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.

Why travel with Kiwi.com?
Best price

100+ million searches a day to find you the best available price.

Unique content

Explore unique options you won’t find anywhere else.

Travel hacks

Discover flight options and prices the airlines don’t want you to see.

3341 km
Distance
Duration
Mailbox
Receive exclusive deals by email.

By subscribing you agree to receive offers according to the conditions described in our Privacy Policy.

Travelers usually depart from Luis Muñoz Marín International, or Fernando Luis Ribas Dominicci when they travel from San Juan to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Rockford International, or Chicago Downtown Greyhound Station. The distance between San Juan and Chicago is 3341 km. The most popular airlines for this route are Spirit Airlines, Frontier Airlines, United Airlines, American Airlines, and Delta Air Lines. San Juan and Chicago have 401 direct flights per week.

Weekly direct flights

MondaysTuesdaysWednesdaysThursdaysFridaysSaturdaysSundays
Direct flights1111132
Fly direct with

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

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
Spirit AirlinesNKSNKNoOpens 24 days before flight
Closes 1 hours before flight
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
American AirlinesAALAAYesNo
Delta Air LinesDALDLYesOpens 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.

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

Kiwi.com

Latest COVID-19 restrictions

United States

Kiwi.com/COVID-19/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

Latest COVID-19 travel restrictions in United States – 06/2022
Your trip summary

Most travelers from Puerto Rico with proof of full COVID-19 vaccination can enter Chicago, MDW, but there are restrictions.

Departure

Travel restrictions
  • Travel is allowed with restrictions

  • No proof of negative pre-departure COVID-19 test results or recovery certificate

  • No quarantine for vaccinated travelers

Forms and documents
  • Mandatory proof of vaccination for the United States

Return

Travel restrictions
  • Travel is allowed

  • No proof of negative pre-departure COVID-19 test results or recovery certificate

  • No proof of a negative pre-departure COVID-19 test required

  • No quarantine required

Additional information
  • Masks are mandatory in certain settings

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.

Frequently asked questions

How long does it take to travel from San Juan to Chicago?
A one-way nonstop (direct) flight between San Juan and Chicago takes around 5.2 hours.
What is the flight distance between San Juan and Chicago?
The flight distance between San Juan and Chicago is 3341 km.
What airlines offer nonstop (direct) flights between San Juan and Chicago?
Several carriers operate flights between San Juan and Chicago. Airlines offering nonstop (direct) flights include American Airlines, United Airlines.
What are the most popular routes to and from San Juan?
Travelers frequently search for route combinations, such as San Juan and Orlando, New York, London, Madrid, Philadelphia, Barcelona, Fort Lauderdale, Paris, Washington, D.C., Hartford, Guadalajara, Minneapolis, Raleigh, Tampa, Boston, Nashville, Santo Domingo, Atlanta, Saint Thomas, Los Angeles.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and London, Dublin, Manchester, Toronto, Athens, Orlando, San Francisco, Hyderabad, Vilnius, New York, Las Vegas, Edinburgh, Denver, Bangkok, Minneapolis, Riga, Glasgow, Austin, Edmonton, Tallinn.
Which airports are there in San Juan?
San Juan is mainly served by Luis Muñoz Marín International. But there are other airports nearby, including Fernando Luis Ribas Dominicci.
What airports are near San Juan?
The main airport in San Juan is Luis Muñoz Marín International. It is also served by Aguadilla Rafael Hernandez, Mercedita, Eugenio María de Hostos.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, Dane County Regional, General Wayne A. Downing Peoria International, South Bend International, Fort Wayne International, Central Illinois Regional, Quad City International, Kalamazoo/Battle Creek International, Muskegon County.
Is it possible to combine flights, buses, and trains in one itinerary when traveling between San Juan and Chicago?
Yes, it's possible to combine different modes of transport between San Juan and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between San Juan and Chicago can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.
What is Virtual Interlining and how do I use it?
Which airlines fly between San Juan and Chicago?
When's the best time to travel between San Juan and Chicago?
What flights operate between San Juan and Chicago?
How many airports are there near San Juan?
How many airports are there near Chicago?
What time do nonstop (direct) flights between San Juan and Chicago depart?
What time do nonstop (direct) flights between San Juan and Chicago arrive?
What time do flights between San Juan and Chicago depart?
What time do flights between San Juan and Chicago arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.

Explore alternative trips

Flights from San Juan

Flights to Chicago

Popular routes

Find the best connection from San Juan to Chicago

Search, compare, and book flights, trains, or buses to get there.

Search flights, trains & buses