$57 Cheap Flights from Chicago (ORD) to Boston (BOS)

View $57 flight on Wed, Nov 19, 2025Opens in a new window

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

Today's featured flight deals from Chicago O'Hare Intl. Airport (ORD) to Logan International Airport (BOS)

Nonstop
Carry-on included
Lower price than typical

Cheap Flights from Chicago to Boston (ORD-BOS)

Prices were available within the past 7 days and start at $57 for one-way flights and $66 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Fri, Jan 30 - Fri, Jan 30
ORD
Chicago
BOS
Boston
$66 Roundtrip, found 6 days ago
$66
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Fri, Jan 30 from Chicago to Boston, returning Fri, Jan 30, priced at $66 found 6 days ago
JetBlue Airways
Mon, Dec 15 - Mon, Dec 15
ORD
Chicago
BOS
Boston
$86 Roundtrip, found 5 days ago
$86
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Dec 15 from Chicago to Boston, returning Mon, Dec 15, priced at $86 found 5 days ago
Spirit Airlines
Wed, Nov 19 - Wed, Jan 28
ORD
Chicago
BOS
Boston
$106 Roundtrip, found 5 days ago
$106
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Nov 19 from Chicago to Boston, returning Wed, Jan 28, priced at $106 found 5 days ago
JetBlue Airways
Sat, Jan 17 - Sat, Jan 17
ORD
Chicago
BOS
Boston
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Jan 17 from Chicago to Boston, returning Sat, Jan 17, priced at $112 found 5 days ago
Delta
Fri, Dec 5 - Thu, Dec 11
ORD
Chicago
BOS
Boston
$114 Roundtrip, found 7 hours ago
$114
Roundtrip
found 7 hours ago
Select Delta flight, departing Fri, Dec 5 from Chicago to Boston, returning Thu, Dec 11, priced at $114 found 7 hours ago
American Airlines
Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select American Airlines flight, departing Sat, Jan 17 from Chicago to Boston, returning Tue, Jan 20, priced at $117 just found
Delta
Thu, Dec 4 - Sun, Dec 7
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Delta flight, departing Thu, Dec 4 from Chicago to Boston, returning Sun, Dec 7, priced at $117 just found
United
Fri, Dec 5 - Wed, Dec 10
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select United flight, departing Fri, Dec 5 from Chicago to Boston, returning Wed, Dec 10, priced at $117 just found
American Airlines
Sat, Jan 17 - Tue, Jan 20
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select American Airlines flight, departing Sat, Jan 17 from Chicago to Boston, returning Tue, Jan 20, priced at $117 just found
American Airlines
Mon, Nov 17 - Thu, Nov 20
ORD
Chicago
BOS
Boston
$119 Roundtrip, just found
$119
Roundtrip
just found
Select American Airlines flight, departing Mon, Nov 17 from Chicago to Boston, returning Thu, Nov 20, priced at $119 just found

Find the cheapest month to fly from Chicago (ORD) to Boston (BOS)

November is typically the cheapest month to fly

From $87 - $266 per traveler.

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 center is 7 minutes. Flights from $140
BOS
Logan Intl.
CheapestClosest
Average driving time to city center7 min
Flights from $140

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) cost?
Snag a cheap one-way flight from $57 or cheap return flight from $66 from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
Flying in January can help you save, as it's the cheapest month for flights between ORD and BOS. You'll often find the lowest fares during off-peak months.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
Select from 4 carriers that operate direct flights from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS). These include:

  • American Airlines
  • United Airlines
  • Delta Air Lines

What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
JetBlue Airways and Delta Air Lines are popular airlines offering competitive fares. Don't forget that flight prices from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) can vary based on travel dates, demand and how early you book. With Expedia's search tool, you can easily find a ORD to BOS flight that matches your preferences and budget.
How many flights per day from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
Each day on average, 16 nonstop flights take off from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS). Choose the departure time that best fits your itinerary.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
The 6 PM departures from ORD to BOS are typically the busiest. Greater demand means you'll likely pay more for these departures. If you want to save on your fare, pick a less crowded time to fly.
What day of the week has the most flights from ORD to BOS?
Fly on a Friday if you're looking for the best selection of flights from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
The earliest flight leaving from O'Hare Intl. Airport (ORD) is at around 6:00AM UTC-6. Catch this flight and you'll land at Logan Intl. Airport (BOS) at approximately 9:33AM UTC-5. The entire trip takes 2h 33m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
The average flight duration from ORD to BOS is 2 hours and 25 minutes, covering a distance of 860 mi.
What airline has the least delays from ORD to BOS?
With 100% of flights usually arriving as scheduled, LATAM Airlines has the best on-time performance for nonstop flights from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS). To monitor your flight status and get notifications about any changes, head to the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
Book a flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) that takes off before 3 PM to reduce the likelihood of delays. Departures later than this are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Boston from O'Hare Intl. Airport (ORD)?
You'll land at Logan Intl. Airport (BOS) or T.F. Green Airport (PVD) when traveling to Boston on a direct flight from O'Hare Intl. Airport (ORD).
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) last-minute?
Holding off until just before your departure to book your flight from ORD to BOS generally means paying more. While you may come across some last-minute deals, there's no guarantee. Be flexible with your itinerary to boost your chances of getting a bargain.
Is it cheaper to book an ORD to BOS flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to BOS flight and hotel package with Expedia could result in significant savings. Better still, having everything in one easy place will take the hassle out of travel planning. Just pick your flights and choose from our extensive range of hotels, then tailor your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
In most cases, you can modify or cancel your ORD to BOS flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's fees and guidelines on flight changes, or if you need more details, visit our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$65
Distance
863 mi
Average flight time
3 hours 19 mins

Book with confidence

Chicago to Boston Flights

The cheapest times to fly from Chicago to Boston

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 Chicago to Boston are during the month of January. You can find some of the cheapest flights from Chicago to Boston with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Boston

Sunday is one of the best days to book for cheap flights from Chicago to Boston: 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 Chicago to Boston

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 Chicago to Boston in 2025. You can also book with separate airlines for your outbound and return journeys, from $57 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 Chicago to Boston 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 Chicago to Boston 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.

 

Chicago to Boston Flights

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*Available to One Key members.