￥9,040 Cheap Flights from Boston (BOS) to Chicago (ORD)

View ￥9,040 flight on Thu, Dec 11, 2025Opens 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 ￥9,040 for one-way flights and ￥18,070 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Dec 4 - Wed, Dec 10
BOS
Boston
ORD
Chicago
￥18,070 Roundtrip, found 4 days ago
￥18,070
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Dec 4 from Boston to Chicago, returning Wed, Dec 10, priced at ￥18,070 found 4 days ago
Delta
Thu, Dec 4 - Wed, Dec 10
BOS
Boston
ORD
Chicago
￥18,080 Roundtrip, found 4 days ago
￥18,080
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Dec 4 from Boston to Chicago, returning Wed, Dec 10, priced at ￥18,080 found 4 days ago
American Airlines
Thu, Dec 4 - Sat, Dec 13
BOS
Boston
ORD
Chicago
￥18,090 Roundtrip, found 3 days ago
￥18,090
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 4 from Boston to Chicago, returning Sat, Dec 13, priced at ￥18,090 found 3 days ago
Delta
Thu, Dec 4 - Sat, Dec 13
BOS
Boston
ORD
Chicago
￥18,100 Roundtrip, found 3 days ago
￥18,100
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 4 from Boston to Chicago, returning Sat, Dec 13, priced at ￥18,100 found 3 days ago
American Airlines
Thu, Dec 4 - Sun, Dec 7
BOS
Boston
ORD
Chicago
￥18,960 Roundtrip, found 2 days ago
￥18,960
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Dec 4 from Boston to Chicago, returning Sun, Dec 7, priced at ￥18,960 found 2 days ago
Delta
Thu, Dec 4 - Wed, Dec 10
BOS
Boston
ORD
Chicago
￥19,580 Roundtrip, found 4 days ago
￥19,580
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Dec 4 from Boston to Chicago, returning Wed, Dec 10, priced at ￥19,580 found 4 days ago
Delta
Thu, Dec 4 - Wed, Dec 10
BOS
Boston
ORD
Chicago
￥19,690 Roundtrip, found 4 days ago
￥19,690
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Dec 4 from Boston to Chicago, returning Wed, Dec 10, priced at ￥19,690 found 4 days ago
Delta
Thu, Dec 4 - Sat, Dec 13
BOS
Boston
ORD
Chicago
￥19,710 Roundtrip, found 3 days ago
￥19,710
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Dec 4 from Boston to Chicago, returning Sat, Dec 13, priced at ￥19,710 found 3 days ago
American Airlines
Thu, Dec 4 - Wed, Dec 10
BOS
Boston
ORD
Chicago
￥22,700 Roundtrip, found 4 days ago
￥22,700
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Dec 4 from Boston to Chicago, returning Wed, Dec 10, priced at ￥22,700 found 4 days ago
United
Thu, Dec 4 - Wed, Dec 10
BOS
Boston
ORD
Chicago
￥23,450 Roundtrip, found 4 days ago
￥23,450
Roundtrip
found 4 days ago
Select United flight, departing Thu, Dec 4 from Boston to Chicago, returning Wed, Dec 10, priced at ￥23,450 found 4 days ago

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

January is typically the cheapest month to fly

From ￥10,892 - ￥24,265 per traveler.

Frequently asked questions

How much is a flight from BOS to O'Hare Airport?
Start packing your bags, because round-trip journeys from Logan Intl. Airport to ORD start from ￥18,070. That's based on airfares available within the last 7 days on Expedia for flights departing within the next year. Prices can increase quickly, so book now to lock in 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 BOS to O'Hare Airport?
This can vary from airline to airline, as each one has its own terms and conditions. Head to the Customer Service Portal, where there are simple instructions on how to cancel your flight online.
How do I find cheap flights from BOS to ORD 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 BOS to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from BOS to O'Hare Airport?
It only takes an average of 2 hours and 52 minutes to journey from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD). Buckle up and make yourself comfortable — but not too comfortable. You'll be disembarking before long.
How far is the flight from Logan Intl. Airport to O'Hare Airport?
That new movie you've been desperate to see will just have to wait — the flight distance between Logan Intl. Airport (BOS) (BOS) and O'Hare Airport (ORD) is only 1,400 kilometers. The captain will be instructing you to put your seat upright for landing before you know it.
Which airlines fly direct from BOS to O'Hare Airport?
Check out the deals on offer with these popular carriers and book your ticket from Logan Intl. Airport to ORD today:

  • American Airlines - (AA) with 195 monthly flights
  • United Airlines - (UA) with 186 monthly flights
  • Delta Air Lines - (DL) with 121 monthly flights
  • JetBlue Airways - (B6) with 30 monthly flights

Are BOS to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Flight prices fluctuate, so there are no guarantees. While last-minute deals between BOS and O'Hare Airport are possible, it's also a good idea to keep a close eye on prices well before you fly. In fact, some carriers release their prices up to a year before the departure date. Expedia is constantly updating the biggest airfare bargains around, so check back often and be ready to book when the price is right.

Travel information

Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
￥18,070
Distance
1381 km
Average flight time
1 hour 58 mins

Book with confidence

Boston to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Boston to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with BOS to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Boston for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Boston to Chicago Flights

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T.F. Green to Chicago
￥51,400
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