Flights from Fort Myers, FL to Chicago, IL

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Best Deals on Flights From Fort Myers, FL (RSW) to Chicago, IL (ORD)

Oct 2026
from$185*
Last seen: 4 hours ago
One-way/Economy
Nov 2026
from$70*
Last seen: 23 hours ago
One-way/Economy
Dec 2026
from$70*
Last seen: 5 hours ago
One-way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label $70
Displaying fares for October-2026
  • RSW–ORD: cmp-view-offers-disclaimer. Find Offers
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  • RSW–ORD, Oct 29, 2026: from $185
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  • RSW–ORD, Oct 30, 2026: from $185
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    NOV

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  • RSW–ORD, Nov 20, 2026: from $103
    20

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  • RSW–ORD, Nov 21, 2026: from $70
    21

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    • Range$70-$185

    *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 Fort Myers, FL to Chicago, IL on Frontier

    $
    Flights Deals from Fort Myers, FL to Chicago, IL on Frontier
    From
    To
    Fort Myers, FL (RSW)Chicago, IL (ORD)One-way
    /
    Discount Den Basic Fare    		Departing Jan 27, 2027

    From

    $70

    Last seen: 23 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®.

    Fort Myers, FL Chicago, IL

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