Cheap flights from San Juan to Chicago from £102
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How much do flights to Chicago cost?
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 12.10 | Tue 13.10 | Wed 14.10 | Thu 15.10 | Fri 16.10 | Sat 17.10 | Sun 18.10 |
|---|---|---|---|---|---|---|---|
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| Weekly flights: 14 total | Daily flights: 2 average | Most flights: Monday 1 flights |
| Airline | Mon 19.10 | Tue 20.10 | Wed 21.10 | Thu 22.10 | Fri 23.10 | Sat 24.10 | Sun 25.10 |
|---|---|---|---|---|---|---|---|
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| Weekly flights: 14 total | Daily flights: 2 average | Most flights: Monday 1 flights |
| Airline | Mon 26.10 | Tue 27.10 | Wed 28.10 | Thu 29.10 | Fri 30.10 | Sat 31.10 | Sun 01.11 |
|---|---|---|---|---|---|---|---|
| 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 02.11 | Tue 03.11 | Wed 04.11 | Thu 05.11 | Fri 06.11 | Sat 07.11 | Sun 08.11 |
|---|---|---|---|---|---|---|---|
| 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 |
Check-in for a flight from San Juan to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| Frontier Airlines | FFT | F9 | No |
| American Airlines | AAL | AA | No |
| JetBlue Airways | JBU | B6 | No |
| - | |||
| United Airlines | UAL | UA | No |
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.
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