
Popular airlines from Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD)
- JetBlue Airways
JetBlue Airways
- Alaska Airlines
Alaska Airlines
- American Airlines
American Airlines
- United
United
- Delta
Delta
- Plan, book, fly with confidence
trending down icon Be in the knowGet alerts if flight prices drop or rise*bex rewards loyalty icon Book smarterSave up to 25% on select hotels after you book a flight*payments icon
Cheap Flights from Boston (BOS) to Chicago (ORD)
Prices were available within the past 7 days and start at £44 for one-way flights and £94 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.










Find the cheapest month to fly from Boston (BOS) to Chicago (ORD)
September is typically the cheapest month to fly
Graph displaying average flight prices per month
Origin airport | Logan Intl. |
Destination airport | O'Hare Intl. |
Airlines serving | Alaska Airlines, American Airlines, Delta, JetBlue Airways, United |
Return price | £93 |
Distance | 1381 km |
Average flight time | 1 hour 52 mins |
Compare flights from Boston to Chicago easily and book with confidence
For travelling on business or for pleasure, Expedia makes it easy to book your flights from Boston to Chicago. Operating between them 68 flights per day, 20 airlines cover the route. And American Airlines, Qatar Airways, KLM, JAL, Icelandair, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, JetBlue, Avianca, Cathay Pacific, Royal Jordanian, SAS, Hawaiian Airlines, Iberia, ANA, Korean Air, TAP Air Portugal, WestJet, Virgin Atlantic, British Airways fly direct, getting you to O'Hare Intl. in just 0hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Logan Intl. to O'Hare 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 Logan Intl. (BOS) to O'Hare Intl. (ORD)
The easiest way to view the best deals on flights from Boston to Chicago 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 Logan Intl. to O'Hare Intl. start at just £94 and range up to £291.
To find an even better deal, try
- being flexible on your dates – midweek flights can be cheaper
- looking for other airports near Boston and Chicago
- booking your flight during September, the cheapest month on this route
- varying your flight times – early morning and late at night are sometimes cheaper
Why you should book your Boston to Chicago flight with Expedia!
We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Logan Intl. to O'Hare 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.
Frequently asked questions
Explore a world of travel with Expedia
- Trending Routes
- Trending Flights
- Top Flights Destinations
- Related Airlines
- Nearby Airports
- Cheap Flights from Other Airports
- Expedia's Latest Trends
Top Routes from Boston
- Boston to London (BOS - LCY)
- Boston to Edinburgh (BOS - EDI)
- Boston to Barcelona (BOS - BCN)
- Boston to Reykjavik (BOS - KEF)
- Boston to Florence (BOS - FLR)
- Boston to New York (BOS - JFK)
- Boston to Seville (BOS - SVQ)
- Boston to Porto (BOS - OPO)
- Boston to Athens (BOS - ATH)
- Boston to London (BOS - LHR)
- Boston to Lisbon (BOS - LIS)
- Boston to Bari (BOS - BRI)
Top Routes from Boston
Top Flight Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Chicago
- Flights to Myrtle Beach
- Flights to San Diego
- Flights to Panama City Beach
- Flights to Destin
- Flights to Los Angeles
- Flights to Ocean City
- Flights to Miami
- Flights to Boston
- Flights to Nashville
- Flights to Atlantic City
- Flights to Pigeon Forge
- Flights to Atlanta
- Flights to San Francisco
- Flights to Virginia Beach
- Flights to Gulf Shores
- Flights to Seattle
Chicago
Manchester
Providence
Nearby Airports
- Norwood Memorial Airport (OWD)
- Laurence G. Hanscom Field Airport (BED)
- Lawrence Municipal Airport (LWM)
- Plymouth Municipal Airport (PYM)
- Worcester Regional Airport (ORH)
- Manchester-Boston Regional Airport (MHT)
- Provincetown Municipal Airport (PVC)
- New Bedford Regional Airport (EWB)
- T.F. Green Airport (PVD)
- Portsmouth Intl. Airport (PSM)
Expedia's Latest Trends
- Flights from London to Cincinnati
- Flights from London to Seattle
- Flights from Las Vegas to London
- Flights from London to Anchorage
- Flights from London to Philadelphia
- Flights from London to Columbus
- Flights from Las Vegas to New York
- Flights from Las Vegas to Los Angeles
- Flights from London to Fort Lauderdale
- Flights from London to New York
- Flights from Las Vegas to San Francisco
- Flights from London to Cleveland
- Flights from London to Pittsburgh
- Flights from Toronto to New York
- Flights from Manchester to Las Vegas
- Flights from Los Angeles to Las Vegas
- Flights from Chicago to London
- Flights from London to Chicago
- Flights from Dallas to London
- Flights from Orlando to New York
- Flights from Manchester to Dallas
- Flights from San Francisco to Las Vegas
- Flights from New York to Las Vegas
- Flights from London to New York
- Flights from London to San Diego
- Flights from Dublin to Las Vegas
- Flights from Glasgow to Las Vegas
- Flights from London to Las Vegas
- Flights from Manchester to Chicago
- Flights from London to Dallas