Cheap Flights from Chicago to Eastern Massachusetts

View €60 flight on Wed, 8 Oct 2025Opens in a new window

Popular airlines from Chicago to Eastern Massachusetts

  • Delta

    Delta

  • American Airlines

    American Airlines

  • JetBlue Airways

    JetBlue Airways

  • United

    United

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 15% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap flights from Chicago to Eastern Massachusetts (CHI-BOS)

Prices were available within the past 7 days and start at €60 for one-way flights and €118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sun, 24 Aug - Mon, 25 Aug
ORD
Chicago
BOS
Boston
€118 Return, found 1 hour ago
€118
Return
found 1 hour ago
Select American Airlines flight, departing Sun, 24 Aug from Chicago to Boston, returning Mon, 25 Aug, priced at €118 found 1 hour ago
JetBlue Airways
Tue, 8 Jul - Wed, 9 Jul
ORD
Chicago
BOS
Boston
€118 Return, found 3 hours ago
€118
Return
found 3 hours ago
Select JetBlue Airways flight, departing Tue, 8 Jul from Chicago to Boston, returning Wed, 9 Jul, priced at €118 found 3 hours ago
Delta
Tue, 8 Jul - Wed, 9 Jul
ORD
Chicago
BOS
Boston
€118 Return, found 3 hours ago
€118
Return
found 3 hours ago
Select Delta flight, departing Tue, 8 Jul from Chicago to Boston, returning Wed, 9 Jul, priced at €118 found 3 hours ago
Delta
Tue, 8 Jul - Wed, 9 Jul
ORD
Chicago
BOS
Boston
€119 Return, found 3 hours ago
€119
Return
found 3 hours ago
Select Delta flight, departing Tue, 8 Jul from Chicago to Boston, returning Wed, 9 Jul, priced at €119 found 3 hours ago
Delta
Tue, 19 Aug - Sat, 30 Aug
ORD
Chicago
BOS
Boston
€121 Return, found 6 days ago
€121
Return
found 6 days ago
Select Delta flight, departing Tue, 19 Aug from Chicago to Boston, returning Sat, 30 Aug, priced at €121 found 6 days ago
United
Tue, 8 Jul - Wed, 9 Jul
ORD
Chicago
BOS
Boston
€178 Return, found 3 hours ago
€178
Return
found 3 hours ago
Select United flight, departing Tue, 8 Jul from Chicago to Boston, returning Wed, 9 Jul, priced at €178 found 3 hours ago

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

August is typically the cheapest month to fly

From €41 - €126 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.