Cheap flights from Boston to South Suburbs

View AU$94 flight on Sat, 13 Sep. 2025Opens in a new window

Popular airlines from Boston to South Suburbs

  • American Airlines

    American Airlines

  • Delta

    Delta

  • United

    United

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Cheap Flights from Boston (BOS) to South Suburbs (CHI)

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.

American Airlines
Thu, 4 Sep. - Wed, 10 Sep.
BOS
Boston
ORD
Chicago
AU$183 Return, found 13 hours ago
AU$183
Return
found 13 hours ago
Select American Airlines flight, departing Thu, 4 Sep. from Boston to Chicago, returning Wed, 10 Sep., priced at AU$183 found 13 hours ago
Delta
Thu, 4 Sep. - Wed, 10 Sep.
BOS
Boston
ORD
Chicago
AU$211 Return, found 13 hours ago
AU$211
Return
found 13 hours ago
Select Delta flight, departing Thu, 4 Sep. from Boston to Chicago, returning Wed, 10 Sep., priced at AU$211 found 13 hours ago
American Airlines
Thu, 28 Aug. - Wed, 3 Sep.
BOS
Boston
ORD
Chicago
AU$213 Return, found 2 days ago
AU$213
Return
found 2 days ago
Select American Airlines flight, departing Thu, 28 Aug. from Boston to Chicago, returning Wed, 3 Sep., priced at AU$213 found 2 days ago
Delta
Thu, 4 Sep. - Wed, 10 Sep.
BOS
Boston
ORD
Chicago
AU$235 Return, found 13 hours ago
AU$235
Return
found 13 hours ago
Select Delta flight, departing Thu, 4 Sep. from Boston to Chicago, returning Wed, 10 Sep., priced at AU$235 found 13 hours ago
United
Thu, 4 Sep. - Wed, 10 Sep.
BOS
Boston
ORD
Chicago
AU$257 Return, found 13 hours ago
AU$257
Return
found 13 hours ago
Select United flight, departing Thu, 4 Sep. from Boston to Chicago, returning Wed, 10 Sep., priced at AU$257 found 13 hours ago
JetBlue Airways
Thu, 25 Dec. - Fri, 2 Jan.
BOS
Boston
ORD
Chicago
AU$305 Return, found 5 days ago
AU$305
Return
found 5 days ago
Select JetBlue Airways flight, departing Thu, 25 Dec. from Boston to Chicago, returning Fri, 2 Jan., priced at AU$305 found 5 days ago

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

September is typically the cheapest month to fly

From AU$74 - AU$174 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.