$94 Cheap Flights from Boston (BOS) to Chicago (ORD)

View $94 flight on Tue, Jun 2, 2026Opens in a new window

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

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Cheap Flights from Boston to Chicago (BOS-ORD)

Prices were available within the past 7 days and start at $94 for one-way flights and $182 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Jun 9 - Tue, Jun 9
BOS
Boston
ORD
Chicago
$182 Roundtrip, found 5 hours ago
$182
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Tue, Jun 9 from Boston to Chicago, returning Tue, Jun 9, priced at $182 found 5 hours ago
Delta
Wed, Jun 3 - Tue, Jun 9
BOS
Boston
ORD
Chicago
$187 Roundtrip, just found
$187
Roundtrip
just found
Select Delta flight, departing Wed, Jun 3 from Boston to Chicago, returning Tue, Jun 9, priced at $187 just found
United
Tue, Jun 9 - Tue, Jun 9
BOS
Boston
ORD
Chicago
$187 Roundtrip, found 5 hours ago
$187
Roundtrip
found 5 hours ago
Select United flight, departing Tue, Jun 9 from Boston to Chicago, returning Tue, Jun 9, priced at $187 found 5 hours ago
American Airlines
Wed, Jun 3 - Tue, Jun 9
BOS
Boston
ORD
Chicago
$187 Roundtrip, just found
$187
Roundtrip
just found
Select American Airlines flight, departing Wed, Jun 3 from Boston to Chicago, returning Tue, Jun 9, priced at $187 just found
JetBlue Airways
Wed, Jun 3 - Wed, Jun 3
BOS
Boston
ORD
Chicago
$191 Roundtrip, found 5 hours ago
$191
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Wed, Jun 3 from Boston to Chicago, returning Wed, Jun 3, priced at $191 found 5 hours ago
American Airlines
Fri, Jun 5 - Tue, Jun 9
BOS
Boston
ORD
Chicago
$192 Roundtrip, just found
$192
Roundtrip
just found
Select American Airlines flight, departing Fri, Jun 5 from Boston to Chicago, returning Tue, Jun 9, priced at $192 just found
American Airlines
Sat, Jun 6 - Tue, Jun 9
BOS
Boston
ORD
Chicago
$196 Roundtrip, just found
$196
Roundtrip
just found
Select American Airlines flight, departing Sat, Jun 6 from Boston to Chicago, returning Tue, Jun 9, priced at $196 just found
United
Tue, Jun 9 - Tue, Jun 9
BOS
Boston
ORD
Chicago
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select United flight, departing Tue, Jun 9 from Boston to Chicago, returning Tue, Jun 9, priced at $197 found 5 hours ago
American Airlines
Thu, Jun 4 - Sat, Jun 6
BOS
Boston
ORD
Chicago
$199 Roundtrip, found 6 hours ago
$199
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Jun 4 from Boston to Chicago, returning Sat, Jun 6, priced at $199 found 6 hours ago
Frontier Airlines
Tue, Jul 14 - Wed, Jul 22
BOS
Boston
ORD
Chicago
$199 Roundtrip, found 6 hours ago
$199
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Jul 14 from Boston to Chicago, returning Wed, Jul 22, priced at $199 found 6 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. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $187
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $187

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 $94 and cheap return flights from $182 Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights generally range between $67 and $662, and roundtrip flights usually range from $195 to $1451. 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 Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
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 (BOS) to Chicago (ORD), with average return fares around $185. This is about 19% lower than the average price throughout the year, as travel demand decreases after the summer peak. Other cheap months to fly from Boston to Chicago include January and February.*Averages based on flights available on Expedia in the last year.
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 BOS to ORD:

  • American Airlines operates around 77 direct flights from BOS to ORD every week
  • United operates around 70 direct flights from BOS to ORD every week
  • Delta operates around 29 direct flights from BOS to ORD every week
  • JetBlue Airways operates around 12 direct flights from BOS to ORD every week
  • Japan Airlines operates around 14 direct flights from BOS to ORD every week

What is the cheapest airline that flies from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
JetBlue Airways is one of the cheapest airlines offering nonstop flights from Logan Intl. (BOS) to O'Hare Intl. (ORD), with round-trip tickets starting from around $260. 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.*Prices based on flights available on Expedia in the last year.
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) to Chicago, IL (ORD) 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. Delta offers the most daily flights from BOS to ORD, 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 (BOS) to Chicago (ORD) is typically in September or January. In September, you can expect prices to be around $185 for a return flight, making it a budget-friendly option. January also offers good fares at a similar price, but it's less popular, meaning you might enjoy a quieter travel experience.*Prices based on flights available on Expedia in the last year.
How many flights per day from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 27 nonstop flights per day from Logan Intl. (BOS) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Boston (BOS) to Chicago (ORD) typically departs at around 5:00 AM, operated by American Airlines. This seasonal service is active in April, allowing you to make the most of your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
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 (BOS-Logan Intl.) to Chicago (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 26% of passengers prefer this time window. Many major carriers, including American Airlines and United, offer flights during this window. This timing works well because it allows you to arrive in Chicago with plenty of time to start your day.
How long does it take to fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from BOS to ORD typically takes around 3 hours, covering approximately 864 miles. Connecting flights on this route usually add 3 hours to your travel time. 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.)?
Business class seats are offered on the BOS to ORD route with American Airlines.First class cabins are available on:

  • American Airlines
  • Delta Air Lines
  • United Airlines
  • Spirit Airlines

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) to Chicago, IL (ORD) typically costs between $739 - $1,134. A non-stop, one-way business class flight is usually around $353 - $588. 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.*Prices based on flights available on Expedia in the last year.
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 O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Ronald Reagan Washington National (DCA), John F. Kennedy Intl. (JFK) 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.) Chicago Vacation Packages 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
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Sun Country Airlines, United
Roundtrip price
$181
Distance
863 mi
Average flight time
1 hour 54 mins

Book with confidence

Boston to Chicago Flights

The cheapest times to fly from Boston to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Boston to Chicago are during the month of June. You can find some of the cheapest flights from Boston to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Boston to Chicago

Sunday is one of the best days to book for cheap flights from Boston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Boston to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Boston to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $94 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Boston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Boston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Boston to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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