Chicago to San Juan flights
Routavio compares airline fares from several flight booking sites. The lowest one-way fare it found for Chicago to San Juan is €65 with Frontier Airlines (checked on 5 Nov 2026).
Your next trip, last seen at €65
Lowest observedFrontier Airlines · Non-stop · One wayWhen to fly
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The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.
One-way fare
- 13 Jan€107
- Lowest observed
- €65, departing 11 Jan 2027 (Last checked: 5 Nov 2026)One-way fareCheck live prices for this route
- Round trip
- €191, departing 14 Jan 2027, back 19 Jan 2027 (Last checked: 12 Nov 2026)
- Non-stop, one way
- €65, departing 11 Jan 2027 (Last checked: 6 Nov 2026)
- Airlines seen
- Frontier Airlines, United Airlines, Allegiant Air, JetBlue
- Fastest observed flight time
- 4h 39m
- Non-stop
- Yes
About this route
Explore the fares we observed from Chicago to San Juan. Prices move often, so pick your dates to see the latest options.
- Route distance
- 3,305 km
- Fastest observed flight time
- 4h 39m
- Airlines seen
- Frontier Airlines, United Airlines, Allegiant Air, JetBlue
- Alternative airports
- CGX, DPA, MDW, PWK, RFD, SIG
Route-level information; individual journeys vary.
A clearer picture of your fare
If the observed fare for this date drops, we will email you. At most one message a day.
Non-stop airlines seen on this route
| Airline | Non-stop days / priced days |
|---|---|
| Frontier Airlines | 34 / 74 |
Departure days with a non-stop fare checked in the last 14 days. A carrier listed here had a non-stop fare on at least 3 days; schedules may differ.
Airport to city: straight-line distance
- Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
- Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
- Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.
- Fernando Luis Ribas Dominicci Airport (SIG) → San Juan, city gazetteer reference point (18.4663, -66.1057): ≈ 1 km.
- Luis Munoz Marin International Airport (SJU) → San Juan, city gazetteer reference point (18.4663, -66.1057): ≈ 11 km.
Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.
Observed fares by departure date
| Departure | Fare | Seen on |
|---|---|---|
| €143 | 6 Nov 2026 | |
| €117 | 5 Nov 2026 | |
| €126 | 5 Nov 2026 | |
| €126 | 5 Nov 2026 | |
| €127 | 5 Nov 2026 | |
| €126 | 6 Nov 2026 | |
| €127 | 5 Nov 2026 | |
| €91 | 6 Nov 2026 | |
| €79 | 5 Nov 2026 | |
| €110 | 5 Nov 2026 | |
| €127 | 5 Nov 2026 | |
| €113 | 5 Nov 2026 | |
| €107 | 5 Nov 2026 | |
| €106 | 5 Nov 2026 | |
| €105 | 5 Nov 2026 | |
| €107 | 5 Nov 2026 | |
| €105 | 6 Nov 2026 | |
| €105 | 5 Nov 2026 | |
| €104 | 6 Nov 2026 | |
| €65 | 5 Nov 2026 |
One-way fares. Each row is one price we saw for that departure day on the date shown, not a guaranteed fare.
Frequently asked
How much is a flight from Chicago to San Juan?
The lowest fare Routavio has observed is €65, found on 5 Nov 2026.
Are there direct flights from Chicago to San Juan?
Yes. Published schedules report non-stop flights on this route with Frontier Airlines, United Airlines, American Airlines.
Which airlines fly from Chicago to San Juan?
Routavio has seen these carriers on the route: Frontier Airlines, United Airlines, Allegiant Air, JetBlue.
How long does the flight from Chicago to San Juan take?
Across the 116 fares Routavio observed, the average journey time is 9h 52m, including any stops. Individual departures vary; the fastest observed flight is listed in the route facts above.
How many of the observed Chicago to San Juan fares were non-stop?
39 of the 121 fares we observed were non-stop; the rest included at least one stop. That describes our observations, not every flight that operates.
How much is a round trip from Chicago to San Juan?
Cheapest round trip: €191, departing 14 Jan 2027, back 19 Jan 2027 (checked 12 Nov 2026).
How much is a non-stop flight from Chicago to San Juan?
Cheapest non-stop one-way fare: €65, departing 11 Jan 2027 (checked 6 Nov 2026).
Which airlines had non-stop offers on at least 3 departure dates from Chicago to San Juan?
For Chicago to San Juan, examples of observed one-way non-stop offers checked within the last 14 days: Frontier Airlines (34). Each number counts distinct departure dates, not weekly flights; check current availability in search.
How observed prices work, what "No data" means and what a fare includes: Read the flight price guide · Price and schedule freshness on Routavio
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Recently observed fares. Prices may change.