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✅ Book flights tickets by phone. This is a great service as it is extremely time-saving and helpful for the people who are busy.

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Flight tip

Ask about seats at the gate. If you were unable to secure good seats before departure it is always worth trying at check-in or the gate. Passengers do cancel and if the flight is not full the agent may be able to find you a better option- such as an aisle/window combo for a couple. This gives you a good chance of getting all three seats in a row if the flight is not at full capacity. Even if someone does show up to claim the middle seat they will probably be happy to swap to let you sit together.

MY FIRST EVER TRIP REPORT - UNITED B737-800 - Chicago (ORD) - Boston (BOS)

Explore More Boston to Washington.

The flight time from Boston to Chicago is 2 hours, 46 minutes. The time spent in the air is 2 hours, 16 minutes.

The flight distance from Boston to Chicago is Miles. Non-stop flight time from Boston to Chicago is around 3 hours 15 minutes. Fastest one-stop flight between Boston and Chicago takes close to 5 hours.

The fastest direct flight from Boston to Chicago takes 2 hours and 41 minutes. The flight distance between Boston and Chicago is miles (or 1, km).

Frequently asked questions - FAQ.

United Airlines currently holds the fastest travel time with two hours and 39 minutes. The total flight duration time from Boston (BOS) to Chicago (MDW) is typically 8 hours 05 minutes. This is the average non-stop flight time based upon historical flights for this route.

If the weather is good and all goes as scheduled, you could be flying into Chicago, IL (ORD-O'Hare Intl.) from Boston, MA (BOS-Logan Intl.) in only 2 hours and 40 minutes.