Cheap flights from Chicago to San Juan from £166
Trusted by millions
Kiwi.com Guarantee for stress-free travel
One search, all the best deals
Explore flight deals to San Juan
Not happy with the results? Try some of our useful filters
Search by stops
Search by carrier
Search by price
Search by departure date
Not happy with the results? Try some of our useful filters
Search by stops
Search by carrier
Search by price
Search by departure date
How much do flights to San Juan cost?
Getting from San Juan airport to the city center
Fastest options: taxi or ride-hailing services. Best value: public buses and shared shuttles.
Transport Option | Typical Time | Typical Cost | Frequency | Best For |
|---|---|---|---|---|
20-40 min | $15-$25 (fixed zone rates; metered to other areas) | on-demand 24/7 (traffic dependent) | convenience with luggage | |
20-40 min | $12-$30 (varies with demand and destination) | on-demand 24/7 (traffic dependent) | app-based convenience | |
45-75 min | $0.75 (exact change required) | every 30–60 min (traffic dependent) | budget travelers | |
20-45 min | $0-$20 (complimentary or fee varies by hotel) | scheduled by hotel (traffic dependent) | hotel guests | |
20-40 min | $35-$80 (per day; varies by company and vehicle) | on-demand (traffic dependent) | exploring the island | |
30-60 min | $10-$20 (per person; multiple stops) | scheduled departures (traffic dependent) | solo travelers on budget |
Notes:
- Prices in USD; table created in 2025 and subject to change.
- Taxis from SJU operate on fixed zone rates to tourist areas like Condado, Isla Verde, and Old San Juan.
- Public bus service is limited and may require transfers to reach central tourist areas.
- Ride-hailing pickup is located at designated areas outside the terminal.
- We recommend checking official transport websites for your travel planning.
Updated: December 2025
Key info about flying to San Juan
Weekly direct flights
Discover the top airlines offering direct flights from Chicago to San Juan in the next month. You’ll find the number of daily direct flights per airline in the chart.
| Airline | Mon 11.05 | Tue 12.05 | Wed 13.05 | Thu 14.05 | Fri 15.05 | Sat 16.05 | Sun 17.05 |
|---|---|---|---|---|---|---|---|
| --- | --- | --- | --- | 2 | 2 | 2 | |
| --- | --- | --- | --- | --- | --- | --- | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 6 total | Daily flights: 0.86 average | Most flights: Friday 2 flights |
| Airline | Mon 18.05 | Tue 19.05 | Wed 20.05 | Thu 21.05 | Fri 22.05 | Sat 23.05 | Sun 24.05 |
|---|---|---|---|---|---|---|---|
| 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
| --- | --- | --- | 1 | 1 | 1 | 1 | |
| --- | --- | --- | --- | --- | --- | 1 | |
| Weekly flights: 19 total | Daily flights: 2.71 average | Most flights: Monday 2 flights |
| Airline | Mon 25.05 | Tue 26.05 | Wed 27.05 | Thu 28.05 | Fri 29.05 | Sat 30.05 | Sun 31.05 |
|---|---|---|---|---|---|---|---|
| 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 21 total | Daily flights: 3 average | Most flights: Monday 2 flights |
| Airline | Mon 01.06 | Tue 02.06 | Wed 03.06 | Thu 04.06 | Fri 05.06 | Sat 06.06 | Sun 07.06 |
|---|---|---|---|---|---|---|---|
| 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
| 1 | --- | --- | --- | --- | --- | --- | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 15 total | Daily flights: 2.14 average | Most flights: Monday 2 flights |
Check-in for a flight from Chicago to San Juan
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| Frontier Airlines | FFT | F9 | No |
| JetBlue Airways | JBU | B6 | No |
| Allegiant Air | AAY | G4 | No |
| United Airlines | UAL | UA | No |
| WestJet | WJA | WS | No |
Online check-in is not available for these airlines.
Weather in San Juan
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | 27°C | 22°C |
| February | 27°C | 22°C |
| March | 27°C | 22°C |
| April | 28°C | 23°C |
| May | 29°C | 24°C |
| June | 30°C | 25°C |
| July | 30°C | 25°C |
| August | 30°C | 25°C |
| September | 30°C | 25°C |
| October | 29°C | 25°C |
| November | 28°C | 24°C |
| December | 27°C | 23°C |
14 day forecast
Frequently asked questions
Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any origin and destination in the world by plane. Find the cheapest routes and best deals, as well as the best dates to travel.
Explore alternative trips
Flights from Chicago
Flights to San Juan
Popular routes
Airports near Chicago
Airports near San Juan
Download our app