Cheap Flights from Boston to Central United States

View €41 flight on Sat, 7 Feb 2026Opens in a new window

Popular airlines from Boston to Central United States

  • Spirit Airlines

    Spirit Airlines

  • JetBlue Airways

    JetBlue Airways

  • American Airlines

    American Airlines

  • United

    United

  • Delta

    Delta

  • Southwest Airlines

    Southwest Airlines

  • Frontier Airlines

    Frontier Airlines

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Cheap flights from Boston to Central United States (BOS-CHI)

Prices were available within the past 7 days and start at €41 for one-way flights and €80 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, 29 Oct - Mon, 3 Nov
BOS
Boston
ORD
Chicago
€80 Return, found 6 days ago
€80
Return
found 6 days ago
Select American Airlines flight, departing Wed, 29 Oct from Boston to Chicago, returning Mon, 3 Nov, priced at €80 found 6 days ago
JetBlue Airways
Wed, 29 Oct - Mon, 3 Nov
BOS
Boston
ORD
Chicago
€80 Return, found 6 days ago
€80
Return
found 6 days ago
Select JetBlue Airways flight, departing Wed, 29 Oct from Boston to Chicago, returning Mon, 3 Nov, priced at €80 found 6 days ago
JetBlue Airways
Tue, 28 Oct - Mon, 3 Nov
BOS
Boston
ORD
Chicago
€86 Return, found 21 hours ago
€86
Return
found 21 hours ago
Select JetBlue Airways flight, departing Tue, 28 Oct from Boston to Chicago, returning Mon, 3 Nov, priced at €86 found 21 hours ago
Delta
Wed, 29 Oct - Mon, 3 Nov
BOS
Boston
ORD
Chicago
€100 Return, found 6 days ago
€100
Return
found 6 days ago
Select Delta flight, departing Wed, 29 Oct from Boston to Chicago, returning Mon, 3 Nov, priced at €100 found 6 days ago
United
Thu, 4 Sep - Sun, 7 Sep
BOS
Boston
ORD
Chicago
€146 Return, found 2 hours ago
€146
Return
found 2 hours ago
Select United flight, departing Thu, 4 Sep from Boston to Chicago, returning Sun, 7 Sep, priced at €146 found 2 hours ago
Cape Air
Thu, 13 Nov - Tue, 18 Nov
EWB
New Bedford
IAH
Houston
€413 Return, found 7 hours ago
€413
Return
found 7 hours ago
Select Cape Air flight, departing Thu, 13 Nov from New Bedford to Houston, returning Tue, 18 Nov, priced at €413 found 7 hours ago

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

September is typically the cheapest month to fly

From €48 - €98 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.