Find Cheap Flights from Chicago (CHI) to Boston (BOS) from £639

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Selected flight deals from Chicago to Boston

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.

Cheap Flights from Chicago to Boston & Flight Information
Origin Airport IATA codeMDW
Destination Airport IATA codeMHT
Number Of Flight Options1
Flight Price£639
Average Flight Time3 hours 17 mins

Best Day to Book Flight from Chicago to Boston

Helpful Chicago to Boston (CHI - BOS) Flight Information

Traveling From Chicago
Origin Airport IATA Code CHI
Traveling To Boston
Destination Airport IATA Code BOS
Number of Airlines Serving 17
Available Airlines Delta
Distance 1389 km
Direct Flight Time 2 15
Flight Price £639

FAQs about flights from Chicago to Boston

Is it possible to fly from Chicago to Boston right now?

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.

Is there a direct flight between Chicago and Boston?

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.

How long is a direct flight from Chicago to Boston?

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.

Can I cancel my flight booking to Boston due to COVID-19?

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.

What are the best airports for Chicago to Boston flights?

The most popular flight routes between Chicago and Boston are:

  • Chicago, IL Airport (MDW-Midway Intl.) to Boston, MA Airport (BOS-Logan Intl.) - 82 flights per week
  • O'Hare Airport to Boston, MA Airport (BOS-Logan Intl.) - 76 flights per week
  • O'Hare Intl. Airport (ORD) to Manchester-Boston Regional Airport (MHT) - 69 flights per week
What are some of the most popular airlines flying from Chicago to Boston?

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:

  • American Airlines with 412 flights every month.
  • Delta with 369 flights every month.
  • United Airlines with 156 flights every month.
  • Allegiant Air with 34 flights every month.
How many flights are there from Chicago to Boston?

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.

Is it possible to fly on an airline that employs social distancing and other COVID-19 measures?

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.

What are the cheapest days to book a flight?

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.

What are the cheapest days to fly?

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.

Fly from Chicago to Boston with ebookers

Cheap flights from Chicago to Boston 

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.  

Find the best flight from Chicago to Boston  

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! 

Flights from Chicago to Boston — a great choice on great deals 

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.  

Book your flights with ebookers 

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. 

Need a car after flight from Chicago to Boston

Place to stay after flight from Chicago to Boston

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway, Everett, MA
The price is £210 per night from 6 Feb to 7 Feb
Situated near the airport, this luxury hotel is within 2 mi (3 km) of Encore Boston Harbor, The Freedom Trail, and Assembly Row. LEGOLAND® Discovery Center and ...
Encore Boston Harbor
Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport

2.5 out of 5
230 Lee Burbank Hwy, Revere, MA
The price is £69 per night from 30 Jan to 31 Jan
Situated near the airport, this hotel is within 6 mi (10 km) of TD Garden, New England Aquarium and Faneuil Hall Marketplace. Boston Common and Boston Convention ...
3/5 (1 review)
"Super Bar mit freundlicher Bedienung. Guter Barfood. Unvorteilhafter Frühstücksraum mit unsauberen Tischen."

Reviewed on 29 Sep 2019

Hampton Inn Boston - Logan Airport
Boston Park Plaza

Boston Park Plaza

4 out of 5
50 Park Plaza at Arlington Street, Boston, MA
The price is £160 per night from 25 Jan to 26 Jan
Located in Back Bay, this historic hotel is within a 10-minute walk of Newbury Street, Boston Public Garden and Boston Common. Copley Place and Hynes Convention ...
4.3/5 Excellent! (6 reviews)
"I love the style and ambience. Staff are uniformly friendly. Nothing to dislike, other than that lobby area can get very crowded with conference attendees"

Reviewed on 4 Dec 2019

Boston Park Plaza

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Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
207 Porter St, Boston, MA
The price is £90 per night from 5 Feb to 6 Feb
Located in East Boston, this hotel is within 3 miles (5 km) of New England Aquarium, Faneuil Hall Marketplace and Long Wharf. Boston Harbor and TD Garden are ...
3/5 (1 review)
"Das mir zugewiesene Zimmer war sehr laut, es gab eine Klimaanlage direkt hinter meinem Bett, sodass nicht nur mein Bett samt Zimmerwand dauerhaft vibrierte, sondern auch ständig ein sehr unangenehmer Geräuchpegel herrschte! Leider war diese dauerhaft lärmende / vibrierende Klimaanlage aber in dem ..."

Reviewed on 7 Dec 2021

Embassy Suites Boston Logan Airport
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street, Boston, MA
The price is £123 per night from 30 Jan to 31 Jan
Located in Downtown Boston, this boutique hotel is steps away from Boston Opera House, The Freedom Trail and Orpheum Theater. Boston Common and Emerson College ...
5/5 Exceptional! (3 reviews)
"The location was great and the whole property was very modern and nicely decorated. All the staff were very friendly and helpful. Would happily stay here again!"

Reviewed on 4 Jan 2020

The Godfrey Hotel Boston
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
The price is £141 per night from 25 Jan to 26 Jan
Located in Seaport District, this romantic hotel is within a 5-minute walk of Liberty Wharf and Institute of Contemporary Art. Rockland Trust Bank Pavilion and ...
5/5 Exceptional! (4 reviews)
"Personnel très accueillant, quartier agréable. Chambre joliment decorée et en bon état"

Reviewed on 23 Aug 2021

Seaport Hotel Boston
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

*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.