Cheap Flights from Lisbon to Chicago — $379

The Lisbon — Chicago route is served by multiple airlines, including EasyJet, Ryanair, and SATA. This is convenient for those who want the best balance of price, schedule, and travel conditions. Tickets start from $379, and depending on season and promotions, even better deals may appear. With our service, you can easily compare available options and book tickets that match your plans. The variety of carriers allows flexible choices and comfortable travel without overpaying.

Fly nonstop from Lisbon to Chicago for the fastest, most convenient way to bridge Portugal and the Windy City—perfect for maximizing your time on arrival and minimizing airport hassle. While some itineraries with connections can be cheaper, a direct flight saves hours and offers a more comfortable, stress-free start to your trip.

Lisbon Portela Airport (LIS) is the city’s main international gateway and typically handles a mix of full-service carriers and low-cost airlines, making it the prime choice for long-haul and European connections. Located about 7–8 km north of downtown, transfers to the city center can take roughly 15–25 minutes by taxi or 20–30 minutes by the Aerobus or metro; fares for public transport are usually modest while taxis can be more costly. The airport offers reasonable passenger facilities and frequent schedules, though it can get busy during peak seasons. Pros: direct links and frequent flights; cons: occasional congestion and limited late-night rail options.

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 Lisbon to Chicago

Chicago is served by multiple airports with distinct roles. O’Hare International (ORD) is the city’s primary international hub and a major transfer point for legacy carriers and global airlines; it’s typically pricier for last-minute tickets but often competitive on long-haul routes. Located about 17 miles northwest of downtown, O’Hare connects by CTA Blue Line train (roughly 45–60 minutes, modest fares), taxis and ride-shares (40–60 minutes, variable fares), plus airport shuttles. Midway (MDW) functions as a budget- and domestic-focused airport favored by low-cost carriers and some domestic legacy flights; it’s around 10 miles southwest of the Loop. Midway usually has lower fares on short-haul routes and is reachable via CTA Orange Line (around 25–35 minutes, low fare), taxis and rideshares (20–35 minutes). Pros: O’Hare provides extensive international connections and amenities, while Midway can be quicker for domestic travelers and easier to navigate. Cons: O’Hare can be crowded and involve longer transfers between terminals; Midway has fewer long-haul options and more limited international services.