Cheap Flights from Chicago to San Juan from CAD 63️ 2024

App

Help

CAD

Search Bookings

Flights from Chicago to San Juan

Hotels in San Juan

Worldwide Coverage

Flights to over 5,000 cities

One-stop Service Guarantee

Price guaranteed upon confirmed payment, booking guaranteed once tickets issued

Secure Payment

Convenient & reliable booking and payment system

Find Chicago to San Juan flights starting at CAD 63.

Book one-way or return flights from Chicago to San Juan from as little as CAD 63. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Chicago to San Juan? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to San Juan. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Chicago to San Juan

View airlines operating flights from Chicago to San Juan. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines

From CAD 76

Spirit Airlines

From CAD 76

Southwest Airlines

From CAD 143

Delta Air Lines

From CAD 196

United Airlines

From CAD 205

Sun Country Airlines

From CAD 206

Jetblue Airways

From CAD 229

Allegiant Air

From CAD 247

American Airlines

From CAD 474

ANA airlines

Find more flights and airlines

Alternative Routes for Chicago to San Juan Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to San Juan.

Cheapest
MDW
19:13
12h 21m
1 transfer
SJU
08:34
Midway International Airport - Luis Muñoz Marín International Airport
Tue, May 7Frontier Airlines
CAD 76
ORD
07:27
10h 35m
1 transfer
SJU
19:02
O'Hare International Airport - Luis Muñoz Marín International Airport
Tue, May 7Spirit Airlines
CAD 76
RFD
18:36
20h 57m
1 transfer
SJU
16:33
Chicago Rockford International Airport - Luis Muñoz Marín International Airport
Fri, May 17Allegiant Air
CAD 247
RFD
18:36
20h 57m
1 transfer
SJU
16:33
Chicago Rockford International Airport - Luis Muñoz Marín International Airport
Fri, May 17Allegiant Air
CAD 247
Find More Flights

How do I find the cheapest flights?

When are flight tickets from Chicago (CHI) to San Juan (SJU) the cheapest?
Airlines adjust prices for flights from Chicago to San Juan based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Chicago (CHI) to San Juan (SJU) cost?
According to Trip.com's data, the lowest price is around CAD 440.
How long is the flight from Chicago (CHI) to San Juan (SJU)?
It takes about 4 hours 44 minutes to fly from Chicago (CHI) to San Juan (SJU).
What is the transportation method from the main airport to downtown in San Juan?
- The distance from Luis Muñoz Marín International Airport to downtown is about 11km, by taxi about 30 minutes.
What are the most popular airlines that fly from Chicago (CHI) to San Juan (SJU)?
Airlines with flights from Chicago (CHI) to San Juan (SJU): United Airlines, Air New Zealand, Alaska Airlines, American Airlines, Southwest Airlines, Spirit Airlines and Air Canada.
What's the most popular airline for direct flights from Chicago (CHI) to San Juan (SJU)?
United Airlines operates 1 direct flights from Chicago (CHI) to San Juan (SJU).
How many airports in San Juan (SJU)?
There are 2 airport(s) in San Juan (SJU): Fernando Luis Ribas Dominicci Airport and Luis Muñoz Marín International Airport.

How to find a cheap flight from Chicago to San Juan

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to San Juan. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information for Chicago to San Juan Flights

Cheapest direct flight price	CAD 62
Cheapest return ticket price	CAD 169
Cheapest month	December
Peak season for travel	July
Flight distance	3,313.11km
Average flight time	4 hours 44 minutes
Popular airline	American Airlines