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Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from San Juan to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A non-stop flight is the most convenient and comfortable way to fly from San Juan to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
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.
The cost of a one-way flight from San Juan to Chicago ranges from $106 (July 2026) to $255 (November 2026). On average, the ticket price is about $136–$154.
Ticket prices for San Juan — Chicago follow a predictable curve: rise, peak, and decline. This typical seasonal pattern lets you plan your purchase to avoid overpaying.
Prices rise from May 2026 to June 2026 (+14%), then decline from June 2026 to July 2026 (22%). The cheapest tickets are in June 2026–July 2026 (averaging $121), while the priciest are in July 2026–November 2026 ($180).
For savings, plan your flight for June 2026–July 2026 — you could save up to 33%. Try to avoid July 2026–November 2026 when possible: prices are at their highest then.
Price spread on this route is 38.3%. Costs depend heavily on the season, so flexibility in choosing your departure month is especially valuable here.
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San Juan — Chicago
05/10/2026
Departure
Direct flight
UA2089
starting at $430
San Juan — Chicago
05/23/2026
Departure
Direct flight
WN1093
starting at $153
San Juan — Chicago
06/03/2026
Departure
Direct flight
AA2592
starting at $400
San Juan — Chicago
06/22/2026
Departure
Direct flight
UA2088
starting at $366
San Juan — Chicago
07/26/2026
Departure
Direct flight
F93345
starting at $319
San Juan — Chicago
07/29/2026
Departure
Direct flight
F93345
starting at $183
San Juan — Chicago
11/25/2026
Departure
Direct flight
UA2088
starting at $336
starting at $336
starting at $153
starting at $136
starting at $106
More than 4 airlines operate flights from San Juan to Chicago, including United Airlines, Southwest Airlines, American Airlines, and Frontier Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $106, 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.
The cheapest flight ticket from San Juan to Chicago according to data for the last 48 hours costs $106
Often the best time to buy tickets from San Juan to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from San Juan to Chicago can be found flying in these months: July, May, June.
The fastest flights from San Juan to Chicago start from 5 hours 13 minutes in the air.
The following airlines operate direct flights on the route San Juan — Chicago: United Airlines, Southwest Airlines, American Airlines
The cheapest one-way flight from San Juan to Chicago departs on 07/29/2026, is operated by Frontier Airlines and costs $106
The cheapest roundtrip flight from San Juan to Chicago departs on 06/03/2026, is operated by American Airlines and costs $234
Fastest flight from San Juan to Chicago takes 5h 13m
There are direct flights on this route 4 days a week: Su, Mo, We, and Sa
The distance between San Juan and Chicago is 3305km (2049 miles). The time difference between San Juan and Chicago is 2h
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.
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