Can I combine different airlines on the same trip?

Of course. We offer you the possibility of booking with more than 400 airlines so that you can find the cheapest fare or the most convenient combination: outbound flight with one airline and return flight with another.

Is lastminute.com a trustworthy travel brand?

In 1998, lastminute.com was one of the first online travel agencies. Currently, we are selling over 380,000 flights per year – and working hard on bringing travellers wherever they want to go.

What options are there if I have to change my flight?

lastminute.com offers flexibility services for purchase at the time of your booking. These services entitle you to change or cancel your flights without handling fee.**Flexibility services are available on selected flights only. Please read our T&Cs for more information.

I am afraid to lose my luggage, every time I fly. What can I do?

lastminute.com offers a range of baggage protection services, so that you are covered in case your luggage is delayed or lost.****Baggage protection services are available on selected flights only. Please read our T&Cs for more information.

How long does a flight take between Chicago and Boston?

The flight from Chicago to Boston has a duration of 2h 28m.

What are the cheapest flights from Chicago to Boston?

The cheapest one-way flight costs £87 flying with JetBlue Airways and the cheapest return flight costs £151 with JetBlue Airways.

How many airports are there in the city of Chicago?

Chicago has 3 airport: CHI - All airports, Chicago O'Hare International Airport, Midway International Airport.

How many airports does Boston have?

There are 1 airports in Boston: Logan Airport

Which Boston airport is the most central?

The most central airport is Logan Airport, 3.5km.

Which airlines have flights from Chicago to Boston?

There are 4 airlines with flights from Chicago to Boston; Those that offer lower prices are JetBlue Airways (£134).

Schedules of the first and last flight from Chicago to Boston

The first flight from Chicago to Boston is at 14:22 and the last flight departs at 23:51.

Cheap flights from Chicago to Boston

Fly smart, spend less

Flights to Boston from Chicago

Cheap flights from Chicago to Boston from £87. Chicago (United States) - Boston (United States) return flights from £151. From 25/07/2026 (Saturday) - 01/08/2026 (Saturday). Check for the dates with the lowest prices and find the cheapest rates.

Direct flights from Chicago to Boston

Book direct flights from Chicago to Boston for a smooth journey.

25 Jul - 01 Aug • 7 nights

11 Aug - 13 Aug • 2 nights

25 Jul - 01 Aug • 7 nights

11 Aug - 13 Aug • 2 nights

25 Jul - 27 Jul • 2 nights

23 Jul - 26 Jul • 3 nights

Flights from Chicago to Boston one way

Find one-way flights from Chicago to Boston at great prices.

12 Aug

12 Aug

18 Aug

19 Aug

25 Aug

02 Sept

Cheapest flights from Chicago to Boston

Get the cheapest flights from Chicago to Boston today.

25 Jul - 01 Aug • 7 nights

11 Aug - 13 Aug • 2 nights

25 Jul - 27 Jul • 2 nights

11 Aug - 13 Aug • 2 nights

25 Jul - 01 Aug • 7 nights

25 Jul - 27 Jul • 2 nights

Cheap flights from Chicago O'Hare International Airport to Boston

Find cheap flights from Chicago O'Hare International Airport to Boston now.

11 Aug - 13 Aug • 2 nights

04 Aug - 06 Aug • 2 nights

23 Jul - 26 Jul • 3 nights

26 Jun - 03 Jul • 7 nights

25 Jul - 27 Jul • 2 nights

25 Jul - 01 Aug • 7 nights

Cheap flights from Midway International Airport to Boston

Find cheap flights from Midway International Airport to Boston now.

11 Aug - 13 Aug • 2 nights

25 Jul - 01 Aug • 7 nights

25 Jul - 27 Jul • 2 nights

23 Jul - 26 Jul • 3 nights

Chicago to Boston flight information

DEPARTING FROM:

Midway International Airport, more

ARRIVING IN:

Logan Airport

AIRLINES:

American Airlines, JetBlue Airways, more

AVG FLIGHT TIME:

2h 28m

More information about flights to Boston from Chicago

Information about flights from Chicago to Boston

Once you have your flight Chicago-Boston booked you can always use lastminute.com to organise the rest of your trip just the way you want it. lastminute.com allows you to book a hotel, car hire, tours and activities in Boston.

Not only can you use the lastminute.com website to search low cost flights, but we have even preselected some flight offers from Chicago to Boston for you to save you time.

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FAQs Chicago to Boston flights

FAQs

Of course. We offer you the possibility of booking with more than 400 airlines so that you can find the cheapest fare or the most convenient combination: outbound flight with one airline and return flight with another.

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