฿2,155 Cheap Flights from Chicago (ORD) to Boston (BOS)

View ฿2,155 flight on Sat, 17 Jan 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at ฿2,155 for one-way flights and ฿4,300 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 17 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿4,300 Return, found 2 hours ago
฿4,300
Return
found 2 hours ago
Select Delta flight, departing Sat, 17 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿4,300 found 2 hours ago
Delta
Mon, 16 Mar - Fri, 20 Mar
ORD
Chicago
BOS
Boston
฿5,240 Return, found 12 hours ago
฿5,240
Return
found 12 hours ago
Select Delta flight, departing Mon, 16 Mar from Chicago to Boston, returning Fri, 20 Mar, priced at ฿5,240 found 12 hours ago
United
Sat, 17 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿5,245 Return, found 2 hours ago
฿5,245
Return
found 2 hours ago
Select United flight, departing Sat, 17 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿5,245 found 2 hours ago
Delta
Sat, 17 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿5,265 Return, found 2 hours ago
฿5,265
Return
found 2 hours ago
Select Delta flight, departing Sat, 17 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿5,265 found 2 hours ago
Delta
Thu, 15 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿5,605 Return, found 6 days ago
฿5,605
Return
found 6 days ago
Select Delta flight, departing Thu, 15 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿5,605 found 6 days ago
United
Thu, 15 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿5,770 Return, found 6 days ago
฿5,770
Return
found 6 days ago
Select United flight, departing Thu, 15 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿5,770 found 6 days ago
United
Thu, 15 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿5,925 Return, found 6 days ago
฿5,925
Return
found 6 days ago
Select United flight, departing Thu, 15 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿5,925 found 6 days ago
United
Thu, 15 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿5,930 Return, found 6 days ago
฿5,930
Return
found 6 days ago
Select United flight, departing Thu, 15 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿5,930 found 6 days ago
Delta
Sat, 17 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿6,025 Return, found 2 hours ago
฿6,025
Return
found 2 hours ago
Select Delta flight, departing Sat, 17 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿6,025 found 2 hours ago
American Airlines
Sat, 17 Jan - Sun, 18 Jan
ORD
Chicago
BOS
Boston
฿6,175 Return, found 2 hours ago
฿6,175
Return
found 2 hours ago
Select American Airlines flight, departing Sat, 17 Jan from Chicago to Boston, returning Sun, 18 Jan, priced at ฿6,175 found 2 hours ago

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

January is typically the cheapest month to fly

From ฿2,913 - ฿5,026 per traveller.
Flight from Chicago to Boston route information
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, United
Return price
฿4,300
Distance
1381 km
Average flight time
3 hours 22 mins

Perfect flights from Chicago to Boston

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Boston. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible O'Hare Intl. to Logan Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿2,155 and roundtrip prices from ฿4,300. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Logan Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Boston.

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
Start packing your suitcase, because round-trip flights from ORD to Logan Intl. Airport (BOS) start from ฿4,300. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to score the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to BOS?
Most flights can be cancelled online, but every air carrier has different terms and conditions. If you do need to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from ORD to Logan Intl. Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for O'Hare Airport to Logan Intl. Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to Logan Intl. Airport?
That new movie you've been desperate to see will just have to wait — the flight distance between O'Hare Airport (ORD) and BOS (BOS) is only 1,400 kilometres. The captain will be asking you to put your seat upright for landing before you know it.
Which airlines fly direct from ORD to Logan Intl. Airport (BOS)?
It's easy to fly directly from O'Hare Intl. Airport (ORD) to Logan Intl. Airport. Here are some of the top carriers that offer nonstop services on this route:

  • American Airlines - (AA) with 225 monthly flights
  • United Airlines - (UA) with 178 monthly flights
  • Delta Air Lines - (DL) with 139 monthly flights
  • JetBlue Airways - (B6) with 30 monthly flights

Are O'Hare Intl. Airport (ORD) to Logan Intl. Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to score an awesome last-minute deal from ORD to BOS, but there's no guarantee. As many airlines release seats up to a year in advance, it's worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals regularly, so you can be certain you're always seeing the latest offers.
*Available to Expedia members.