Cheap flights from San Juan, United States to Chicago, IL
Kiwi-Code uncovers prices airlines don't want you to see.
Use our flexible filters to tailor your search.
Look out for the travel hack star icon for even cheaper fares.
Tips to know when travelling to Chicago
Search by stops
- Nonstop
- Up to 1 stop
- Up to 2 stops
Search by carrier
Search by price
Search by departure date
One-way trips
Updated:
By subscribing you agree to receive offers according to the conditions described in our Privacy Policy.
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 table.
Weekly direct flights for Mon 13.05 - Sun 19.05
| Airline | Mon 13.05 | Tue 14.05 | Wed 15.05 | Thu 16.05 | Fri 17.05 | Sat 18.05 | Sun 19.05 |
|---|---|---|---|---|---|---|---|
| 1 | 1 | 1 | --- | 1 | 1 | 1 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 1 |
Weekly direct flights for Mon 20.05 - Sun 26.05
| Airline | Mon 20.05 | Tue 21.05 | Wed 22.05 | Thu 23.05 | Fri 24.05 | Sat 25.05 | Sun 26.05 |
|---|---|---|---|---|---|---|---|
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 2 |
Weekly direct flights for Mon 27.05 - Sun 02.06
| Airline | Mon 27.05 | Tue 28.05 | Wed 29.05 | Thu 30.05 | Fri 31.05 | Sat 01.06 | Sun 02.06 |
|---|---|---|---|---|---|---|---|
| 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 2 |
Weekly direct flights for Mon 03.06 - Sun 09.06
| Airline | Mon 03.06 | Tue 04.06 | Wed 05.06 | Thu 06.06 | Fri 07.06 | Sat 08.06 | Sun 09.06 |
|---|---|---|---|---|---|---|---|
| 1 | 1 | 2 | 2 | 2 | 2 | 2 | |
| 1 | 1 | 1 | 1 | 1 | 1 | 2 |
Check-in for a flight from San Juan to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking | Online check-in available |
|---|---|---|---|---|
| Spirit Airlines | NKS | NK | No | Opens 24 days before flight Closes 1 hours before flight |
| United Airlines | UAL | UA | Yes | No |
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). |
Weather in Chicago
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | 0°C | -6°C |
| February | 0°C | -5°C |
| March | 6°C | 0°C |
| April | 11°C | 4°C |
| May | 17°C | 10°C |
| June | 22°C | 16°C |
| July | 25°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
Frequently asked questions
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 from San Juan to Orlando
- Flights from San Juan to New York
- Flights from San Juan to London
- Flights from San Juan to Madrid
- Flights from San Juan to Philadelphia
- Flights from San Juan to Barcelona
- Flights from San Juan to Fort Lauderdale
- Flights from San Juan to Paris
- Flights from San Juan to Washington, D.C.
- Flights from San Juan to Hartford
- Flights from San Juan to Guadalajara
- Flights from San Juan to Minneapolis
- Flights from San Juan to Raleigh
- Flights from San Juan to Tampa
- Flights from San Juan to Boston
- Flights from San Juan to Nashville
- Flights from San Juan to Santo Domingo
- Flights from San Juan to Atlanta
- Flights from San Juan to Saint Thomas
- Flights from San Juan to Los Angeles
Flights to Chicago
- Flights from London to Chicago
- Flights from Dublin to Chicago
- Flights from Manchester to Chicago
- Flights from Toronto to Chicago
- Flights from Athens to Chicago
- Flights from Orlando to Chicago
- Flights from San Francisco to Chicago
- Flights from Hyderabad to Chicago
- Flights from New York to Chicago
- Flights from Las Vegas to Chicago
- Flights from Edinburgh to Chicago
- Flights from Denver to Chicago
- Flights from Bangkok to Chicago
- Flights from Minneapolis to Chicago
- Flights from Riga to Chicago
- Flights from Glasgow to Chicago
- Flights from Austin to Chicago
- Flights from Edmonton to Chicago
- Flights from Tallinn to Chicago
- Flights from Paris to Chicago
Popular routes
- Flights from Cork to Tel Aviv
- Flights from Cairo to Athens
- Flights from Quito to Bogotá
- Flights from London to Milan
- Flights from Nairobi to Zanzibar
- Flights from Townsville to Gold Coast
- Flights from Paris to Nottingham
- Flights from Curitiba to Dublin
- Flights from San José to Panama
- Flights from London to Faro
- Flights from Thessaloniki to Zagreb
- Flights from Kyiv to Rhodes
