Flights from Chicago (ORD) to Boston (BOS)

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For domestic flights, we recommend arriving at the airport in Chicago at least 2 hours before your scheduled departure time. For international flights, aim to be at the airport at least 3 hours prior to ensure smooth check-in, security checks, and to account for any unexpected delays. It’s better to be early and relaxed than rushing at the last minute right? Every airline has its own rules about when check-in and baggage drop closes, so be sure to check before you head to Chicago just in case.

Timing is everything when it comes to grabbing flight tickets. Typically, it’s best to book around 4-6 weeks in advance for domestic flights and a minimum of 2-3 months for international routes. But the prices also depend on the travel demand, seasonality, and major events. You can always monitor the fare trends on Traveloka and set alerts to catch the best deals or promotions. Consider shopping around big sales events, like EOFY, Black Friday or Boxing Day to get the best deal.

Looking for the best deals to Boston? Historically, midweek flights (particularly on Tuesdays and Wednesdays), tend to be cheaper on just about every route, including Chicago to Boston, due to lower demand. However, airfares can fluctuate so we recommend keeping an eye on flight prices and being flexible with your travel dates. Booking in advance can be one the hacks to travel to Boston without breaking the bank! It's easy to compare dates when booking flights form Chicago with Traveloka, too. We automatically show pricing for the five days following your requested date to see when the cheapest fares are available.

When booking a flight to Boston, and just about everywhere, you'll need to know the full legal name of every passenger on your booking. We also need your date of birth, nationality and passport details. It's also best to decide at the time you book your flight if you want to check a bag or choose a seat on your flight from Chicago to Boston, as it will be more expensive to add these on later or at the airport. And we're all about getting the best deal here at Traveloka!

Travelling from Chicago to Boston requires specific documents. For international flights, a passport is always necessary, this includes any domestic connections to international flights. The necessity of a visa depends on the traveller's citizenship and Boston's entry regulations. It's crucial to verify visa requirements, as rules can differ between countries. However, for domestic flights, neither a passport nor a visa is usually required, but an official ID will be needed.

Booking flight tickets with Traveloka can feel like diving into an ocean of options! Our platform provides the most comprehensive choices to ensure you find the perfect flight for your adventure. With our smooth booking process, you'll also be provided with a variety of payment methods. Anxious about transacting online? We've got you covered with our top-tier security for each transaction! With Traveloka, your flight booking journey becomes hassle-free!

When flying direct, the flight from Chicago to Boston is about 2 hours and 21 minutes.