£62 Cheap Flights from Chicago (ORD) to Boston (BOS)

View £62 flight on Wed, 26 Aug 2026Opens in a new window

Popular airlines from Chicago O'Hare International Airport (ORD) to Logan International Airport (BOS)

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

Prices were available within the past 7 days and start at £62 for one-way flights and £124 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Wed, 20 May - Wed, 27 May
ORD
Chicago
BOS
Boston
£124 Return, found 6 days ago
£124
Return
found 6 days ago
Select JetBlue Airways flight, departing Wed, 20 May from Chicago to Boston, returning Wed, 27 May, priced at £124 found 6 days ago
Delta
Tue, 28 Jul - Tue, 4 Aug
ORD
Chicago
BOS
Boston
£124 Return, found 7 hours ago
£124
Return
found 7 hours ago
Select Delta flight, departing Tue, 28 Jul from Chicago to Boston, returning Tue, 4 Aug, priced at £124 found 7 hours ago
JetBlue Airways
Wed, 29 Jul - Mon, 3 Aug
ORD
Chicago
BOS
Boston
£127 Return, found 7 hours ago
£127
Return
found 7 hours ago
Select JetBlue Airways flight, departing Wed, 29 Jul from Chicago to Boston, returning Mon, 3 Aug, priced at £127 found 7 hours ago
JetBlue Airways
Thu, 16 Jul - Mon, 20 Jul
ORD
Chicago
BOS
Boston
£131 Return, found 2 days ago
£131
Return
found 2 days ago
Select JetBlue Airways flight, departing Thu, 16 Jul from Chicago to Boston, returning Mon, 20 Jul, priced at £131 found 2 days ago
JetBlue Airways
Thu, 30 Jul - Mon, 3 Aug
ORD
Chicago
BOS
Boston
£132 Return, found 7 hours ago
£132
Return
found 7 hours ago
Select JetBlue Airways flight, departing Thu, 30 Jul from Chicago to Boston, returning Mon, 3 Aug, priced at £132 found 7 hours ago
JetBlue Airways
Fri, 29 May - Sat, 6 Jun
ORD
Chicago
BOS
Boston
£135 Return, found 10 hours ago
£135
Return
found 10 hours ago
Select JetBlue Airways flight, departing Fri, 29 May from Chicago to Boston, returning Sat, 6 Jun, priced at £135 found 10 hours ago
Delta
Fri, 31 Jul - Tue, 4 Aug
ORD
Chicago
BOS
Boston
£138 Return, found 7 hours ago
£138
Return
found 7 hours ago
Select Delta flight, departing Fri, 31 Jul from Chicago to Boston, returning Tue, 4 Aug, priced at £138 found 7 hours ago
American Airlines
Fri, 12 Jun - Mon, 15 Jun
ORD
Chicago
BOS
Boston
£141 Return, found 1 day ago
£141
Return
found 1 day ago
Select American Airlines flight, departing Fri, 12 Jun from Chicago to Boston, returning Mon, 15 Jun, priced at £141 found 1 day ago
United
Sun, 2 Aug - Wed, 5 Aug
ORD
Chicago
BOS
Boston
£217 Return, found 7 hours ago
£217
Return
found 7 hours ago
Select United flight, departing Sun, 2 Aug from Chicago to Boston, returning Wed, 5 Aug, priced at £217 found 7 hours ago
Alaska Airlines
Wed, 27 May - Fri, 29 May
ORD
Chicago
BOS
Boston
£401 Return, found 2 days ago
£401
Return
found 2 days ago
Select Alaska Airlines flight, departing Wed, 27 May from Chicago to Boston, returning Fri, 29 May, priced at £401 found 2 days ago

Alternative airports near Boston

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BOS. Cheapest and Closest option available. Average driving time to city centre is 7 minutes. Flights from £179
BOS
Logan Intl.
CheapestClosest
Average driving time to city centre7 min
Flights from £179

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) cost?
One-way flights typically cost between £75 and £322 and return flights often range between £237 and £605. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Anaa (AAA) to Toronto, ON (YYZ-Pearson Intl.) ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
September is typically the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.), with average return fares of approximately £141. This is about 17% lower than the average price throughout the year. September often sees lower prices as the summer travel rush ends and before the holiday season begins, leading to reduced demand. Other cheap months to fly from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) include January and February.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
Enter ORD to BOS and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
The best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) will differ from traveller to traveller. If you like to fly early, UA offers early morning flights. If price is the most important factor, B6 typically offers the lowest fares. UA offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.), which is brilliant if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
When you're planning your trip from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS), September is often a great choice. While January is also one of the cheapest months, September offers a good balance of lower prices, with average return flights around £141, and still has plenty of flight options available. This means you can often find a good deal without sacrificing convenience, making it a smart time to travel.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
There are approximately 28 nonstop flights per day from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.). For even more choice, look at flights that include layovers, as there are around 174 connecting flights per day. Some common connection points include LaGuardia (LGA), Liberty Intl. (EWR), and Hartsfield-Jackson Atlanta Intl. (ATL).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) typically departs at approximately 12:00 AM local time, operated by American Airlines. This is a seasonal service active in December. An early departure like this can help you maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
You'll typically find the most flights from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) on a Friday, with around 96 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include American Airlines, United Airlines, and Delta Air Lines. Fridays offer notably more flight options compared to other days of the week, making it a great day to travel if you're looking for flexibility.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
The most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) are in the morning, from 6am to 9am. About 30% of passengers prefer this time. This timing works well because it allows you to get an early start to your day in Boston.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
Flying nonstop from ORD to BOS takes around 2 hours 30 minutes, with the route covering approximately 864 miles. Flights with a layover typically take 2 hours 50 minutes longer than direct options. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
Select the "Business class" and "First class" filters when looking for ORD to BOS flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Boston from O'Hare Intl. (ORD)?
If you're planning to travel to Boston from O'Hare Intl. (ORD), you can fly directly into Logan Intl. (BOS) Some flights may connect through major hubs like Nashville Intl. (BNA), Hopkins Intl. (CLE), Orlando Intl. (MCO) before reaching Boston. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, JetBlue Airways, United
Return price
£120
Distance
1381 km
Average flight time
3 hours 24 mins

Book with confidence

Compare flights from Chicago to Boston easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to Boston. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Logan Intl. in just hours. 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 £124 and range up to £401.  

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 May, 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.  

Compare flights from Chicago to Boston easily and book with confidence

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*Available to Expedia members.