trip from | $53 |
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 |
|---|---|---|
| December 2026 | ||
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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 | |
|---|---|---|---|---|---|---|---|
| 07:40 | 13:18 | sat | UA795 | United Express | 4h 38m | O'Hare International Airport — Luis Munoz Marin International Airport | Select dates |
| 08:00 | 13:40 | sun | WN2232 | Southwest Airlines | 4h 40m | Chicago Midway International Airport — Luis Munoz Marin International Airport | Select dates |
| 08:06 | 13:49 | tue | AA3276 | American Eagle | 4h 43m | O'Hare International Airport — Luis Munoz Marin International Airport | Select dates |
| 08:26 | 14:09 | mon, thu, fri, sat, sun | AA3276 | American Eagle | 4h 43m | O'Hare International Airport — Luis Munoz Marin International Airport | Select dates |
| 08:49 | 14:44 | daily | UA1996 | United Express | 4h 55m | O'Hare International Airport — Luis Munoz Marin International Airport | Select dates |
| 08:50 | 14:25 | sat | WN2232 | Southwest Airlines | 4h 35m | Chicago Midway International Airport — Luis Munoz Marin International Airport | Select dates |
| 09:48 | 16:28 | tue | AA3304 | American Eagle | 4h 40m | O'Hare International Airport — Luis Munoz Marin International Airport | Select dates |
| 09:48 | 15:28 | tue | AA2519 | American Eagle | 4h 40m | O'Hare International Airport — Luis Munoz Marin International Airport | Select dates |
| 12:29 | 18:00 | daily | NK2205 | Spirit Airlines | 4h 31m | O'Hare International Airport — Luis Munoz Marin International Airport | Select dates |
| 14:20 | 19:59 | thu, fri, sat | UA695 | United Express | 4h 39m | O'Hare International Airport — Luis Munoz Marin International Airport | Select dates |
Popular airlines flying Chicago — San Juan
Flight Chicago – San Juan is served by 24 airlines. 4 airlines operate direct flights.
Airlines with direct flights
Other airlines flying with transfers
Dynamics airfare Chicago — San Juan by month for the last year
according to LowCost.Club for the last year
The airfare depends on the departure date. Our chart shows the low season prices on route Chicago — San Juan
The graph shows that booking flights Chicago — San Juan is best planned for February and flights Chicago — San Juan — Chicago in the month of February.
Flights Chicago — San Juan
The selection of cheap flights Chicago — San Juan
The price of the flight Chicago — San Juan (Puerto Rico) — Chicago from $53 (round-trip).
The average price of the flight Chicago — San Juan (Puerto Rico) — Chicago $382 (round-trip).
- Departure city: Chicago
- IATA code of the city of origin: CHI
- Departure 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
- Departure country: United States
- Destination city: San Juan
- IATA code of the destination city: SJU
- Destination airports: Luis Munoz Marin International Airport, Isla Grande
- Destination country: Puerto Rico
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 31m.
Routes from nearby cities to San Juan
A flight from a neighbouring city can help you save money on plane tickets.
The closest airports to Chicago with a flight to San Juan are in South Bend.
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
Are there any direct flights Chicago — San Juan?
Yes, they do: UA795, WN2232, AA3276, UA1996, AA3304, AA2519, NK2205, UA695, NK586, AA1758
Can we fly from Chicago to San Juan?
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. United Express, Southwest Airlines, American Eagle, Spirit Airlines depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through ABX Air, Air Canada, Arajet, Atlas Air, Avelo Airlines, avianca, Cape Air, Cargolux, Contour Aviation, Copa Airlines, Delta Connection, DHL, FedEx, Frontier (Penny the Owl Livery), GlobalX, Iberia, Jet Linx Aviation, JetBlue, NetJets, Phoenix Air, Southern Airways Express, Sun Country Airlines, UPS, WestJet.
How long does it take to fly from Chicago to San Juan?
A direct flight lasts an average of 4h 31m, during which time the aircraft covers a distance of 3306 km.
How much do flights Chicago — San Juan cost?
The price of flights Chicago — San Juan starts from $53.
What days does the plane fly Chicago — San Juan?
Planes fly Chicago — San Juan 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun
What airports are there in Chicago and San Juan?
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.
What flights are currently flying from Chicago to San Juan?
The following flights fly between Chicago and San Juan: UA795, WN2232, AA3276, AA3276, UA1996, WN2232, AA3304, AA2519, NK2205, UA695, UA695, NK586, AA1758
What month is the cheapest to fly from Chicago to San Juan?
High season is considered to be December and the cheapest month is February. Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Chicago — San Juan flight deals.
Which airlines direct fly from Chicago to San Juan?
The following airlines have direct flights Chicago — San Juan: United Express, Southwest Airlines, American Eagle, Spirit Airlines.
Which airlines fly from Chicago to San Juan?
All the following airlines flights Chicago — San Juan: ABX Air, Air Canada, American Eagle, Arajet, Atlas Air, Avelo Airlines, avianca, Cape Air, Cargolux, Contour Aviation, Copa Airlines, Delta Connection, DHL, FedEx, Frontier (Penny the Owl Livery), GlobalX, Iberia, Jet Linx Aviation, JetBlue, NetJets, Phoenix Air, Southern Airways Express, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United Express, UPS, WestJet.