S$89 Cheap Flights from Chicago to Boston

View S$89 flight on Tue, 30 Sep, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Logan International Airport (BOS)

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Cheap Flights from Chicago to Boston (ORD-BOS)

Prices were available within the past 7 days and start at S$89 for one-way flights and S$152 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 4 Sep - Wed, 10 Sep
ORD
Chicago
BOS
Boston
S$152 Return, found 6 days ago
S$152
Return
found 6 days ago
Select Delta flight, departing Thu, 4 Sep from Chicago to Boston, returning Wed, 10 Sep, priced at S$152 found 6 days ago
Delta
Tue, 21 Oct - Tue, 4 Nov
ORD
Chicago
BOS
Boston
S$176 Return, found 1 day ago
S$176
Return
found 1 day ago
Select Delta flight, departing Tue, 21 Oct from Chicago to Boston, returning Tue, 4 Nov, priced at S$176 found 1 day ago
Delta
Thu, 4 Sep - Wed, 10 Sep
ORD
Chicago
BOS
Boston
S$189 Return, found 6 days ago
S$189
Return
found 6 days ago
Select Delta flight, departing Thu, 4 Sep from Chicago to Boston, returning Wed, 10 Sep, priced at S$189 found 6 days ago
United
Thu, 4 Sep - Wed, 10 Sep
ORD
Chicago
BOS
Boston
S$190 Return, found 6 days ago
S$190
Return
found 6 days ago
Select United flight, departing Thu, 4 Sep from Chicago to Boston, returning Wed, 10 Sep, priced at S$190 found 6 days ago
Delta
Tue, 28 Oct - Thu, 30 Oct
ORD
Chicago
BOS
Boston
S$202 Return, found 11 hours ago
S$202
Return
found 11 hours ago
Select Delta flight, departing Tue, 28 Oct from Chicago to Boston, returning Thu, 30 Oct, priced at S$202 found 11 hours ago
Delta
Tue, 28 Oct - Thu, 30 Oct
ORD
Chicago
BOS
Boston
S$223 Return, found 11 hours ago
S$223
Return
found 11 hours ago
Select Delta flight, departing Tue, 28 Oct from Chicago to Boston, returning Thu, 30 Oct, priced at S$223 found 11 hours ago
American Airlines
Thu, 4 Sep - Wed, 10 Sep
ORD
Chicago
BOS
Boston
S$228 Return, found 6 days ago
S$228
Return
found 6 days ago
Select American Airlines flight, departing Thu, 4 Sep from Chicago to Boston, returning Wed, 10 Sep, priced at S$228 found 6 days ago
United
Thu, 4 Sep - Wed, 10 Sep
ORD
Chicago
BOS
Boston
S$228 Return, found 6 days ago
S$228
Return
found 6 days ago
Select United flight, departing Thu, 4 Sep from Chicago to Boston, returning Wed, 10 Sep, priced at S$228 found 6 days ago
Delta
Thu, 4 Sep - Wed, 10 Sep
ORD
Chicago
BOS
Boston
S$229 Return, found 6 days ago
S$229
Return
found 6 days ago
Select Delta flight, departing Thu, 4 Sep from Chicago to Boston, returning Wed, 10 Sep, priced at S$229 found 6 days ago
JetBlue Airways
Fri, 19 Sep - Tue, 30 Sep
ORD
Chicago
BOS
Boston
S$254 Return, found 1 day ago
S$254
Return
found 1 day ago
Select JetBlue Airways flight, departing Fri, 19 Sep from Chicago to Boston, returning Tue, 30 Sep, priced at S$254 found 1 day ago

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

November is typically the cheapest month to fly

From S$72 - S$354 per traveller.

Graph displaying average flight prices per month

Chicago to Boston route information
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, United
Return price
S$151
Distance
1381 km
Average flight time
3 hours 24 mins

Flights from Chicago to Boston

There are several airlines that operate frequent flights from Chicago (ORD) to Boston (BOS) including

The earliest flight leaves O'Hare Intl. Airport at 06:00 and arrives at Logan Intl. Airport at 00:14. The last flight of the day departs Chicago at 22:00 and arrives at Boston at 23:46.

The flight distance from Chicago to Boston is about 1398 km, the shortest flight is 02 hours 10 minutes with Air Europa.

Expedia lets you search across the largest number of airlines and Boston flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chicago Boston flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago to Boston trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Boston flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Chicago to Boston with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
Start packing your suitcase, because round-trip flights from ORD to Logan Intl. Airport (BOS) start from S$152. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to score the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to BOS?
Most flights can be cancelled online, but every air carrier has different terms and conditions. If you do need to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from ORD to Logan Intl. Airport 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 O'Hare Airport to Logan Intl. Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to Logan Intl. Airport?
That new movie you've been desperate to see will just have to wait — the flight distance between O'Hare Airport (ORD) and BOS (BOS) is only 1,400 kilometres. The captain will be asking you to put your seat upright for landing before you know it.
Which airlines fly direct from ORD to Logan Intl. Airport (BOS)?
It's easy to fly directly from O'Hare Intl. Airport (ORD) to Logan Intl. Airport. Here are some of the top carriers that offer nonstop services on this route:

  • American Airlines - (AA) with 225 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 O'Hare Intl. Airport (ORD) to Logan Intl. Airport flight tickets cheaper when they're purchased at the last minute?
It is possible to score an awesome last-minute deal from ORD to BOS, but there's no guarantee. As many airlines release seats up to a year in advance, it's worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals regularly, so you can be certain you're always seeing the latest offers.

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