Cheap Flights from Chicago to Boston

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Compare Chicago O'Hare International to Boston Logan International flight deals

Find the cheapest month or even day of the year to fly to Boston Logan International

Book the best Boston Logan International fare with no extra fees

Flight deals from Chicago O'Hare International to Boston Logan International

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International to Boston Logan International? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago O'Hare International to Boston Logan International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to Boston Logan International flights are currently cheapest in April.

Direct flights from Chicago O'Hare International to Boston Logan International

Chicago O'Hare International to Boston Logan International: Alternative routes

Compare routes from Chicago O'Hare International to Boston below. You may find an airport to fly into that's cheaper, faster, or easier than Boston Logan International.

Chicago to Boston: Flight information

The things to know before you go.
Cheapest flight found$154
Cheapest month to flyApril
Average flight time2 hrs, 29 mins
Most popular airlineAmerican Airlines
Average flights per week651

Finding cheap flights from Chicago O'Hare International to Boston Logan International: Frequently asked questions

The best price we found for a return flight from Chicago O'Hare International to Boston Logan International is $154. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 29 minutes is the average flight time from Chicago O'Hare International to Boston Logan International.
American Airlines, Alaska Airlines and Qatar Airways fly direct from Chicago O'Hare International to Boston Logan International.
As of April 2025, there are 651 flights per week flying from Chicago O'Hare International to Boston Logan International.
The cheapest month to fly from Chicago O'Hare International to Boston Logan International is usually April 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to Boston Logan International Airport on Friday, 11 April 2025.
Yes – the average flight time is 2 hours and 29 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Boston Logan International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Boston is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, United offers the cheapest flight tickets to Boston Logan International.

Travelling from O'Hare International Airport (ORD) to Logan International Airport (BOS): what you need to know

  • The average time for a direct flight from O'Hare International Airport to Logan International Airport is 2 hours 26 minutes. Boston's timezone is UTC-4, making Boston 1 hour ahead of Chicago.

  • Each week, there are 193 flights from O'Hare International Airport to Logan International Airport. If you want to jet off early, opt for the 05:10 American Airlines flight. If you're keen to make the most of your day before you fly, the last flight from ORD to BOS is 22:14 with Spirit Airlines.

  • Peak months like August or holiday periods such as spring break and Christmas will mean bigger waits at check-in and security. Be on the safe side and get to the airport even earlier. Arriving two hours before domestic flights and up four hours ahead of an international flight is a wise idea.

  • A range of airlines operate direct flights from O'Hare International Airport to Logan International Airport, so jetting off to Boston (and then seeing more of United States!) is easy. The most popular carriers that fly between ORD and BOS include:

  • If you prefer a stopover for your flight from O'Hare International Airport to Logan International Airport, just deselect 'Direct flights only' and explore your options. Here are the most popular stopovers between ORD and BOS:

    • Baltimore/Wash International Thurgood Marshall Airport

    • Philadelphia International Airport

    • Pittsburgh International Airport

How to find the cheapest flights from O'Hare International Airport (ORD) to Logan International Airport (BOS)

  • The best price we've seen for a one-way ticket from O'Hare International Airport to Logan International Airport is $77. The cheapest price for a return flight is $154. Bear in mind that fares may change due to availability when booking.

  • Score cheap flight tickets from ORD to BOS by booking 10 months ahead. Based on our research, that's the sweet spot for landing a bargain.

  • June is the cheapest month for tickets from O'Hare International Airport to Logan International Airport. If you prefer to fly during a different time of year, the 'Whole month' tool will show you the lowest airfares for each month.

  • Finding a cheap ticket from ORD to BOS is a breeze with Price Alerts. Simply create one of these automatic alerts and we'll notify you as soon as there's a better deal.

  • Tailor your flights with filters. Select your departure and arrival times, airlines and total journey duration. You can also sort the results by 'Fastest,' 'Cheapest' or 'Best' flights from O'Hare International Airport to Logan International Airport.

Handy information about O'Hare International Airport (ORD)

Arriving at Logan International Airport (BOS)

Getting from Logan International Airport (BOS) to central Boston

  • Logan International Airport to the centre of Boston takes around 12 minutes in a car. It's approximately 5 kilometres away. See what options are available, such as cabs, car rentals or ride-sharing.

  • If you're travelling by public transport, expect a journey of roughly 23 minutes.

When to fly to Logan International Airport (BOS)

  • It's time to work out your travel dates for your flight from O'Hare International Airport to Logan International Airport. August is the busiest month to visit Boston. If you like a quieter vibe, go in May.

  • Book your flight from O'Hare International Airport to Logan International Airport for July if you'd like to go to Boston during its warmest month. Expect temperatures of between 16ºC and 29ºC.

  • January has average temperatures of between -8ºC and 6ºC. Search for cheap flight tickets from ORD to BOS around that time if you like travelling in cooler conditions.

More about Boston

  • When it comes to looking for somewhere to rest your head, you'll find the best stays in Boston right here. Browse these options as soon as you've booked your flight from ORD to BOS:

  • Freedom Trail and Museum of Fine Arts Boston are a couple of leading attractions to add to your Boston must-do list. Keep the adventure rolling by checking out Boston Tea Party Ships & Museum.

Complete your Boston trip with hotels and a car rental

  • You've booked a cheap ticket to Logan International Airport — next up is finding a place to stay, and perhaps even a set of wheels. We've compared prices across hundreds of companies to bring you the best hotels and car rental deals in Boston.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.