Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Chicago to Boston

Flexible with dates? We find the best price for the week of the day you select *Prices may vary after you search.

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week: Jun 23 - Jun 29

Flights from just €58

€58

€77

€100

€94

€98

€144

€93

€87

€98

€95

€275

€100

JuneJulyAugustSeptember

Route information

Exchange rate

1 EUR = 1.17 USD

1 USD = 0.86 EUR

Last revised on Fri, 06/20

Distance: 1375 kms

Chicago airports

O'hare International Airport (ORD)How far from city centre: 22 kms

Midway Airport (MDW)How far from city centre: 6 kms

Boston airports

Logan International Airport (BOS)How far from city centre: 5 kms

Your getaway from Chicago to Boston

Dreaming of a getaway to United States? Look no further! Whether you're departing from Chicago or seeking inspiration for your next adventure, eDreams has you covered. Discover incredible flight deals from Chicago to Boston

Let our team of travel experts guide you through every step of your planning process. From choosing the ideal accommodations to discovering hidden gems off the beaten path, we'll provide personalised recommendations to ensure your trip is truly unforgettable.

Don't let your dream holiday remain just a dream. Visit eDreams, Europe’s largest travel agency, and explore our wide range of flight deals to Boston. With our affordable prices, expert advice, and exceptional customer service, we're your partner in creating unforgettable memories. Start Planning Your Adventure Today!

Tips to find cheap flights

At eDreams, we're dedicated to providing you with the best deals on your flight to Boston (BOS) from Chicago (CHI). To help you secure the low-cost fares, follow these simple tips:

1. Book early and be flexible: While last-minute deals can sometimes be found, booking your flight well in advance generally leads to lower prices. Consider being flexible with your travel dates to maximise your savings potential.
2. Choose the right days to book: Typically, Tuesdays and Thursdays are the most budget-friendly days to book flights from Chicago. Avoid weekends and peak travel seasons to save more and find your cheap flights to Boston.
3. Bundle your trip for extra savings: If you're planning to stay in a hotel or rent a car in Boston, consider our city break deals and car hire discounts for additional savings.
4. Join eDreams Prime for exclusive benefits: As an eDreams Prime member, you'll enjoy year-round discounts on flights, hotels, and car hire, along with flexible booking options and added peace of mind.

By following these tips, you can significantly reduce the cost of your trip to Boston and enjoy a more affordable holiday.

Airlines flying from Chicago to Boston

Choose from TOP airlines and various service types, including economy, premium economy, business class, and first class, to find the perfect option for your needs and budget.

Enhance your flight experience

To make your journey as comfortable as possible, consider the following tips:

Prioritise noise Cancellation: Invest in a good pair of noise-cancelling headphones to create a more peaceful and relaxing environment.
Stay hydrated: Cabin air can be quite dry, so drink plenty of water throughout the flight to avoid dehydration.
Choose your seat strategically: Consider factors like legroom, proximity to amenities, and your travel companions when selecting your seat. For example, families with children may prefer seats near the lavatories.
Move around regularly: Get up and stretch your legs periodically to improve blood circulation and prevent discomfort.

Arrive in Boston feeling rested and ready to embark on your next adventure. Follow these tips for a more enjoyable flight experience.

How long does a flight from Chicago to Boston last

The distance between Chicago and Boston may vary depending on the flight type. You will reach your destination faster with a direct flight, but it’s sometimes cheaper if you choose the multi city flight option.

To ensure a comfortable journey, pack essentials like comfy clothing and travel pillows. Don't forget to bring entertainment, such as books or downloaded movies, to pass the time.

Airports in Chicago and Boston

Chicago Airport facilities

In Chicago airports you can enjoy a wide range of amenities, including upscale shopping, gourmet dining, free Wi-Fi, and comfortable workspaces.

Boston Airport facilities

In Boston, once you collect your luggage, ensure your phone has an internet connection. Consider purchasing a local SIM card at the airport for convenient connectivity.

Transportation options

Plan your transportation from Boston to your accommodation in advance. Choose from taxis, public transport, or pre-booked shuttles. The airport staff at Boston can assist you with the best options.

Booking a flight from Chicago (CHI) to Boston (BOS)

Booking your flight with eDreams is a breeze. Simply enter Chicago and Boston as your departure and destination cities, select your desired travel dates, and explore the available options. Our powerful search engine will uncover the best deals from countless routes and flight combinations.

We also offer the 'Smart Choice' feature, which highlights the most competitive flights at the top of the search results.

