⚡ Fare recorded April 25, 2026 · Prices change daily

Chicago to San Juan flights

Chicago (MDW) to San Juan (SJU): 2,059 miles (3,314 km) great-circle, about 4h 35m nonstop by our estimate. Cheapest fare observed: $232 round-trip on Frontier, with 1 stop, departing April 26, 2026.

F9FrontierF92292
Depart
MDW
Chicago, USA
06:00
2026-04-26
✈
Arrive
SJU
San Juan, United States
Returns 06:30
2026-05-03
Stops
1 stop
Distance
2,059 mi
Est. nonstop time
4h 35m
Trip type
Round-trip
$232
Round-trip · per person
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About this flight

When did the cheapest Chicago to San Juan fare fly?

$232 round-trip, Frontier F92292, departing 2026-04-26 at 06:00, returning 2026-05-03. The recorded itinerary left on a Sunday, returning on a Sunday 7 nights later; the fare was observed 1 day before departure. "Book this flight" opens Kiwi.com with the same airline and dates.

Route facts

How far is Chicago from San Juan?

  • Distance: 2,059 miles (3,314 km) great-circle, heading southeast.
  • Estimated nonstop flight time: about 4h 35m.
  • Departure airport: Chicago Midway International Airport (MDW), Chicago, United States, UTC-5 on April 26, 2026.
  • Arrival: Luis Munoz Marin International Airport (SJU), United States, UTC-4 on April 26, 2026.
  • Time difference: San Juan is 1 hour ahead of Chicago on the recorded date.
  • Route type: domestic, within United States.
  • Arrival airport elevation: 9 ft.
  • Recorded itinerary: Frontier F92292, 1 stop, round-trip, 7 days between departure and return.
Fare comparison

How does the Chicago to San Juan fare compare with other routes from MDW?

At $232, it ranked 12th of the 30 round-trip fares we recorded from MDW (median $316). That is 11.3 cents per great-circle mile (round-trip price over one-way distance), below the MDW median of 22.1 cents across 30 round-trip routes.

Routes from MDW of similar length: Guatemala City (1,887 mi) at $796 and San Francisco (1,850 mi) at $424.

Frontier had the cheapest fare on 11 of 30 MDW routes. It is the 11th longest of the 30 routes we track from MDW.

Other ways in

What did other cities pay to fly to San Juan?

Of 20 departure airports with a fare to San Juan, Chicago (MDW) ranked 13th at $232. Lowest: $127 from Orlando (MCO); highest: $632 from Washington DC (IAD); 7 nonstop. Cheapest-fare airlines (routes): Frontier (9), Spirit (4), American Airlines (2), JetBlue (2), Southwest (1) and United Airlines (1), plus 1 more.

Sources

Where do these numbers come from?

Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, America/Puerto_Rico; flight time is our estimate.

FAQ

Chicago to San Juan flight questions

How far is Chicago from San Juan by plane?

+
Chicago is about 2,059 miles (3,314 km) from San Juan on a great-circle line from Chicago Midway International Airport (MDW) to Luis Munoz Marin International Airport (SJU), heading southeast. It is the 11th longest of the 30 routes we track from MDW. The recorded itinerary had 1 stop, so the distance flown was longer.

How long is the flight from Chicago to San Juan?

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About 4h 35m nonstop by our estimate for 2,059 miles (500 mph cruise plus 30 minutes, not a timetable). The recorded Frontier fare was with 1 stop. 20 airports in our feed had a fare to San Juan; this one ranked 13th, and 7 of the 20 were nonstop.

What is the time difference between Chicago and San Juan?

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On April 26, 2026, Chicago was on UTC-5 (America/Chicago) and San Juan on UTC-4 (America/Puerto_Rico), so San Juan was 1 hour ahead of Chicago: noon in Chicago was 13:00 in San Juan. Daylight saving changes it: in mid-January 2026 the gap is San Juan 2 hours ahead, in mid-July San Juan 1 hour ahead.

How much is a flight from Chicago to San Juan?

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As observed on April 25, 2026: $232 per person round-trip on Frontier flight F92292, departing April 26, 2026, returning May 3, 2026, with 1 stop. At $232, it ranked 12th of the 30 round-trip fares we recorded from MDW (median $316). That is 11.3 cents per great-circle mile (round-trip price over one-way distance), below the MDW median of 22.1 cents across 30 round-trip routes. Prices change daily, so check the live fare.

Is there a nonstop flight from Chicago to San Juan?

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The cheapest recorded fare had 1 stop; our feed keeps only the cheapest fare per route, so a pricier nonstop may exist. Into San Juan, 7 of the 20 recorded fares were nonstop. From MDW, 7 of 30 were. Routes from MDW of similar length: Guatemala City (1,887 mi) at $796 and San Francisco (1,850 mi) at $424.

Which airports serve flights from Chicago to San Juan?

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It departs Chicago Midway International Airport (MDW) in Chicago, United States, and arrives at Luis Munoz Marin International Airport (SJU) in San Juan, United States. A domestic United States flight. Frontier had the cheapest fare on 11 of 30 MDW routes.

Where else near San Juan can you fly from Chicago?

Miami (MIA) $138Fort Lauderdale (FLL) $160Orlando (ORL) $154Tampa (TPA) $178Atlanta (ATL) $105Washington (WAS) $217All flights from Chicago →

Other cities with flights to San Juan

From Orlando (MCO) $127From Philadelphia (PHL) $134From Tampa (TPA) $142From Punta Cana (PUJ) $148From Newark (EWR) $150From Fort Lauderdale (FLL) $163

Ready to fly?

Book Frontier MDW → SJU · $232 →