Looking for a trip in July or another month? idealo has the information you need to find the perfect flight from Nashville to Chicago. A quick search through the database shows that tickets start at a reasonable $107. Flights on Mondays and Saturdays are up to 12 % more expensive when compared to other days of the week. United Airlines is chosen most of the time by idealo customers, making it the most frequently used airline for this connection. Find a direct flight to Chicago every day with either American Airlines or United Airlines. With prices starting from $107 per ticket for a direct flight, this is the most affordable offer in our database. The most affordable prices for flights with stopovers start at $112 and for direct flights at as little as $107. Only 15 % of users opt for stopover flights, while 68 % choose direct flights. Concerning stopover flights idealo users choose stops in Charlotte or Dallas most often. The fastest stopover flight lands in Charlotte and has a flight duration of 4 hours and 26 minutes. This flight takes only 3 hours and one minute longer than a direct flight. Whether you want to fly with American Airlines or another airline – let us help you get the best deal on offer.