San Juan to Chicago flights from £261
Flights starting at £261. Choose between Spirit Airlines, Frontier Airlines, or United Airlines to find the best price.
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Tips to know when travelling to Chicago
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£395 | |
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Weekly direct flights
Mondays | Tuesdays | Wednesdays | Thursdays | Fridays | Saturdays | Sundays | |
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Direct flights | 1 | 1 | 1 | 1 | 1 | 3 | 2 |
American Airlines on Mondays, Tuesdays, Wednesdays, Thursdays, Fridays, Saturdays, and Sundays.
United Airlines on Saturdays, and Sundays.
Check-in for a flight from San Juan to Chicago
Name | Carrier code | IATA Code | Passport needed during booking | Online check-in available |
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Spirit Airlines | NKS | NK | No | Opens 24 days before flight Closes 1 hours before flight |
Frontier Airlines | FFT | F9 | No | Opens 24 days before flight Closes 1 hours before flight |
United Airlines | UAL | UA | Yes | No |
American Airlines | AAL | AA | Yes | No |
Delta Air Lines | DAL | DL | Yes | Opens 24 days before flight Closes 1 hours before flight |
Chicago travel tips
1) 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. |
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2) 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. |
3) 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). |
United States COVID-19 travel restrictions

Latest COVID-19 restrictions
United States
Travel is allowed with restrictions
No proof of negative pre-departure COVID-19 test results or recovery certificate
No quarantine for vaccinated travelers

Most travelers from Puerto Rico with proof of full COVID-19 vaccination can enter Chicago, MDW, but there are restrictions.
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Information is provided as guidance only and accurate at the time of publishing. Always check government websites and airline materials before booking and traveling.
Learn more about COVID-19 restrictions in United States in our dedicated Stories article.
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