CA $151 Cheap Flights from Boston (BOS) to Chicago (ORD)

You can find cheap one-way flights from CA $151 and cheap return flights CA $301 BOS to ORD with Expedia. One-way flights typically cost between CA$180 and CA$716 and return flights often range between CA$385 and CA$1,416. 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.

The cheapest months to fly from Boston, MA (BOS) to Chicago, IL (ORD) 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 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.

JetBlue Airways is one of the cheapest airlines offering nonstop return flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.), with tickets starting from around CA$210 for flights that can be booked for departure within the next year. JetBlue Airways also offers one of the cheapest connecting return flights on this route, with tickets starting from around CA$401. These prices are per adult, for economy/coach class. 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare 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.

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

You'll find approximately 28 nonstop flights per day from Boston Logan International (BOS) to Chicago O'Hare International (ORD). For even more choices, look at flights that include layovers, as there are around 144 connecting flights per day. Some common connection points include LaGuardia (LGA), Ronald Reagan Washington National (DCA), and Liberty Intl. (EWR).

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.

You'll generally find the most flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) on a Friday, with around 104 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include American Airlines, Delta, and United. 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.

The most popular departure times for flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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 early flights as they allow you to arrive at your destination with plenty of time to start your day.

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.

You can fly business class or first class between BOS and ORD.

You can fly business class with Frontier Airlines and Delta.

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

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

Typically, booking a last minute flight from Boston, MA (BOS) to Chicago, IL (ORD) 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 Boston, MA (BOS) to Chicago, IL (ORD) 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare 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.