Delta flights to Chicago from Boston

View S$120 flight on Tue, 2 Jun, 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$120 for one-way flights and S$252 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 6 Jun - Mon, 8 Jun
BOS
Boston
ORD
Chicago
S$252 Return, found 4 days ago
S$252
Return
found 4 days ago
Select Delta flight, departing Sat, 6 Jun from Boston to Chicago, returning Mon, 8 Jun, priced at S$252 found 4 days ago
Delta
Sat, 6 Jun - Sat, 25 Jul
BOS
Boston
ORD
Chicago
S$253 Return, found 1 day ago
S$253
Return
found 1 day ago
Select Delta flight, departing Sat, 6 Jun from Boston to Chicago, returning Sat, 25 Jul, priced at S$253 found 1 day ago
Delta
Fri, 5 Jun - Fri, 12 Jun
BOS
Boston
ORD
Chicago
S$257 Return, found 6 days ago
S$257
Return
found 6 days ago
Select Delta flight, departing Fri, 5 Jun from Boston to Chicago, returning Fri, 12 Jun, priced at S$257 found 6 days ago
Delta
Sat, 19 Sept - Mon, 21 Sept
BOS
Boston
ORD
Chicago
S$263 Return, found 5 days ago
S$263
Return
found 5 days ago
Select Delta flight, departing Sat, 19 Sept from Boston to Chicago, returning Mon, 21 Sept, priced at S$263 found 5 days ago
Delta
Sat, 6 Jun - Sat, 25 Jul
BOS
Boston
ORD
Chicago
S$266 Return, found 1 day ago
S$266
Return
found 1 day ago
Select Delta flight, departing Sat, 6 Jun from Boston to Chicago, returning Sat, 25 Jul, priced at S$266 found 1 day ago
Delta
Fri, 3 Jul - Sun, 5 Jul
BOS
Boston
ORD
Chicago
S$271 Return, found 2 days ago
S$271
Return
found 2 days ago
Select Delta flight, departing Fri, 3 Jul from Boston to Chicago, returning Sun, 5 Jul, priced at S$271 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from S$402
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from S$402

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$252 from BOS to ORD. Affordable one-way options from S$120 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."

Travel 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 54 mins

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