£82 Cheap Flights from Chicago (ORD) to Boston (BOS)

You can find cheap one-way flights from £82 and cheap return flights £163 ORD to BOS with Expedia. One-way flights typically cost between £100 and £293. 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 ORD to BOS ticket fares go up or down.

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 around £141. September sees lower prices because it falls after the peak summer travel season, when demand drops and airlines compete for bookings. January and February are also good months to find deals on this route.

There are 4 airlines offering direct flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.). These include:
* United operates 89 direct flights from ORD to BOS every week.
* American Airlines operates 78 direct flights from ORD to BOS every week.
* Delta operates 28 direct flights from ORD to BOS every week.
* JetBlue Airways operates 13 direct flights from ORD to BOS every week.

JetBlue Airways is one of the cheapest airlines offering nonstop return flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.), with tickets starting from around £128 for flights that can be booked for departure within the next year. American Airlines offers one of the cheapest connecting return flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.), with tickets starting from around £158. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

To find a cheap flight from Chicago, IL (ORD) to Boston, MA (BOS), 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.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) typically departs around 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 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.

When flying from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.), you have a few options. A non-stop flight typically takes around 2 hours 30 minutes. If you opt for a flight with one stop, the journey will usually take longer, averaging about 4 hours 48 minutes. For flights with two or more stops, you can expect a total travel time of around 7 hours. The distance between these two cities is approximately 1,390 kilometers. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic.

Select the "Business class" and "First class" filters when looking for Chicago, IL (ORD) to Boston, MA (BOS) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.

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.

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), or Orlando Intl. (MCO) before reaching Boston. Compare routes and airports on Expedia to find the best flight options for your travel plans.

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.

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.

If you booked your Chicago, IL (ORD) to Boston, MA (BOS) 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.