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Cheap Flights from Chicago (ORD) to Boston (BOS) start at $55 for one-way and $107 for round trip. Earn your airline miles on top of our rewards!

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$55 Cheap Flights From Chicago To Boston (ORD To BOS) - Expedia

1 week from now

Cheap Flights from Chicago (ORD) to Boston (BOS) start at $55 for one-way and $107 for round trip. Earn your airline miles on top of our rewards!

expedia.com

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$55 Cheap Flights From Chicago (MDW) To Boston (BOS) - Expedia

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Cheap Flights from Chicago (MDW) to Boston (BOS) start at $55 for one-way and $114 for round trip. Earn your airline miles on top of our rewards!

expedia.com

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$59 Cheap Flights From Chicago (CHI) To Boston (BOS) - Expedia

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Cheap Flights from Chicago (CHI) to Boston (BOS) start at $59 for one-way and $118 for round trip. Earn your airline miles on top of our rewards!

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$109
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Cheap Flights From Chicago (ORD) To Boston (BOS) From S$109

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$86
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CA $86 Cheap Flights From Chicago (ORD) To Boston (BOS)

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CA $86 Cheap Flights From Chicago (CHI) To Boston (BOS)

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$114
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$114 Cheap Delta Flights Chicago (ORD) To Boston (BOS)

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expedia-aarp.com

$69
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$69 Cheap Delta Flights Chicago (ORD) To Boston (BOS)

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expedia.com

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£63 Cheap Flights From Chicago (CHI) To Boston (BOS)

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Reserve one-way or return flights from Chicago to Boston with no change fee on selected flights. Earn your airline miles on top of our rewards! Get 2025 flight deals for now!

expedia.co.uk