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Check out our best offers departing from Boston among more than 400 airlines now!

Use the search-box to select your departure city or airport and get the best prices. Please, note these prices below are 'from'.

Cheap flights Boston - Chicago

Information about flights from Boston to Chicago

lastminute.com would like to be the perfect travel tool for all your travelling needs. The lastminute.com App is also available for the smartphone so you don’t miss out and being able to use our search engine from wherever you are.

Hi and welcome to your perfect solution to finding low cost flights in just a few clicks! When searching for a low cost flight from Boston to Chicago, all you have to do is complete the search form and in no time you will be flying off to Chicago.

As well as your flight from Boston to Chicago, guess what, it’s also really easy with lastminute.com to have a car waiting for you when you arrive as well as accommodation in Chicago.

When you’re looking to get away and not interested in a precise date, take a look at our flight offers this month. Flight deals from Boston to Chicago are great time of year. Be inspired!

lastminute.com’s facebook page gives you an easy way to stay up to date with giveaways and promotions on low cost flights and holidays to Chicago from Boston.



Maybe you are interested in  Cheap flights to Boston  or search  Cheap flights from Chicago to Boston  Now's your chance!


Cheap flights from United Kingdom cities to Chicago

Cheap flights from outside of United Kingdom to Chicago

Frequently asked questions

How do I buy tickets from different airlines at once and save money?

Our system combines airlines automatically to find the cheapest flights available. That way you can save money and don't have to buy your tickets separately.

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 should I do 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.**

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Cost of living in Boston compared with Chicago

Food and drinks Boston Chicago Difference
Beer (0.5 litre) £2.00 £2.00 0%
Coffee £3.00 £3.00 0%
Meal at McDonald's £7.00 £6.00 -14%
Water (0.33 litre) £1.00 £1.00 0%
Transportation Boston Chicago Difference
Monthly pass £70.00 £86.00 +23%
One way tube ticket £2.00 £2.00 0%
Taxi starting price (normal tariff) £2.00 £3.00 +50%
Clothing Boston Chicago Difference
1 summer dress in a chain store (Zara, H&M,...) £25.00 £32.00 +28%
1 pair of jeans (Levi's 501 or similar) £38.00 £43.00 +13%
Salaries Boston Chicago Difference
Average monthly disposable salary (net) £3,689.00 £3,321.00 -10%