Changes to the price of your flights during your booking

Flight fares are determined by a sophisticated pricing algorithm that considers demand and seat availability. Consequently, the price of your flight may fluctuate during the booking process. To secure the best possible fare for your flight to Boston, be sure to book as soon as you find a ticket that aligns with your budget.

eDreams Prime member discounts

As an eDreams Prime member, you can enjoy exclusive deals and save significantly on flights, hotels, and car rentals, along with numerous other benefits. Join the world's largest travel membership community and discover the advantages of eDreams Prime.

Last-Minute bookings with eDreams

eDreams also offers competitive prices for last-minute flights. While these may be more expensive, we provide various options to suit your needs. Keep in mind that last-minute prices can be higher, especially during peak travel season in United States. Flexibility with your travel dates can increase your chances of finding better deals.

Checking in before your flight

For flights with almost every airline, online check-in typically opens 24 to 48 hours before departure. Upon completing your booking with eDreams, we'll email you a week before your flight, providing detailed instructions on how to check in.

Best season to travel from Chicago to Boston

United States offers a wealth of experiences, from its delectable cuisine to its vibrant culture and breathtaking natural beauty. The ideal time to travel depends on your personal preferences and availability. Consider factors such as the climate, peak tourist season, and the type of experience you desire.

During peak season, expect larger crowds but also a more lively atmosphere and a wider range of cultural and tourist activities. Travelling off-season often translates to fewer crowds, lower flight and accommodation prices, and a more authentic taste of local life. While some outdoor activities may be limited due to weather conditions, popular attractions are likely to be less crowded, allowing for a more immersive experience.

Boston weather

The weather in Boston varies by season. Always check the weather info, and pack accordingly, and don't forget to bring an umbrella—some offer UV protection for sunny days!

Things to do in Boston

Discover the essence of Boston with a wide range of activities to suit all tastes. From its iconic landmarks to its cultural treasures, there's something for everyone to explore.

Immerse yourself in the city's history and culture by visiting renowned museums and historical sites. Savour the flavours of United States with its diverse culinary scene. For outdoor enthusiasts, United States's stunning natural landscapes offer endless opportunities for adventure. Whether you're travelling solo, as a couple, or with family, Boston has something to offer everyone.

How many days should you plan to visit Boston?

To truly experience Boston, a stay of 3 to 7 days is recommended. This allows you to explore the city's major attractions and soak up its vibrant atmosphere without feeling rushed. If you have more time, delve deeper into the city's authentic neighbourhoods, savour its culinary delights, and unwind by strolling through its pedestrian areas.

Hiring a car to move around United States?

Hiring a car in Boston can be a convenient option, granting you the freedom to explore the surrounding regions at your own pace. This is especially beneficial if you plan to stay in the country for more than a week. Customise your itinerary to suit your schedule and budget, and discover the hidden gems that lie beyond the city centre.

Book your flight now from Chicago to Boston at a lower price

Discover incredible flight deals starting at just 46 on eDreams. Complete your booking by selecting your travel dates, choosing a hotel, and finding a great car hire deal. Don't miss out on this opportunity to save on your next trip and book your cheap flight now!

Experience the eDreams difference

With over 155,000 flight routes, 690 airlines, 2,100,000 hotels worldwide, and 40,000 destinations, eDreams offers a vast selection of holiday packages to suit your needs. Our commitment to providing exceptional value and customer service ensures that you'll find the perfect deal for your next adventure.

Frequently asked questions about flights from Chicago to Boston

What are the benefits of booking flexible flight tickets?

Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. At eDreams have you covered!

For flights from Chicago to Boston, how can I find the cheapest price?

On eDreams we use machine learning to find the most economical flight between Chicago and Boston. By taking into account the combinations of airlines, stopovers, direct flights as well as the various criteria for the journeys, our search engine allows us to offer our customers the best price under the best conditions.

When booking, when is the best time to do so in order to get the best prices for Chicago to Boston flights?

The most popular month for flights from Chicago to Boston are: April, May and July.

When is the best time to travel from Chicago to Boston?

A good period of the year to visit Boston from Chicago really depends on lots of personal preferences, price being one of the main criteria When it comes to popularity, June is the best month to fly to Boston from Chicago, basedd on searches from our customers, followed by August and July. If you prefer to avoid the busy season and get away from the crowds February, December and March are the months with fewer searches for the route Chicago - Boston.

What is the duration of a flight from Chicago to Boston?

Flight time, on average, from Chicago to Boston is usually 02:27 hours on average, at an average distance of 1,394 km, for flights for the route (which may have 1 or more stops in other cities in between).

Which airports have flights between Chicago and Boston?

The most common route form Chicago to Boston is: O'hare International Airport (ORD) to Logan International Airport (BOS). These airlines fly this route:

American Airlines.

What airlines fly from Chicago to Boston?

Airlines that have direct flight routes from Chicago to Boston are:

United Airlines.
American Airlines.
Spirit Airlines.

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