S$101 Cheap Flights from Chicago to Boston

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Cheap Flights from Chicago to Boston (ORD-BOS)

Prices were available within the past 7 days and start at S$101 for one-way flights and S$234 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 29 May - Wed, 5 Jun
ORD
Chicago
BOS
Boston
S$234 Return, found 1 day ago
S$234
Return
found 1 day ago
Select Delta flight, departing Wed, 29 May from Chicago to Boston, returning Wed, 5 Jun, priced at S$234 found 1 day ago
Delta
Wed, 29 May - Thu, 6 Jun
ORD
Chicago
BOS
Boston
S$243 Return, found 1 day ago
S$243
Return
found 1 day ago
Select Delta flight, departing Wed, 29 May from Chicago to Boston, returning Thu, 6 Jun, priced at S$243 found 1 day ago
Delta
Sat, 11 May - Wed, 15 May
ORD
Chicago
BOS
Boston
S$244 Return, found 3 days ago
S$244
Return
found 3 days ago
Select Delta flight, departing Sat, 11 May from Chicago to Boston, returning Wed, 15 May, priced at S$244 found 3 days ago
Delta
Wed, 29 May - Wed, 5 Jun
ORD
Chicago
BOS
Boston
S$262 Return, found 1 day ago
S$262
Return
found 1 day ago
Select Delta flight, departing Wed, 29 May from Chicago to Boston, returning Wed, 5 Jun, priced at S$262 found 1 day ago
Delta
Sat, 11 May - Wed, 15 May
ORD
Chicago
BOS
Boston
S$264 Return, found 3 days ago
S$264
Return
found 3 days ago
Select Delta flight, departing Sat, 11 May from Chicago to Boston, returning Wed, 15 May, priced at S$264 found 3 days ago
United
Wed, 29 May - Wed, 5 Jun
ORD
Chicago
BOS
Boston
S$268 Return, found 1 day ago
S$268
Return
found 1 day ago
Select United flight, departing Wed, 29 May from Chicago to Boston, returning Wed, 5 Jun, priced at S$268 found 1 day ago
Delta
Wed, 29 May - Wed, 5 Jun
ORD
Chicago
BOS
Boston
S$269 Return, found 1 day ago
S$269
Return
found 1 day ago
Select Delta flight, departing Wed, 29 May from Chicago to Boston, returning Wed, 5 Jun, priced at S$269 found 1 day ago
Delta
Wed, 29 May - Thu, 6 Jun
ORD
Chicago
BOS
Boston
S$276 Return, found 1 day ago
S$276
Return
found 1 day ago
Select Delta flight, departing Wed, 29 May from Chicago to Boston, returning Thu, 6 Jun, priced at S$276 found 1 day ago
Delta
Fri, 12 Jul - Mon, 15 Jul
ORD
Chicago
BOS
Boston
S$291 Return, just found
S$291
Return
just found
Select Delta flight, departing Fri, 12 Jul from Chicago to Boston, returning Mon, 15 Jul, priced at S$291 just found
United
Wed, 29 May - Wed, 5 Jun
ORD
Chicago
BOS
Boston
S$296 Return, found 1 day ago
S$296
Return
found 1 day ago
Select United flight, departing Wed, 29 May from Chicago to Boston, returning Wed, 5 Jun, priced at S$296 found 1 day ago
Chicago to Boston route information
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$234
Distance
1381 km
Average flight time
3 hours 21 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$234. 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.
*Available to Expedia members.