Delta flights to Chicago from Boston

View S$75 flight on Sat, 9 May, 2026Opens in a new window

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Delta flights from Boston to Chicago (BOS→ORD)

Prices were available within the past 7 days and start at S$75 for one-way flights and S$149 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$149 Return, found 3 days ago
S$149
Return
found 3 days ago
Select Delta flight, departing Sat, 25 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$149 found 3 days ago
Delta
Wed, 1 Apr - Tue, 21 Apr
BOS
Boston
ORD
Chicago
S$155 Return, found 3 days ago
S$155
Return
found 3 days ago
Select Delta flight, departing Wed, 1 Apr from Boston to Chicago, returning Tue, 21 Apr, priced at S$155 found 3 days ago
Delta
Wed, 27 May - Tue, 16 Jun
BOS
Boston
ORD
Chicago
S$166 Return, found 3 days ago
S$166
Return
found 3 days ago
Select Delta flight, departing Wed, 27 May from Boston to Chicago, returning Tue, 16 Jun, priced at S$166 found 3 days ago
Delta
Sat, 25 Apr - Fri, 8 May
BOS
Boston
ORD
Chicago
S$174 Return, found 3 days ago
S$174
Return
found 3 days ago
Select Delta flight, departing Sat, 25 Apr from Boston to Chicago, returning Fri, 8 May, priced at S$174 found 3 days ago
Delta
Wed, 1 Apr - Mon, 20 Apr
BOS
Boston
ORD
Chicago
S$180 Return, found 3 days ago
S$180
Return
found 3 days ago
Select Delta flight, departing Wed, 1 Apr from Boston to Chicago, returning Mon, 20 Apr, priced at S$180 found 3 days ago
Delta
Fri, 24 Apr - Sat, 9 May
BOS
Boston
ORD
Chicago
S$200 Return, found 3 days ago
S$200
Return
found 3 days ago
Select Delta flight, departing Fri, 24 Apr from Boston to Chicago, returning Sat, 9 May, priced at S$200 found 3 days ago

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

January is typically the cheapest month to fly

From S$118 - S$206 per traveller.

Frequently asked questions

How much is a Delta Air Lines flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Use the "Price (lowest to highest)" filter on Expedia to find cheap Delta Air Lines return flights from S$149 from BOS to ORD. Affordable one-way options from S$75 are available too.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from BOS to ORD with Delta Air Lines?
Delta Air Lines flights to Chicago are usually cheaper in the quieter months of January and February. Whether you're after a one-way or a return ticket, you could land a better deal then.
Does Delta Air Lines fly nonstop from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Take off on one of Delta Air Lines's 27 direct weekly flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD). To see what's available, enter your travel dates, origin and destination and hit search. Then select the "Nonstop" and "Airline" filters.
How long does it take to fly from BOS to ORD with Delta Air Lines?
Take off from Logan Intl. Airport (BOS) for O'Hare Intl. Airport (ORD) on a nonstop Delta Air Lines flight, and you'll be in the air for about 3h 2m.
Which day of the week has the most Delta Air Lines flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Delta Air Lines operates the most flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD) on Saturday. With up to 4 daily departures, you'll get the most flexibility and choice on this day.
What airports does Delta Air Lines fly into in Chicago?
The majority of Delta Air Lines flights from Logan Intl. Airport (BOS) to Chicago land at O'Hare Intl. Airport (ORD). This is the airline's main point of entry here. It's also worth browsing Expedia for flights to nearby airports like Midway Intl. Airport (MDW), as prices may be cheaper.
What type of plane does Delta Air Lines fly from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Take a Delta Air Lines flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD), and you'll likely be flying on an Embraer 175. Keep in mind though, that the aircraft type can change due to operational requirements.
Can I change or cancel my Delta Air Lines flight from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)?
Depending on the ticket type you purchased, a fee may apply if you cancel or reschedule your booking more than 24 hours after it's confirmed. To secure plane tickets with more flexibility, select our "Changes included" and "No cancel fee" boxes when you search for flights. To learn more about cancelling or modifying your reservation, visit "Trips," select your flight and tick "Manage Booking."

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Travel information

Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Popular airline
Delta
Distance
1381 km
Average flight time
2 hours 4 mins

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