Cheap Flights from Chicago to Boston

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Frequently asked questions

How long is the flight from ORD to BOS?
The trip from Chicago to Boston will only take around 2 hours and 25 minutes, so there's no need to worry about dreaded jet lag. Yep, you can leave your NASA-designed neck pillows and brick-sized novels at home.
Are there non-stop flights between ORD and Logan Intl. Airport (BOS)?
Your time is valuable. We get ya. You'll find multiple airlines that fly straight from O'Hare Airport to Logan Intl. Airport (BOS) — like United Airlines and American Airlines — so you don't need to lose time waiting for a connecting flight.
What airlines fly non-stop from O'Hare Airport to BOS?
Here's some good news. You won't have to waste time ambling around some random airport when jetting between O'Hare Intl. Airport (ORD) and BOS. You'll find a good number of airlines that have direct flights every month. Take a look at these top options:

  • United Airlines - (UA) with 208 flights every month
  • American Airlines - (AA) with 199 flights every month
  • Delta - (DL) with 147 flights every month
  • JetBlue - (B6) with 56 flights every month

How many flights are flown between O'Hare Intl. Airport (ORD) and Logan Intl. Airport?
Scoring a seat on a flight from Chicago to Boston is ridiculously easy, with 20 daily services to pick from. So get cracking with your packing!
What are the cheapest days to book a flight?
Looking at lastminute.com.au travel demand in 2021, Wednesdays and Sundays are often the best days to book flights, when prices are generally at their cheapest. You may be tempted to wait to finalise your booking on Saturdays, but our data tells us ticket prices are actually highest on Saturdays. Something to consider when planning your next holiday!
What is the cheapest month to fly?
Here's the lowdown on the lowest airfares: May is the cheapest month to fly. When looking at 2021 flight demand on lastminute.com.au, flights departing in May generally have the lowest ticket prices. As for the most expensive month to fly, our demand data found that on average, airfares are highest in December.
How far in advance can you book a flight?
Itching to book your dream trip? We totally get it. You can start looking at flights on lastminute.com.au as early as 12 months in advance, but just keep in mind some airlines may not release all their available fares that early. But good news for last minute travellers, with 2021 lastminute.com.au data proving spontaneous travellers can still bag a bargain with some of the cheapest airfares appearing just 1 week prior to travel.*According to flight demand on lastminute.com.au from January to December 2021. Savings are subject to change and may vary depending on selections made.
O'Hare Intl. to Logan Intl. Flight
Origin airport
O'Hare Intl.
Origin city name
Chicago
Destination airport
Logan Intl.
Destination city name
Boston
Distance
1381 km

Last Minute Chicago to Boston Flights

If you’re searching for cheap Chicago to Boston flights, we’ve got you covered. Whether you’re travelling for business or booking a holiday getaway, Lastminute.com.au sources discount airfares to get you from Chicago to Boston, for less.

Booking a flight should be easy and we’re here to help. Use our simple search tool to find early bird fares or cheap last minute flights, including great economy deals or business class tickets. We make it easy to compare arrival and departure times, find check in information, as well as provide flight status details and round the clock customer support. Even if you’ve left getting from Chicago to Boston to the last second, finding a flight is easy with Lastminute.com.au!

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*Prices are "from" prices based on the lowest available fare on the sample travel dates for one adult and will be confirmed prior to any payment being made. The price is not guaranteed until paid in full by cleared funds and your tickets are issued. Fees may apply for checked baggage. There may be an additional fee based on your payment type and flight selected. Total purchase price, inclusive of any applicable fees, is displayed on the flight details page prior to booking confirmation. Blackout dates and other restrictions may apply. Fares may be non-refundable (subject to applicable laws) and are not transferable. Name changes may not be permitted.Offers are subject to availability and may be discontinued without notice. Conditions apply.