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CA $150 Cheap Flights from Chicago (ORD) to Boston (BOS)

View CA $150 flight on Wed, Sep 16, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at CA $150 for one-way flights and CA $300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Thu, Oct 22 - Wed, Oct 28
ORD
Chicago
BOS
Boston
CA $300 Roundtrip, found 7 hours ago
CA $300
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Thu, Oct 22 from Chicago to Boston, returning Wed, Oct 28, priced at CA $300 found 7 hours ago
Delta
Sat, Sep 19 - Mon, Sep 21
ORD
Chicago
BOS
Boston
CA $300 Roundtrip, found 7 hours ago
CA $300
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, Sep 19 from Chicago to Boston, returning Mon, Sep 21, priced at CA $300 found 7 hours ago
American Airlines
Sat, Sep 19 - Mon, Sep 21
ORD
Chicago
BOS
Boston
CA $301 Roundtrip, found 7 hours ago
CA $301
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Sep 19 from Chicago to Boston, returning Mon, Sep 21, priced at CA $301 found 7 hours ago
American Airlines
Fri, Oct 23 - Mon, Oct 26
ORD
Chicago
BOS
Boston
CA $313 Roundtrip, found 7 hours ago
CA $313
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Oct 23 from Chicago to Boston, returning Mon, Oct 26, priced at CA $313 found 7 hours ago
American Airlines
Fri, Sep 18 - Fri, Sep 25
ORD
Chicago
BOS
Boston
CA $325 Roundtrip, just found
CA $325
Roundtrip
just found
Select American Airlines flight, departing Fri, Sep 18 from Chicago to Boston, returning Fri, Sep 25, priced at CA $325 just found
American Airlines
Fri, Sep 18 - Fri, Sep 25
ORD
Chicago
BOS
Boston
CA $326 Roundtrip, just found
CA $326
Roundtrip
just found
Select American Airlines flight, departing Fri, Sep 18 from Chicago to Boston, returning Fri, Sep 25, priced at CA $326 just found
American Airlines
Fri, Oct 23 - Mon, Oct 26
ORD
Chicago
BOS
Boston
CA $326 Roundtrip, found 7 hours ago
CA $326
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Oct 23 from Chicago to Boston, returning Mon, Oct 26, priced at CA $326 found 7 hours ago
American Airlines
Fri, Sep 18 - Mon, Sep 21
ORD
Chicago
BOS
Boston
CA $338 Roundtrip, found 12 hours ago
CA $338
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Fri, Sep 18 from Chicago to Boston, returning Mon, Sep 21, priced at CA $338 found 12 hours ago
United
Sat, Sep 19 - Mon, Sep 21
ORD
Chicago
BOS
Boston
CA $411 Roundtrip, found 7 hours ago
CA $411
Roundtrip
found 7 hours ago
Select United flight, departing Sat, Sep 19 from Chicago to Boston, returning Mon, Sep 21, priced at CA $411 found 7 hours ago
Alaska Airlines
Fri, Sep 25 - Tue, Sep 29
ORD
Chicago
BOS
Boston
CA $786 Roundtrip, found 10 hours ago
CA $786
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Fri, Sep 25 from Chicago to Boston, returning Tue, Sep 29, priced at CA $786 found 10 hours ago

Alternative airports near Boston

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BOS. Cheapest and Closest option available. Average driving time to city centre is 7 minutes. Flights from CA $341
BOS
Logan Intl.
CheapestClosest
Average driving time to city centre7 min
Flights from CA $341

Frequently asked questions

How much does a flight from Chicago, IL (ORD) to Boston, MA (BOS) cost?
You can find cheap one-way flights from CA $150 and cheap return flights from CA $300 ORD to BOS with Expedia. One-way flights typically cost between CA$188 and CA$551. 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.
What is the cheapest month to fly from Chicago, IL (ORD) to Boston, MA (BOS)?
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.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
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.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan 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 Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
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.
What is the best time to fly from Chicago, IL (ORD) to Boston, MA (BOS)?
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.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
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).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
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.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
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.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
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.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
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.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
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.
How do I earn miles on a Chicago, IL (ORD) to Boston, MA (BOS) flight with Expedia?
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.
What airports do you fly into for Boston, MA (BOS) from Chicago, IL (ORD)?
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.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD) to Boston, MA (BOS) at the last minute?
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.
Is it cheaper to book a Chicago, IL (ORD) to Boston, MA (BOS) flight and hotel package?
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.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Boston, MA (BOS-Logan 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
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, JetBlue Airways, United
Roundtrip price
CA $299
Distance
1381 km
Average flight time
3 hours 29 mins

Book with confidence

Chicago to Boston Flights

The easy way to book your flights from Chicago to Boston 

With Expedia, it’s simple to find and book flights to Boston from Chicago whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Logan Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Chicago to Boston today, tomorrow, or this week.  

 

Save dollars with cheap flights from O'Hare Intl., ORD to Logan Intl., BOS 

Sort your search results by price to find great deals on your flight from Chicago to Boston—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Boston from Chicago currently is just CA $300 rising to CA $786.  

Here are more money-saving tips: 

  • Fly in October when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Boston  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Boston from Chicago 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Boston with Expedia today.

Chicago to Boston Flights

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