Many airlines offer flexible change policies
The lowest prices found within the past 7 days from Chicago to Boston were for one-way flights and £639 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.
|Origin Airport IATA code||MDW|
|Destination Airport IATA code||MHT|
|Number Of Flight Options||1|
|Average Flight Time||3 hours 17 mins|
|Origin Airport IATA Code||CHI|
|Destination Airport IATA Code||BOS|
|Number of Airlines Serving||17|
|Direct Flight Time||2 15|
Stay informed about current flying restrictions or health advisories by checking our Covid-19 Travel Advisor. This is the page to visit for all recent developments for your Chicago to Boston flight.
Firstly, you need to consider whether you want to fly the O'Hare Airport to Logan Intl. Airport route or the Chicago, IL Airport (ORD-O'Hare Intl.) to Manchester Airport route between Chicago and Boston. Secondly, decide on who you want to travel with. American Airlines is one of the 2 carriers that service the first route. One the second flight path, American Airlines is among the 1 airlines you can choose from.
If you're the kind of traveller who likes chatting to their seat mate, you'll have an average of 2 hours and 26 minutes to do so during your nonstop Chicago to Boston flight. This journey of 870 miles can sometimes pass by in 2 hours and 13 minutes, which still gives you time to make a new friend or two.
As an Ebookers customer, you may be eligible for a no-change-fee cancellation for your Boston booking and a credit that you can use for another flight. Your account is the place to go to see if your reservation has this flexibility. If you have any more questions, our Customer Service Portal is here to help.
The most popular flight routes between Chicago and Boston are:
Get your long-awaited holiday off to the best start possible. With a good number of airlines flying between Chicago and Boston, you'll find one that will enable you to do just that among these popular options:
Spur-of-the-moment holidays can be lots of fun. With approximately 12 flights operating from Chicago to Boston each day, you'll be able to choose the time that works for you.
Getting to your destination comfortably and confidently is as important as having a great holiday once you get there. Take the stress out of flying by choosing JetBlue, Delta or American Airlines. They all employ social distancing rules and have COVID-19 measures in place, which may be capped capacity flights and keeping the middle seat empty.
This is one is easy to remember: Flight Fridays. We found that tickets booked on a Friday resulted in the best deal on average in 2020. However, Wednesdays can be the worst days to purchase plane tickets, as it was the day with the highest average ticket price based on flight demand on ebookers in 2020.
When analysing flight demand on ebookers in 2020, Monday turned out to be the cheapest day to fly. That's definitely something to consider when booking your next trip! Weekends may seem like the most logical time to start your holiday, but airline tickets were on average more expensive for flights departing on Saturdays, so keep this in mind when planning for your next trip.
*According to flight demand on ebookers.com from January to December 2020. Savings are subject to change and may vary depending on selections made.
Our advanced search tools and comprehensive filters help you find a flight that fits your budget. To search for cheap flights, just enter your travel dates and sort your results by price. With all available tickets listed lowest price first, it’s easy to select the one that’s easiest on your wallet.
To find the cheapest flights from Chicago to Boston, you can also travel outside peak season. The more flexible you can be on travel dates, the easier it is to find those cheap flight tickets. We know, for example, that the cheapest time to travel between Chicago to Boston is February. In the current list of deals available, prices start at £639 and can rise to £700 for return flights.
Every day between Chicago and Boston, 42 flights from 17 airlines jet back and forth. And with ebookers, you can book tickets for any one of those flights. If you book a direct flight with American Airlines, KLM, Qatar Airways, JAL, Azul, Icelandair, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, JetBlue Airways, Royal Jordanian, Hawaiian Airlines, Iberia, ANA, British Airways, you’ll arrive safely in your destination in around 2hours. If you can think of a quicker way to cover the 1389 km between null and null, let us know!
We only need a little information to give you a lot of choice. Just tell us when you’re planning your family holiday, long weekend, luxury getaway or quick business trip, and we’ll do the rest. And to keep your choice-making easy, we’ve given you plenty of ways to narrow down your search. Choose one-way, roundtrip or multi city flights, select your preferred airline, your time of arrival and departure and cabin class using the filters.
Once you’ve told us what you want, we’ll show you what’s on offer. All you need to do is take your pick and start packing.
We want the experience of booking your flight from Chicago to Boston to be as simple as possible. That’s why we designed our search and filter options to make your life easy. Whether you are travelling on business or for pleasure, ebookers has you covered.
When you’re ready to book, our service is always fast and transparent. We know plans change, so we have a range of flexible booking options. Choose between refundable bookings and flights with no charges should you need to rearrange and travel stress-free.
Reviewed on 29 Sep 2019
Reviewed on 4 Dec 2019
Reviewed on 7 Dec 2021
Reviewed on 4 Jan 2020
Reviewed on 23 Aug 2021
*Savings based on all holiday package bookings with Flight + Hotel on ebookers.com from January 2017 to December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.
Fare, taxes & fees: Fares were found on ebookers.com and are updated daily. They include all taxes and fees, except baggage fees.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a £25.00 / 45.00 Euro service fee charged by ebookers, plus any airline fare and tax increase that may be applicable.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.