Book cheap flights from Boston to Chicago from £26

Last minute flights from Boston to Chicago

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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.

Boston Chicago

BEST

DEAL

Sun, 08 Dec BOS - ORD

Mon, 09 Dec ORD - BOS

-11 %

£127 £114

Prime price per passenger

Boston Chicago

BEST

DEAL

Tue, 03 Dec BOS - ORD

£27 £26

Prime price per passenger

Boston Chicago

BEST

DEAL

Tue, 03 Dec BOS - ORD

Tue, 03 Dec ORD - BOS

-11 %

£62 £55

Prime price per passenger

Boston Chicago

BEST

DEAL

Sat, 23 Nov BOS - ORD

Sun, 01 Dec ORD - BOS

£273 £268

Prime price per passenger

Boston Chicago

BEST

DEAL

Wed, 18 Dec BOS - MDW

Thu, 19 Dec MDW - BOS

£106 £98

Prime price per passenger

Route information

Distance: 854 miles

Boston airports

Logan International Airport (BOS) How far from city centre: 3 miles

Chicago airports

O'hare International Airport (ORD) How far from city centre: 14 miles

Midway Airport (MDW) How far from city centre: 4 miles

Searching for Boston to Chicago flights?

Flights from Boston to Chicago

Have you been dreaming lately about setting off to your dream destination in United States? If you’ve been planning a trip away from Boston, or if you're looking for inspiration and ideas to travel to Chicago, in eDreams we’ve got you covered. We have amazing flight deals for your flight from Boston to Chicago!

Keep reading and find out everything you need to know before your trip, together with the best tips and tricks to find the best deals and to book your flight in the easiest and most comfortable way. Our essential information and expert tips will help ensure your travels in United States are as smooth as possible.

Choosing eDreams means selecting a travel companion that simplifies the art of trip planning. Get your booking today with Europe’s largest travel agency and let us help you prepare for your next adventure at the lowest price.

Tips to find cheap flights

In eDreams, we always provide the best deals for your flight to Chicago (CHI) from Boston (BOS). To make sure you secure the best prices, you can also follow these easy steps. Check them out and start saving money while still keeping the same level of comfort.

Here are five tips to help you find low-cost flights to Chicago :

Book early: although some travellers wait until the last minute to find potential discounts, we always recommend purchasing your flight tickets in advance. This will increase your chances of securing lower prices and avoiding higher costs later on.
Compare all airlines: in eDreams, you can find a variety of airlines offering flights between Boston and Chicago. Once our search engine shows you the available options for this route, compare fares from both budget and traditional airlines. Being flexible with your travel dates can also help you find the best deals.
Choose the cheapest days to make your booking: the most affordable days to find cheap flights from Boston are typically between Tuesday and Thursday. Weekend flights and peak season travel usually come with higher prices, so consider midweek or off-season travel to save more.
Explore city break deals: if you plan to stay in a hotel, check out our city break offers from Boston. And if you plan to hire a car in United States, eDreams can offer great discounts on your total package.
Take advantage of eDreams Prime deals: by becoming a member of eDreams Prime, you'll access great deals on flights, hotels, and car hire all year round, with the added benefit of travelling with more flexibility and peace of mind.

Airlines flying from Boston airport to Chicago airport

Through eDreams you can book regular flights on this route, and you’ll typically get access to various service types, from economy to premium, to suit different budgets and preferences. To further enhance your journey, consider also the following tips:

Use noise-cancelling headphones: they can help create a more peaceful environment, which will make your flight more comfortable.
Drink plenty of water: cabin air can be particularly dry, so make sure you stay hydrated throughout the flight.
Choose your seat wisely: think about legroom and proximity to amenities onboard. For example, if you’re travelling with children, booking a seat near the lavatories might be a good idea.
Stretch regularly: get up and move around to improve your leg circulation during the flight.

How long does a flight from Boston to Chicago last

The duration of a flight from Boston to Chicago depends on factors like the specific flight path, weather, and any layovers. Typically, direct flights are quicker, while flights with stopovers may take more time. At eDreams, we provide up-to-date flight details, helping you find the best travel options. You can easily compare flight times from Boston to Chicago on our platform to ensure you have the most accurate and convenient information for your journey.

Airports in Boston and Chicago

Boston aiport facilities

The Boston airport offers a wide range of amenities to enjoy before your flight, from high-end shopping to gourmet dining. Grab some last-minute souvenirs, pick up a bestseller for the flight, work on your laptop using the free Wi-Fi, or indulge in a nice meal before you take off.

Chicago airport facilities

After collecting your luggage at Chicago airport, ensure you have an internet connection on your phone before leaving. If you need a local SIM card, it's easier to find a store at the airport, though it might be a bit pricier.

Besides this, check also your transportation options from Chicago airport to your accommodation, whether it’s a taxi, public transport, or a pre-booked shuttle. Chicago airport staff will be able to assist with the best options at the information desk.

Booking a flight from Boston to Chicago

Booking your flight through eDreams is simple. Just enter Boston and Chicago as your departure and destination cities, choose the dates of your trip, and search through the available options. Our search engine will find the best deals from thousands of routes and flight combinations.

We also offer a ‘Smart Choice’ option, by which we highlight the most competitive flights at the top of the search results. You can also apply filters to view only flights to Chicago from your preferred airlines.

Changes to the price of your flights during your booking

Flight fares are set up using a complex pricing algorithm based on demand and seat availability. As a result, the cost of your flight may vary during your booking process. To secure the best price for your flight to Chicago, make sure you book as soon as you find a flight ticket that suits your pocket.

eDreams Prime members discounts

As an eDreams Prime member, you can access exclusive deals and save hundreds on flights, hotels, and car hires, along with many other benefits. Join the world’s largest travel membership community and discover all the advantages of eDreams Prime.

