NZ$114 Cheap Flights Chicago to Boston (CHI-BOS)

View NZ$114 flight on Mon, 25 Aug. 2025Opens in a new window

Popular airlines from Chicago to Boston, MA (BOS-Logan Intl.)

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Cheap Flights from Chicago (CHI) to Boston (BOS)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon., 25 Aug. - Sat., 30 Aug.
ORD
Chicago
BOS
Boston
NZ$228 Return, just found
NZ$228
Return
just found
Select Delta flight, departing Mon., 25 Aug. from Chicago to Boston, returning Sat., 30 Aug., priced at NZ$228 just found
American Airlines
Fri., 22 Aug. - Sun., 24 Aug.
ORD
Chicago
BOS
Boston
NZ$229 Return, found 4 days ago
NZ$229
Return
found 4 days ago
Select American Airlines flight, departing Fri., 22 Aug. from Chicago to Boston, returning Sun., 24 Aug., priced at NZ$229 found 4 days ago
Delta
Tue., 12 Aug. - Tue., 19 Aug.
ORD
Chicago
BOS
Boston
NZ$257 Return, found 2 days ago
NZ$257
Return
found 2 days ago
Select Delta flight, departing Tue., 12 Aug. from Chicago to Boston, returning Tue., 19 Aug., priced at NZ$257 found 2 days ago
American Airlines
Thu., 14 Aug. - Thu., 21 Aug.
ORD
Chicago
BOS
Boston
NZ$274 Return, found 20 hours ago
NZ$274
Return
found 20 hours ago
Select American Airlines flight, departing Thu., 14 Aug. from Chicago to Boston, returning Thu., 21 Aug., priced at NZ$274 found 20 hours ago
American Airlines
Fri., 22 Aug. - Sun., 24 Aug.
ORD
Chicago
BOS
Boston
NZ$275 Return, found 4 days ago
NZ$275
Return
found 4 days ago
Select American Airlines flight, departing Fri., 22 Aug. from Chicago to Boston, returning Sun., 24 Aug., priced at NZ$275 found 4 days ago
Delta
Sat., 23 Aug. - Sat., 30 Aug.
ORD
Chicago
BOS
Boston
NZ$277 Return, just found
NZ$277
Return
just found
Select Delta flight, departing Sat., 23 Aug. from Chicago to Boston, returning Sat., 30 Aug., priced at NZ$277 just found
Delta
Thu., 14 Aug. - Thu., 21 Aug.
ORD
Chicago
BOS
Boston
NZ$290 Return, found 20 hours ago
NZ$290
Return
found 20 hours ago
Select Delta flight, departing Thu., 14 Aug. from Chicago to Boston, returning Thu., 21 Aug., priced at NZ$290 found 20 hours ago
American Airlines
Mon., 25 Aug. - Sat., 13 Sep.
ORD
Chicago
BOS
Boston
NZ$293 Return, found 1 hour ago
NZ$293
Return
found 1 hour ago
Select American Airlines flight, departing Mon., 25 Aug. from Chicago to Boston, returning Sat., 13 Sep., priced at NZ$293 found 1 hour ago
JetBlue Airways
Mon., 25 Aug. - Mon., 1 Sep.
ORD
Chicago
BOS
Boston
NZ$326 Return, just found
NZ$326
Return
just found
Select JetBlue Airways flight, departing Mon., 25 Aug. from Chicago to Boston, returning Mon., 1 Sep., priced at NZ$326 just found
United
Thu., 28 Aug. - Fri., 29 Aug.
ORD
Chicago
BOS
Boston
NZ$343 Return, just found
NZ$343
Return
just found
Select United flight, departing Thu., 28 Aug. from Chicago to Boston, returning Fri., 29 Aug., priced at NZ$343 just found
Flight from Chicago to Boston route information
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, United
Return price
NZ$227
Distance
1381 km

CHI to BOS Flights

Ready to have the time of your life? When you use Expedia.co.nz to book cheap flights from Illinois to Boston, you can experience all of the attractions this city is famous for, or escape the crowds and explore the outskirts on your own. Our amazing deals on airfare help you save big on tickets, so you can spend more of your hard-earned money enjoying local entertainment options. Even if you seek to score a seat on one of the last-minute CHI to BOS flights, you’ll still save a bundle when compared to the competition.

See for yourself how simple it is to book the holiday of your dreams to Boston by using our helpful search engine today. We have the largest inventory of flights on the internet, and our intuitive tools make it easy to find affordable airfare at any time of year.

Prefer to fly with a particular airline? Our extensive network of travel partners ensures that you can travel with whichever carrier you prefer. So if you’ve been searching for cheap flights to Boston from Illinois, Expedia.co.nz has exactly what you’re looking for. As the world’s leader in travel, we’re committed to helping you get the best rates around.

Frequently asked questions

How much is a flight from Chicago, IL (CHI-All Airports) to BOS?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip flights from Chicago, IL (CHI-All Airports) to Logan Intl. Airport (BOS) start from NZ$228. Book now to score the best price for your trip. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Chicago, IL (CHI-All Airports) to Logan Intl. Airport (BOS)?
Every air carrier has its own terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from Chicago, IL (CHI-All Airports) to Logan Intl. Airport (BOS) 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 Chicago, IL (CHI-All Airports) to BOS flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Chicago, IL (CHI-All Airports) to BOS?
That new movie you've been wanting to see will have to wait --- the flight distance between Chicago, IL (CHI-All Airports) and Logan Intl. Airport (BOS) is only 1 450 kilometres. The captain will be telling you to buckle up for landing before you know it.
Which airlines fly direct from Chicago, IL (CHI-All Airports) to BOS?
You have plenty of choices when flying from Chicago, IL (CHI-All Airports) to BOS. Lock in your fare with one of these reputable carriers:

  • American Airlines - (AA) with 225 monthly flights
  • United Airlines - (UA) with 178 monthly flights
  • Delta Air Lines - (DL) with 139 monthly flights
  • Southwest Airlines - (WN) with 121 monthly flights

Are Chicago, IL (CHI-All Airports) to Logan Intl. Airport (BOS) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Chicago, IL (CHI-All Airports) to Logan Intl. Airport last minute could save you some cash. However, it could end up costing you a whole lot more! If you'd rather play it safe, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains as far ahead as 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time.

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Boston Flight Deals

Providence

Manchester

Provincetown

Chicago Airports

Chicago

O'Hare Intl. to Boston
NZ$227.10
Midway Intl. to Boston
NZ$524.90

Milwaukee

General Mitchell Intl. to Boston
NZ$483.20
*Available to Expedia members.