Flights from Boston, MA to Chicago, IL

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Best Deals on Flights From Boston, MA (BOS) to Chicago, IL (ORD)

Nov 2026
from$150*
Last seen: 13 hours ago
One-way/Economy
Dec 2026
from$133*
Last seen: 5 hours ago
One-way/Economy
Jan 2027
from$117*
Last seen: 15 hours ago
One-way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label $133
Displaying fares for November-2026
  • BOS–ORD: cmp-view-offers-disclaimer. Find Offers
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    NOV

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    11

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    12

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    13

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    18

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    20

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    21

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    22

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    23

    Mon

  • BOS–ORD, Nov 24, 2026: from $150
    24

    Tue

  • BOS–ORD, Nov 25, 2026: from $225
    25

    Wed

  • BOS–ORD, Nov 26, 2026: from $190
    26

    Thu

  • BOS–ORD: cmp-view-offers-disclaimer. Find Offers
    27

    Fri

  • BOS–ORD, Nov 28, 2026: from $580
    28

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  • BOS–ORD, Nov 29, 2026: from $423
    29

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  • BOS–ORD: cmp-view-offers-disclaimer. Find Offers
    30

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    01

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    DEC

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    02

    Wed

  • BOS–ORD, Dec 3, 2026: from $133
    03

    Thu

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    04

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    • Range$133-$580

    *Prices found by others in the previous 48 hours for round-trip flights. Prices shown may also require membership in our travel club, Discount Den.

    Flights Deals from Boston, MA to Chicago, IL on Frontier

    $
    Flights Deals from Boston, MA to Chicago, IL on Frontier
    From
    To
    Boston, MA (BOS)Chicago, IL (ORD)One-way
    /
    Discount Den Basic Fare    		Departing Mar 7, 2027

    From

    $203

    Last seen: 12 hours ago

    *Prices found by others in the previous 48 hours for one-way flights. Prices shown may also require membership in our travel club, Discount Den®.

    Boston, MA Chicago, IL

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