Cheap flights from San Juan to Chicago from £165
Trusted by millions
Kiwi.com Guarantee for stress-free travel
One search, all the best deals
Explore flight deals to Chicago
Not happy with the results? Try some of our useful filters
Search by stops
Search by price
Search by departure date
Not happy with the results? Try some of our useful filters
Search by stops
Search by price
Search by departure date
How much do flights to Chicago cost?
Cheapest one-way trip | £165 |
|---|---|
Cheapest nonstop round-trip | £443 |
Cheapest round-trip | £314 |
Average round-trip | £383 |
Nonstop flights in June | £160 – £364 |
Getting from Chicago's airport to the city center
Fastest options: CTA Blue Line train from O'Hare. Best value: CTA Orange Line from Midway or shared ride services.
How to get from O'Hare International Airport (ORD) to Chicago?
Transport Option | Typical Time | Typical Cost | Frequency | Best For |
|---|---|---|---|---|
40-50 min | $5; standard fare | every 5–10 min (traffic dependent) | budget travelers to Loop | |
60-90 min | $2 – $5; combined bus and Metra fare | every 20–30 min (traffic dependent) | northwest suburbs connection | |
35-70 min | $45 – $65; metered; varies by traffic | on-demand 24/7 (traffic dependent) | door-to-door with luggage | |
35-70 min | $35 – $75; surge pricing may apply | on-demand 24/7 (traffic dependent) | app-based convenience | |
35-70 min | $60 – $120; pre-booked; fixed rate | by reservation (traffic dependent) | groups or business travel |
How to get from Chicago Midway International Airport (MDW) to Chicago?
Transport Option | Typical Time | Typical Cost | Frequency | Best For |
|---|---|---|---|---|
25-30 min | $5; standard fare | every 6–12 min (traffic dependent) | quick access to Loop | |
20-45 min | $30 – $45; metered; varies by traffic | on-demand 24/7 (traffic dependent) | door-to-door convenience | |
20-45 min | $25 – $50; surge pricing may apply | on-demand 24/7 (traffic dependent) | flexible pickup location |
Notes:
- Prices in USD; table created in 2025 and subject to change.
- CTA Ventra cards or contactless payment accepted on Blue and Orange Lines.
- Taxis are metered; ride-hailing prices vary with demand. Road traffic can significantly affect journey times.
- We recommend checking official transport websites for your travel planning.
Updated: December 2025
Key info about flying to Chicago
Weekly direct flights
Discover the top airlines offering direct flights from San Juan to Chicago in the next month. You’ll find the number of daily direct flights per airline in the chart.
| 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 | |
| --- | --- | --- | 1 | 1 | 1 | 1 | |
| Weekly flights: 12 total | Daily flights: 1.71 average | Most flights: Thursday 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 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 14 total | Daily flights: 2 average | Most flights: Monday 2 flights |
| Airline | Mon 08.06 | Tue 09.06 | Wed 10.06 | Thu 11.06 | Fri 12.06 | Sat 13.06 | Sun 14.06 |
|---|---|---|---|---|---|---|---|
| 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 14 total | Daily flights: 2 average | Most flights: Monday 2 flights |
| Airline | Mon 15.06 | Tue 16.06 | Wed 17.06 | Thu 18.06 | Fri 19.06 | Sat 20.06 | Sun 21.06 |
|---|---|---|---|---|---|---|---|
| 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
| --- | --- | --- | --- | --- | --- | --- | |
| Weekly flights: 14 total | Daily flights: 2 average | Most flights: Monday 2 flights |
Check-in for a flight from San Juan to Chicago
| 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 |
| Air Canada | ACA | AC | Yes |
Online check-in is not available for these airlines.
Weather in Chicago
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | -1°C | -6°C |
| February | 0°C | -5°C |
| March | 6°C | 0°C |
| April | 11°C | 5°C |
| May | 17°C | 10°C |
| June | 22°C | 16°C |
| July | 26°C | 20°C |
| August | 25°C | 19°C |
| September | 22°C | 16°C |
| October | 15°C | 10°C |
| November | 8°C | 3°C |
| December | 2°C | -1°C |
14 day forecast
Chicago travel tips
Visit Chicago's semi-secret bars
Although the days of Prohibition are long gone, there are still back-street bars. They are shrouded in mystery, and their addresses are passed from mouth to mouth. Among them, there are quite expensive bars (for example, The Milk Room) and establishments that are affordable for tourists. For example, The Drifter, whose walls are steeped in history. Or you can visit The Library at Gilt Bar, Booze Box, Blind Barber, and others.
Marvel at modern graffiti art in Chicago
For modern graffiti, head to Milwaukee St. This street is a one-story America during the day and a very party area at night. There you will find interesting graffiti and stylish bars in a hipster atmosphere.
Learn more about the history of Chicago and the Great Chicago Fire
The City History Museum in Chicago will tell you more about this city and the Great Chicago Fire that killed 300 people and left 100,000 homeless. There are also many exhibits related to the life and death of Abraham Lincoln. The entrance to the museum costs $19 (€ 16).
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 San Juan
Flights to Chicago
Popular routes
Airports near San Juan
Airports near Chicago
Download our app