Cheap Flights from Chicago (ORD) to Boston (BOS) from £43

Cheap Flights from Chicago (ORD) to Boston (BOS)

Prices were available within the past 7 days and starts at £43 for one-way flights and £85 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
United
American Airlines
United
United
American Airlines
United
United
United
United
American Airlines
Delta
Delta
JetBlue Airways
JetBlue Airways
American Airlines
United
United
American Airlines
JetBlue Airways
Flight from Chicago to Boston route information
Origin AirportO'Hare Intl.
Destination AirportLogan Intl.
Airlines ServingAmerican Airlines, Delta, JetBlue Airways, United
Flight Price£84
Distance1381 km

Frequently asked questions

Compare flights from Chicago to Boston easily and book in confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to Boston. Operating between them 64 flights per day, 20 airlines cover the route. And American Airlines, Qatar Airways, KLM, JAL, Icelandair, Azul, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, JetBlue Airways, SAS, Hawaiian Airlines, ANA, Virgin Atlantic, British Airways fly direct, getting you to Logan Intl. in just 2hours. If you have a preferred carrier, use our advanced search tool to find the right flight from O'Hare Intl. to Logan Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from O'Hare Intl. (ORD) to Logan Intl. (BOS) 

The easiest way to view the best deals on flights from Chicago to Boston today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from O'Hare Intl. to Logan Intl. start at just £85 and range up to £102.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Chicago and Boston
  • booking your flight during November, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Chicago to Boston flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from O'Hare Intl. to Logan Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Providence