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

You can find cheap one-way flights from AU$102 and cheap return flights AU$285 ORD to BOS with Expedia. One-way flights typically cost between AU$190 and AU$557. 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.

The cheapest months to fly from Chicago, IL (ORD) to Boston, MA (BOS) are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares 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.

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 airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) will differ from traveler to traveler. If you like to fly early, Delta offers early morning flights. If price is the most important factor, JetBlue Airways typically offers the lowest fares. American Airlines offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.), which is great 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.

The cheapest months to fly from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) are typically September and January, with average return flights around AU$282. However, the most popular months for this route, meaning you'll find plenty of flight options, are August and November. If you're looking for a balance between good value and a wide selection of flights, you might consider booking in September, as it offers lower prices while still being close to a popular travel period.

You'll find approximately 30 nonstop flights per day from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS). For even more choices, look at flights that include layovers, as there are around 158 connecting flights daily. Some common connection points include LaGuardia (LGA), Hartsfield-Jackson Atlanta International Airport (ATL), and Liberty International Airport (EWR).

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.

You'll find the most flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.) on a Friday, with around 99 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include American Airlines, United, and Delta. Fridays see notably more flight options compared to other days of the week, making it a popular choice for travellers.

The most popular departure times for flights from Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) are in the early morning, from 6am to 9am. Many major carriers, including American Airlines, United and Delta, offer flights during this window. Many travellers prefer these times because it allows them to arrive in Boston early, giving them a full day for business or leisure activities.

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.

Yes, you can fly business class or first class between ORD and BOS. You can fly business class with Frontier Airlines and Delta.

First class cabins are available on Spirit Airlines, Alaska Airlines, Delta, United, and American Airlines.

It's easy to earn miles on a Chicago, IL (ORD) to Boston, MA (BOS) 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) to Boston, MA (BOS) 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) to Boston, MA (BOS) 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.