Cheap Flights from San Juan to Chicago Starting at $65
Helping travelers to find the best flight offers
Cheapest flights from San Juan to Chicago
Fly from San Juan to Chicago with confidence — our search scans more than 700 airlines, over 50 travel agencies and 5+ top booking systems to uncover the best prices, convenient schedules and flexible booking conditions. Compare options in seconds and lock in your ideal Puerto Rico to Illinois itinerary with ease.
Remember that on average the ideal time to book flights is 2 months before departure!
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from San Juan to Chicago
Airlines operating on route
Direct Flights from San Juan to Chicago
Fly nonstop from San Juan to Chicago for the fastest, most convenient way to bridge the Caribbean and the Midwest—less time in transit means more time exploring the Windy City. While connecting options can sometimes be cheaper, a direct flight saves hours and hassle, giving you a smoother, more comfortable travel day.
Schedule of direct flights from San Juan to Chicago
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from San Juan to Chicago:
San Juan airports overview
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Chicago airports overview
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Frequently asked questions (FAQ)
Answers to questions about the route that travelers are most interested in.
Special offers and sales on air tickets from San Juan to Chicago
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Alternative routes
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Cheapest one way flight
$65
JetBlue Airways
1 transfer
7h 56m
06/03/2026
The cheapest one-way flight from San Juan to Chicago departs on 06/03/2026, is operated by JetBlue Airways and costs $65
Cheapest round trip flight
$108
JetBlue Airways
1 transfer
18h 25m
09/05/2026
The cheapest roundtrip flight from San Juan to Chicago departs on 09/05/2026, is operated by JetBlue Airways and costs $108
The fastest flight
5h 11m
Fastest flight from San Juan to Chicago takes 5h 11m
Direct flights
Several times a week
There are direct flights on this route 2 days a week: Mo and Th
Earliest flight
7:10 AM
Latest flight
4:52 PM
Direct flights count
25
Distance
3305km
Timezone difference
2h
The distance between San Juan and Chicago is 3305km (2049 miles). There are 25 direct flights from San Juan to Chicago. The time difference between San Juan and Chicago is 2h. Flights from San Juan begin at 7:10 AM. The latest flight from San Juan departs at 4:52 PM
Avg Price
More than 5 airlines operate flights from San Juan to Chicago, including Spirit Airlines, United Airlines, American Airlines, JetBlue Airways, and Frontier Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $65, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.
Luis Muñoz Marín International Airport (SJU) is Puerto Rico’s main international gateway and typically handles most long-haul and regional flights, with legacy carriers and low-cost airlines operating side by side. The airport sits about 8 miles (roughly 20–30 minutes) east of San Juan’s Old San Juan and Condado neighborhoods; taxis and app-based rides cost commonly in a moderate range, while public buses and shared shuttles can be cheaper but slower. Ground transportation includes rental cars, private shuttles, and occasional hotel transfers, with journey times varying by traffic. Pros: convenient for international connections and city access; cons: can be busy during peak travel periods and may involve longer lines for security and customs.
How much is the cheapest flight ticket from San Juan to Chicago?
The cheapest flight ticket from San Juan to Chicago according to data for the last 48 hours costs $65
When is the best time to buy air tickets on the route San Juan — Chicago?
Often the best time to buy tickets from San Juan to Chicago is 2 months before departure.
How long does it take to fly from San Juan to Chicago?
The fastest flights from San Juan to Chicago start from 5 hours 11 minutes in the air.
Which airline can fly direct from San Juan to Chicago?
The following airlines operate direct flights on the route San Juan — Chicago: Spirit Airlines, United Airlines, American Airlines
Chicago is served mainly by two airports: O’Hare International (ORD) and Midway (MDW). O’Hare is the city’s primary international hub, handling many long-haul and connecting flights with a strong presence of legacy carriers and global alliances; fares can be mid-to-high depending on season and routing. It sits about 17–20 miles northwest of downtown; transit options include the CTA Blue Line (roughly 45–60 minutes), taxis and rideshares (30–60 minutes, variable tolls), and airport shuttles. Pros: extensive route network and frequent services; cons: large terminals and possible busy peak-time crowds. Midway functions as a budget-leaning domestic alternative with a heavier low-cost carrier profile and generally more affordable fares. Located some 10 miles southwest of downtown, Midway is reachable by the CTA Orange Line (about 25–35 minutes), taxis/rideshares (20–40 minutes), and local buses. Pros: smaller footprint and quicker check-in/walk times; cons: fewer international connections and limited late-night options compared with O’Hare.
We couldn't find any special offers for flights from San Juan to Chicago
