Cheap Flights from Boston Logan International to Chicago O'Hare International

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

Find the cheapest month or even day of the year to fly to Chicago O'Hare International

Book the best Chicago O'Hare International fare with no extra fees

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

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

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

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

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

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

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

Boston to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 989
Cheapest month to flyOctober
Average flight time3 hrs, 3 mins
Most popular airlineAmerican Airlines
Average flights per week514

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

The best price we found for a return flight from Boston Logan International to Chicago O'Hare International is R 1,981. 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.
3 hours and 3 minutes is the average flight time from Boston Logan International to Chicago O'Hare International.
American Airlines, Qatar Airways and Alaska Airlines fly direct from Boston Logan International to Chicago O'Hare International.
As of September 2025, there are 514 flights per week flying from Boston Logan International to Chicago O'Hare International.
The cheapest month to fly from Boston Logan International to Chicago O'Hare International is usually October.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Boston Logan International Airport to Chicago O'Hare International Airport on Thursday, 23 October 2025.
Yes – the average flight time is 3 hours and 3 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 Chicago O'Hare 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, KLM offers the cheapest flight tickets to Chicago O'Hare International.

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

  • Around 2 hours 55 minutes is how long you'll be travelling on a direct flight from Logan International Airport to O'Hare International Airport.

  • The timezone in Chicago is UTC-5, which is one hour behind Boston.

  • Flights from BOS to ORD start at 05:10 — the first with American Airlines. The last departure is at 22:06 with American Airlines. In total, you can choose from 194 weekly Logan International Airport to O'Hare International Airport flights.

  • Arrive at the airport on time so you don't miss your BOS to ORD flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid any last-minute rush.

  • Flying during a peak time like August? Public holidays and other popular seasons can result in longer queues at check-in and security. Play things extra safe and arrive up to four hours ahead of international flights and two hours before domestic departures.

  • Plenty of airlines offer direct flights from Logan International Airport to O'Hare International Airport. Travel nonstop to Chicago with these popular carriers and get to know this amazing part of United States:

  • American Airlines is the top choice for travellers on this route.

  • American Airlines is the most punctual carrier operating BOS to ORD flights. A reliable 86.18% of its services on this route arrive without delay.

  • Think about adding a stopover when booking your ticket from Logan International Airport to O'Hare International Airport. Just deselect 'Direct flights only' to break up your trip, or perhaps see a new city along the way. Here's where you can stop between BOS and ORD:

    • Pittsburgh International Airport

    • Detroit Metropolitan Wayne County Airport

    • Baltimore/Wash International Thurgood Marshall Airport

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

  • The cheapest price we've found for a one-way Logan International Airport to O'Hare International Airport flight is R 989. A return fare right now is R 1,981. Depending on the availability when you book, these fares could change.

  • Book seven months before your departure date. After crunching the numbers on our calendar, this is how far you'll want to book ahead to secure cheap tickets from BOS to ORD.

  • The cheapest month for flights from Logan International Airport to O'Hare International Airport is June. Use the 'Whole month' tool to see the lowest prices if you have a flexible schedule.

  • You don't need to check back in every day to find out if fares have dropped when you create a Price Alert. We'll send you an update as soon as a special offer becomes available on cheap flights from BOS to ORD.

  • Discover the ideal flight for you by using the filters. To see the 'Fastest,' 'Best' or 'Cheapest' flights from Logan International Airport to O'Hare International Airport, use the 'Sort by' tool. You can also filter by arrival and departure times, airline, and journey duration.

Handy information about Logan International Airport (BOS)

  • You'll find BOS at One Harborside Drive.

  • Of all flights leaving Logan International Airport, 73.94% arrive as scheduled at their destination.

  • Central Boston to Logan International Airport is approximately 5 kilometres. Depending on traffic, it'll take about 10 minutes to get there if you're catching a cab, ride-sharing or driving.

  • The trip on public transport takes roughly 25 minutes.

  • Looking for a convenient hotel near BOS? If you've booked an early flight from Logan International Airport to O'Hare International Airport, these stays will put you moments from your departure lounge:

Arriving at O'Hare International Airport (ORD)

Getting from O'Hare International Airport (ORD) to central Chicago

  • You'll find ORD at 10000 West O'Hare.

  • O'Hare International Airport to central Chicago has a drive time of around 35 minutes. It's approximately 40 kilometres away.

  • It typically takes 55 minutes when travelling by public transport.

When to fly to O'Hare International Airport (ORD)

  • August is the busiest month for flights from Logan International Airport to O'Hare International Airport. To escape the crowds, travel to Chicago in January.

  • Before locking in your flight from Logan International Airport to O'Hare International Airport, think about the kind of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from BOS to ORD around that time if you want to travel in cooler conditions.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be explored once you've taken in the sights of Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Experience major highlights starting with The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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