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

View AU$118 flight on Tue, 11 Aug 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 for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, 28 May - Fri, 29 May
BOS
Boston
ORD
Chicago
AU$210 Return, found 5 days ago
AU$210
Return
found 5 days ago
Select American Airlines flight, departing Thu, 28 May from Boston to Chicago, returning Fri, 29 May, priced at AU$210 found 5 days ago
American Airlines
Thu, 28 May - Fri, 29 May
BOS
Boston
ORD
Chicago
AU$225 Return, found 5 days ago
AU$225
Return
found 5 days ago
Select American Airlines flight, departing Thu, 28 May from Boston to Chicago, returning Fri, 29 May, priced at AU$225 found 5 days ago
American Airlines
Sat, 23 May - Sat, 30 May
BOS
Boston
ORD
Chicago
AU$234 Return, found 2 days ago
AU$234
Return
found 2 days ago
Select American Airlines flight, departing Sat, 23 May from Boston to Chicago, returning Sat, 30 May, priced at AU$234 found 2 days ago
American Airlines
Thu, 28 May - Fri, 29 May
BOS
Boston
ORD
Chicago
AU$241 Return, found 5 days ago
AU$241
Return
found 5 days ago
Select American Airlines flight, departing Thu, 28 May from Boston to Chicago, returning Fri, 29 May, priced at AU$241 found 5 days ago
Delta
Thu, 28 May - Fri, 29 May
BOS
Boston
ORD
Chicago
AU$245 Return, found 5 days ago
AU$245
Return
found 5 days ago
Select Delta flight, departing Thu, 28 May from Boston to Chicago, returning Fri, 29 May, priced at AU$245 found 5 days ago
Delta
Thu, 28 May - Fri, 29 May
BOS
Boston
ORD
Chicago
AU$258 Return, found 5 days ago
AU$258
Return
found 5 days ago
Select Delta flight, departing Thu, 28 May from Boston to Chicago, returning Fri, 29 May, priced at AU$258 found 5 days ago
American Airlines
Wed, 24 June - Fri, 26 June
BOS
Boston
ORD
Chicago
AU$261 Return, found 5 hours ago
AU$261
Return
found 5 hours ago
Select American Airlines flight, departing Wed, 24 June from Boston to Chicago, returning Fri, 26 June, priced at AU$261 found 5 hours ago
Delta
Fri, 1 May - Mon, 11 May
BOS
Boston
ORD
Chicago
AU$262 Return, found 6 days ago
AU$262
Return
found 6 days ago
Select Delta flight, departing Fri, 1 May from Boston to Chicago, returning Mon, 11 May, priced at AU$262 found 6 days ago
United
Thu, 28 May - Fri, 29 May
BOS
Boston
ORD
Chicago
AU$266 Return, found 5 days ago
AU$266
Return
found 5 days ago
Select United flight, departing Thu, 28 May from Boston to Chicago, returning Fri, 29 May, priced at AU$266 found 5 days ago
Delta
Thu, 28 May - Fri, 29 May
BOS
Boston
ORD
Chicago
AU$271 Return, found 5 days ago
AU$271
Return
found 5 days ago
Select Delta flight, departing Thu, 28 May from Boston to Chicago, returning Fri, 29 May, priced at AU$271 found 5 days ago

Frequently asked questions

How much does a flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
One-way flights typically cost between $303 and $1,121 and return flights often range between $657 and $2,933. 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 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 465 AUD. This is about 19% 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 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.)?
Enter BOS to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
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.
What is the best airline to fly with from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveller to traveller. If you like to fly early, DL offers early morning flights. If price is the most important factor, B6 typically offers the lowest fares. DL 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.
What is the best time to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) is September. This month offers a great balance, as it's both one of the cheapest and most popular times to travel. You can expect average return flight prices around 465 AUD, and with its popularity, you'll find plenty of flight options to choose from. This information is based on booking data from the past year.
How many flights per day from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
When flying from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.), you'll find approximately 28 nonstop flights available per day. For even more choice, look at flights that include layovers, as there are around 148 connecting flights per day. Some common connection points include LaGuardia (LGA), Ronald Reagan Washington National (DCA), and Liberty Intl. (EWR).
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 at approximately 5:00 AM local time, 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.
What day of the week has the most flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) on a Friday, with around 98 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include AA, DL, and UA. Fridays and Thursdays offer notably more flight options compared to other days of the week, making them great choices if you're looking for flexibility.
What are the most popular departure times for flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
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. This accounts for around 26% of total traffic. Heaps of major carriers, including American Airlines and United Airlines, offer flights during this window. Many travelers prefer these early morning flights to get a head start on their day in Chicago.
How long does it take to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying nonstop from BOS to ORD takes around 3 hours, with the route covering approximately 864 miles. Flights with a layover typically take 3 hours 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for BOS to ORD 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 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 from Logan Intl. (BOS)?
When traveling from Logan Intl. (BOS) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Nashville Intl. (BNA), 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-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
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.

Travel information

Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
AU$210
Distance
1381 km
Average flight time
1 hour 56 mins

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Your quick guide to flights from Boston to Chicago

Pick up great flights from Boston to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Boston to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Boston to Chicago that take around hours.

Find cheap flights from Boston to Chicago

From the great flight deals with prices currently ranging from AU$210 to AU$271, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Boston to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in May.

Reasons to book your flight from Boston to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Boston to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Your quick guide to flights from Boston to Chicago

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