Delta flights to Chicago from Boston

View S$90 flight on Wed, 18 Mar, 2026Opens in a new window
  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Delta flights from Boston to Chicago (BOS→ORD)

Prices were available within the past 7 days and start at S$90 for one-way flights and S$319 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 18 Dec - Thu, 25 Dec
BOS
Boston
ORD
Chicago
S$319 Return, found 17 hours ago
S$319
Return
found 17 hours ago
Select Delta flight, departing Thu, 18 Dec from Boston to Chicago, returning Thu, 25 Dec, priced at S$319 found 17 hours ago
Delta
Thu, 18 Dec - Thu, 25 Dec
BOS
Boston
ORD
Chicago
S$332 Return, found 17 hours ago
S$332
Return
found 17 hours ago
Select Delta flight, departing Thu, 18 Dec from Boston to Chicago, returning Thu, 25 Dec, priced at S$332 found 17 hours ago
Delta
Thu, 18 Dec - Thu, 25 Dec
BOS
Boston
ORD
Chicago
S$340 Return, found 17 hours ago
S$340
Return
found 17 hours ago
Select Delta flight, departing Thu, 18 Dec from Boston to Chicago, returning Thu, 25 Dec, priced at S$340 found 17 hours ago
Delta
Thu, 18 Dec - Thu, 25 Dec
BOS
Boston
ORD
Chicago
S$353 Return, found 17 hours ago
S$353
Return
found 17 hours ago
Select Delta flight, departing Thu, 18 Dec from Boston to Chicago, returning Thu, 25 Dec, priced at S$353 found 17 hours ago
Delta
Thu, 18 Dec - Thu, 25 Dec
BOS
Boston
ORD
Chicago
S$365 Return, found 17 hours ago
S$365
Return
found 17 hours ago
Select Delta flight, departing Thu, 18 Dec from Boston to Chicago, returning Thu, 25 Dec, priced at S$365 found 17 hours ago
Delta
Thu, 18 Dec - Thu, 25 Dec
BOS
Boston
ORD
Chicago
S$374 Return, found 17 hours ago
S$374
Return
found 17 hours ago
Select Delta flight, departing Thu, 18 Dec from Boston to Chicago, returning Thu, 25 Dec, priced at S$374 found 17 hours 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$210 per traveller.
Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Popular airline
American Airlines
Distance
1381 km
Average flight time
1 hour 58 mins

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$319 from BOS to ORD. Affordable one-way options from S$90 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."
*Available to Expedia members.