Last-minute bookings with eDreams

eDreams also offers last-minute flights at competitive prices. While these may be more expensive, we provide a range of options to suit your needs. Keep in mind, though, that last-minute prices can be higher, particularly during peak travel season. Being flexible with your travel dates can increase your chances of finding better deals.

Checking in before your flight

Online check-in usually opens 24 to 48 hours before the departure time. Once your booking with eDreams is completed, we’ll email you one week before your day of departure with instructions on how to check in for your flight.

Best season to travel from Boston to Chicago

United States offers endless possibilities, from its rich gastronomy to its diverse culture and stunning nature. The best time to travel depends on your preferences and availability. Always consider the climate, peak tourist season, and the type of experience you’re seeking.

Expect larger crowds during peak season, but you'll also enjoy a lively atmosphere and more cultural and touristic offerings. Travelling off-season usually means fewer crowds, lower prices on flights and accommodations, and a more authentic glimpse into local life. While some outdoor activities may be limited due to the weather conditions, popular attractions will likely be less crowded, allowing for a more immersive experience.

Chicago weather

The weather in Chicago can change depending on the season, so it's a good idea to check the forecast before traveling from Boston. Whether you encounter cooler or milder temperatures, being aware of the local climate will help you plan your trip and pack accordingly. Since weather can influence your experience and activities in Chicago, staying informed will ensure you're prepared to make the most of your visit.

Things to do in Chicago

Explore the vibrant spirit of Chicago with a variety of activities for every everyone to enjoy. From its iconic landmarks to its rich history, every traveller will find something to enjoy there.

Dive into the city's history and culture by visiting famous landmarks and museums, and indulge in United States's diverse cuisine. For those who prefer outdoor activities, visiting some of the stunning natural landscapes of Chicago is a must. The city has something to offer for everyone, whether you’re travelling by yourself, as a couple, or with your family.

How many days you should plan to you visit Chicago

To fully experience Chicago, 3 to 7 days should give you enough time. With that amount of time at your disposal, you should be able to explore major attractions and soak in the city’s atmosphere without rushing. If you have more time, you can always dive deeper into the most authentic neighbourhoods, savour the culinary scene, and relax by walking around its pedestrian areas.

Car hire to move around United States

Hiring a car in Chicago can be a great option, as it will give you the freedom to explore the regions beyond the metropolitan areas at your own pace. Tailor your itinerary to your schedule and budget, especially if you plan to stay in the country for more than a week.

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

Find the best flight deals on eDreams. Complete your booking by selecting your travel dates, choosing a hotel, and finding a great car hire deal. Don’t wait—book your cheap flight from Boston to Chicago today!

At eDreams, we provide all the information you need for more than 155,000 flight routes, 690 airlines, 2,100,000 hotels worldwide, and 40,000 destinations. Our wide range of holiday packages will help you save significantly on your next trip.

Don’t miss out on this opportunity to get a great deal for your next trip—book your flight now!

FAQs about flights from Boston to Chicago

What are the advantages of purchasing flexible flight tickets to Chicago through eDreams UK?

With a flexible flight ticket, you're assured a refund or the option to rebook without any additional fees if your flight from Boston to Chicago gets canceled. eDreams UK has got you covered, ensuring peace of mind and hassle-free travel changes! Plus, this flexibility allows you to adapt your travel plans with ease, offering greater convenience in today’s unpredictable travel environment.

How can I search for and book flights from Boston to Chicago on eDreams UK, and also find the best deals?

With our flight search engine, you can discover flights starting at just £26 for the route from Boston to Chicago. At eDreams UK, our priority is to offer you the most affordable options. You have the flexibility to customize your search based on various criteria, including stopovers, airports, travel dates, and additional filters. This way, you can tailor your journey to meet your specific needs and preferences, ensuring a seamless travel experience.

When is the best time to book a flight ticket from Boston to Chicago?

The top months for booking flights from Boston to Chicago are May, June and March. Travelers often find the best deals and optimal flight options during these times, making them ideal for planning your trip.

What are the best months to book a flight from Boston to Chicago?

The best time to fly to Chicago from Boston really hinges on various personal preferences, particularly regarding budget considerations. In terms of popularity, June stands out as the top month for flights to Chicago from Boston, as indicated by our customer search data. Following closely are August and May. If your goal is to escape the hustle and bustle of peak season and find a more tranquil experience, consider traveling during January, March or December. These months are associated with significantly fewer searches, making them a great choice for those seeking a quieter getaway from Boston to Chicago.

How long does it take to fly from Boston to Chicago?

The average flight time from Boston to Chicago is approximately 02:54 hours. This journey typically covers a distance of about 1,391 km. Please note that the flights along this route may include one or more layovers in different cities.

What airports offer flights from Boston to Chicago?

Travelers flying from Boston to Chicago typically depart from Logan International Airport (BOS) to O hare International Airport (ORD). This popular route is served by several airlines, offering a range of options for passengers. The airlines operating flights on this route include: United Airlines, American Airlines and Spirit Airlines. American Airlines. Spirit Airlines.

The airlines that operate indirect flights between Boston and Chicago include:

The flight provided by Spirit Airlines has a scheduled layover in Baltimore, MD. Please note that this stop will last for a minimum of 379 minutes. Make sure to plan accordingly for this connection!

Flight Time 2 h and 54 m Flights from Boston and Chicago last around 2 h and 54 m, although this flight time may also depend on other factors.

Cheapest flight £26 The cheapest price available for flights from Boston to Chicago that have been booked by our customers in the last 72 hours

Airport of Departure Logan International Airport You will depart from Logan International Airport when flying from Boston to Chicago

Airport of Arrival O'hare International Airport Outbound flights from Boston to Chicago arrive at O'hare International Airport