CHI - BOS
Find cheap flights from Chicago to Boston
Good to know
|September||Best time to beat the crowds with an average 15% drop in price.|
|July||Most popular time to fly with an average 18% increase in price.|
Average price of a round-trip
|$179||(avg. price over the last 2 weeks)|
Good deal for a round-trip
When to book flights from Chicago to Boston
Top tips for finding a cheap flight
- Looking for a cheap flight? 25% of our users found flights on this route for $102 or less.
- The cheapest flight from Chicago to Boston was found 60 days before departure, on average.
- Book at least 2 weeks before departure in order to get a below-average price.
- High season is considered to be June, July and August. The cheapest month to fly is September.
- Morning departure is around 76% more expensive than an evening flight, on average*.
- If you’re looking at flights from Chicago to Boston, there are two different airports that you can fly out of. O'Hare International Airport is the largest airport in the region and harbors a high concentration of flights, while Chicago Midway International Airport is a smaller choice that is located only several miles from the city’s downtown.
- Hoping to have a direct flight from Chicago to Boston? There are several major airlines that you can choose from. Southwest Airlines is popular amongst travelers with a large amount of luggage, as they allow you to check up to two bags for free, while Delta Airlines offers many upgrade options for those who would prefer more comfortable chairs or extra legroom.
- For those that are traveling with kids, make sure to stop by one of the several children’s play areas located in Logan International Airport. These play areas are free for all travelers and feature a variety of toys, games, and activities that will help kids (and their parents) unwind after a long day of traveling.
- To help pass the time before your flight takes off from O'Hare International Airport, see if you can access one of the airport’s private lounges. American, United, and Delta Airlines all have lounges in Chicago, and they often provide complimentary or reduced price access passes for their customers.
- Flying can sometimes be stressful, so make sure you’re taking the time to unwind before boarding your plane. O'Hare International Airport has both a fitness club and a yoga room, both of which are perfect ways to let off some steam and relax before embarking on a day of traveling.
FAQs for booking Chicago to Boston flights
Which airlines have a flexible cancellation policy for flights from Chicago to Boston Logan Intl due to COVID-19?
Which airlines apply social distancing measures on flights from Chicago to Boston Logan Intl due to COVID-19?
How long does a flight from Chicago to Boston take?
How many flights are there between Chicago and Boston?
Which airlines provide the cheapest flights from Chicago to Boston?
Do I need a passport to fly between Chicago and Boston?
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Does Logan International Airport have pet relief areas?
What are good hotels near Logan International Airport?
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Does Logan International Airport have a prayer room?
How does KAYAK find such low prices on flights from Chicago to Boston?
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What is the Hacker Fare option on flights from Chicago to Boston?
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Boston?
Top 5 airlines serving Chicago to Boston Logan Intl
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