S$108 Cheap Flights from Boston to Chicago

View S$108 flight on Sat, 2 May, 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 S$108 for one-way flights and S$254 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$254 Return, found 3 days ago
S$254
Return
found 3 days ago
Select Delta flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$254 found 3 days ago
Delta
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$286 Return, found 3 days ago
S$286
Return
found 3 days ago
Select Delta flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$286 found 3 days ago
American Airlines
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$288 Return, found 3 days ago
S$288
Return
found 3 days ago
Select American Airlines flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$288 found 3 days ago
United
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$306 Return, found 3 days ago
S$306
Return
found 3 days ago
Select United flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$306 found 3 days ago
Delta
Thu, 15 Oct - Sun, 18 Oct
BOS
Boston
ORD
Chicago
S$314 Return, found 2 days ago
S$314
Return
found 2 days ago
Select Delta flight, departing Thu, 15 Oct from Boston to Chicago, returning Sun, 18 Oct, priced at S$314 found 2 days ago
United
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$319 Return, found 3 days ago
S$319
Return
found 3 days ago
Select United flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$319 found 3 days ago
American Airlines
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$319 Return, found 3 days ago
S$319
Return
found 3 days ago
Select American Airlines flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$319 found 3 days ago
Delta
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$336 Return, found 3 days ago
S$336
Return
found 3 days ago
Select Delta flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$336 found 3 days ago
Delta
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$338 Return, found 3 days ago
S$338
Return
found 3 days ago
Select Delta flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$338 found 3 days ago
American Airlines
Sat, 25 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$342 Return, found 3 days ago
S$342
Return
found 3 days ago
Select American Airlines flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$342 found 3 days ago

Frequently asked questions

How much is a flight from Logan Intl. Airport to ORD?
If you're planning on travelling from BOS to O'Hare Airport, round-trip flights start from S$254. This price is based on airfares advertised within the last 7 days on Expedia for flights departing within the next year, so don't hang about. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport (BOS) to ORD?
The majority of flights can be conveniently cancelled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from BOS to O'Hare Intl. Airport (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 Logan Intl. Airport to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from BOS to O'Hare Intl. Airport (ORD)?
Forget about a movie marathon on this flight — it's only 1,400 kilometres from Boston to Chicago. Sit down, buckle up and you'll be touching down before long.
Which airlines fly direct from Logan Intl. Airport to ORD?
It's a breeze to fly directly from Logan Intl. Airport to ORD. Below are some of the top carriers that operate nonstop services on this route:

  • American Airlines - (AA) with 230 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 Logan Intl. Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
It is possible to get great last-minute deals from BOS to O'Hare Airport, but it's also possible to miss out entirely! As many airlines publish prices up to a year in advance, it's worth keeping an eye on fares early and being ready to pounce when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can rest easy knowing you're always getting the latest offers.

Travel information

Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
S$254
Distance
1381 km
Average flight time
1 hour 58 mins

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