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£95 Cheap Flights from Boston (BOS) to Chicago (ORD)

View £95 flight on Sat, 12 Sept 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at £95 for one-way flights and £189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Fri, 13 Nov - Tue, 17 Nov
BOS
Boston
ORD
Chicago
£189 Return, found 2 hours ago
£189
Return
found 2 hours ago
Select JetBlue Airways flight, departing Fri, 13 Nov from Boston to Chicago, returning Tue, 17 Nov, priced at £189 found 2 hours ago
JetBlue Airways
Wed, 21 Oct - Wed, 28 Oct
BOS
Boston
ORD
Chicago
£190 Return, found 2 days ago
£190
Return
found 2 days ago
Select JetBlue Airways flight, departing Wed, 21 Oct from Boston to Chicago, returning Wed, 28 Oct, priced at £190 found 2 days ago
JetBlue Airways
Fri, 11 Sept - Sat, 12 Sept
BOS
Boston
ORD
Chicago
£192 Return, found 3 days ago
£192
Return
found 3 days ago
Select JetBlue Airways flight, departing Fri, 11 Sept from Boston to Chicago, returning Sat, 12 Sept, priced at £192 found 3 days ago
JetBlue Airways
Wed, 21 Oct - Wed, 28 Oct
BOS
Boston
ORD
Chicago
£192 Return, found 2 days ago
£192
Return
found 2 days ago
Select JetBlue Airways flight, departing Wed, 21 Oct from Boston to Chicago, returning Wed, 28 Oct, priced at £192 found 2 days ago
JetBlue Airways
Fri, 11 Sept - Sat, 12 Sept
BOS
Boston
ORD
Chicago
£194 Return, found 3 days ago
£194
Return
found 3 days ago
Select JetBlue Airways flight, departing Fri, 11 Sept from Boston to Chicago, returning Sat, 12 Sept, priced at £194 found 3 days ago
JetBlue Airways
Thu, 10 Sept - Mon, 14 Sept
BOS
Boston
ORD
Chicago
£196 Return, found 3 days ago
£196
Return
found 3 days ago
Select JetBlue Airways flight, departing Thu, 10 Sept from Boston to Chicago, returning Mon, 14 Sept, priced at £196 found 3 days ago
American Airlines
Mon, 19 Oct - Tue, 20 Oct
BOS
Boston
ORD
Chicago
£196 Return, found 3 days ago
£196
Return
found 3 days ago
Select American Airlines flight, departing Mon, 19 Oct from Boston to Chicago, returning Tue, 20 Oct, priced at £196 found 3 days ago
Delta
Sat, 29 Aug - Thu, 3 Sept
BOS
Boston
ORD
Chicago
£219 Return, found 15 hours ago
£219
Return
found 15 hours ago
Select Delta flight, departing Sat, 29 Aug from Boston to Chicago, returning Thu, 3 Sept, priced at £219 found 15 hours ago
United
Mon, 5 Oct - Wed, 7 Oct
BOS
Boston
ORD
Chicago
£247 Return, found 2 days ago
£247
Return
found 2 days ago
Select United flight, departing Mon, 5 Oct from Boston to Chicago, returning Wed, 7 Oct, priced at £247 found 2 days ago
Alaska Airlines
Sat, 24 Oct - Wed, 28 Oct
BOS
Boston
ORD
Chicago
£349 Return, found 11 hours ago
£349
Return
found 11 hours ago
Select Alaska Airlines flight, departing Sat, 24 Oct from Boston to Chicago, returning Wed, 28 Oct, priced at £349 found 11 hours ago

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from £263
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from £263

Find the cheapest month to fly from Boston (BOS) to Chicago (ORD)

September is typically the cheapest month to fly

From £104 - £147 per traveller.

Frequently asked questions

How much does a flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from £95 and cheap return flights from £189 BOS to ORD with Expedia. One-way flights typically cost between £96 and £381, and return flights often range between £205 and £753. 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 BOS to ORD ticket fares go up or down.
What is the cheapest month to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is typically the cheapest month to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.), with average return fares around £139. 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) include January and February.
Which airlines fly direct from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are 5 airlines offering direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.). Here are some of the top carriers:
  • United operates 80 direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • American Airlines operates 74 direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • Delta operates 27 direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • JetBlue Airways operates 13 direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
  • British Airways operates 7 direct flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
How do I find cheap flights from Boston, MA (BOS) to Chicago, IL (ORD)?
To find a cheap flight from Boston, MA (BOS) to Chicago, IL (ORD), 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 time to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest months to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) are typically September and January, with average return flights around £139. However, the most popular months for this route, offering plenty of flight options, are July and April. If you're looking for a balance between good prices and a wide selection of flights, you might consider travelling in April or September, as these months often provide a good compromise.
What is the earliest flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 5:00 AM. This service is operated by American Airlines. This is a seasonal service, active in October. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A non-stop flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically takes around 3 hours, covering a distance of about 1,390 kilometers. If you opt for a one-stop flight, your journey will usually be longer, taking about 5 hours. Flights with two or more stops generally take around 7 hours 48 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.
Can you fly business or first class from Boston, MA (BOS) to Chicago, IL (ORD)?
Select the "Business class" and "First class" filters when looking for Boston, MA (BOS) to Chicago, IL (ORD) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How much is a business class flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically costs between £669 - £1182. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.
How do I earn miles on a Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare 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 Chicago, IL (ORD) from Boston, MA (BOS)?
If you're planning to travel to Chicago from Logan Intl. (BOS), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Ronald Reagan Washington National (DCA), or Liberty Intl. (EWR) before reaching Chicago. 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare 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 Boston, MA (BOS) to Chicago, IL (ORD)?
If you booked your Boston, MA (BOS) to Chicago, IL (ORD) 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
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, JetBlue Airways, United
Roundtrip price
£188
Distance
1381 km
Average flight time
1 hour 54 mins

Book with confidence

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 flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. 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 £189 and range up to £349.  

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 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 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.  

Compare flights from Boston to Chicago easily and book with confidence

Explore a world of travel with Expedia

*Available to Expedia members.