Cheap flights from Chicago to Lisbon from $239

In general, February is the cheapest month to fly from Chicago to Lisbon. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $360. If you are unable to visit Lisbon during the month of February, then departing from Chicago during the month May is also very affordable. Most momondo users find prices during this month for around $370.

Our data shows that Wednesday is the least expensive day to fly to Lisbon. Tickets to fly out on this day can be as low as $577. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Lisbon for around $790.

The cheapest time of day to fly to Lisbon is in the evening when flights can be purchased for as low as $582. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $760 on average. Flights to Lisbon from Chicago in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Chicago O'Hare Intl to Lisbon Humberto Delgado for the best Chicago - Lisbon Humberto Delgado flight prices

You are more likely to see cheaper flights to Lisbon from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Lisbon for around $787 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Lisbon from Chicago for as low as $649 on momondo.

You could potentially save up to 1% on your flight if you consider stops on a Chicago to Lisbon flight.

As of May 2026, prices for Chicago to Lisbon flights are approximately 4% more expensive when compared to flights at the same time last year.

Iberia, British Airways, and Delta are the most popular carriers operating from Chicago to Lisbon Humberto Delgado

TAP AIR PORTUGAL, United Airlines and British Airways are the top three most popular airlines that fly to Lisbon from Chicago according to our data. TAP AIR PORTUGAL is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Lisbon. Keep in mind that there are 18 different airlines that fly to Lisbon on a routine basis, so you have a few additional options to choose from.

Historically, on average around 38% of flights between Chicago and Lisbon have experienced a delay on any given week. The average delay length over the past 12 months has been 134 minutes.

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Tuesday has historically seen more delays on average compared to the rest of the week.

According to our data, TAP AIR PORTUGAL have had the least number of delays on this route over the last 12 months; with about 38% of their flights experiencing any sort of delay.

Philadelphia (PHL) was the most common stop: 14% of momondo users choosing 1-stop flights on this route connected there.

Flights via Reykjavik (KEF) offer the lowest average round-trip price of $371.

Flights connecting via Washington, D.C. (IAD) have the shortest average one-way travel time: 9h 54m.

Washington, D.C. (IAD) has the shortest average layover time for this route: 1h 29m.

As of May 2026, there are 1 flights per day flying from Chicago to Lisbon. The most common time of day flights depart is 6:00PM, with 100% of flights taking off in the evening.

As of May 2026, there are 8 flights per week flying from Chicago to Lisbon. The most common day of the week flights depart is Wed, with 25% of flights taking off on this day.