Flights from Chicago, IL to Orlando, FL

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Best Deals on Flights From Chicago, IL (MDW) to Orlando, FL (MCO)

Try alternate month or interact with individual days below in order to find offers.
Aug 2026
No results for this month.
Sep 2026
from$101*
Last seen: 7 hours ago
One-way/Economy
Oct 2026
from$95*
Last seen: 2 hours ago
One-way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label $101
cmp-daily-histogram-bars-legend-max-price-aria-label $184
Displaying fares for August-2026
  • MDW–MCO: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

    AUG

  • MDW–MCO: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • MDW–MCO: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • MDW–MCO, Sep 2, 2026: from $159
    02

    Wed

  • MDW–MCO, Sep 3, 2026: from $159
    03

    Thu

  • MDW–MCO, Sep 4, 2026: from $184
    04

    Fri

  • MDW–MCO, Sep 5, 2026: from $119
    05

    Sat

  • MDW–MCO, Sep 6, 2026: from $174
    06

    Sun

  • MDW–MCO, Sep 7, 2026: from $179
    07

    Mon

  • MDW–MCO, Sep 8, 2026: from $149
    08

    Tue

  • MDW–MCO, Sep 9, 2026: from $108
    09

    Wed

  • MDW–MCO: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

  • MDW–MCO, Sep 11, 2026: from $108
    11

    Fri

  • MDW–MCO, Sep 12, 2026: from $112
    12

    Sat

  • MDW–MCO, Sep 13, 2026: from $184
    13

    Sun

  • MDW–MCO: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • MDW–MCO, Sep 15, 2026: from $129
    15

    Tue

  • MDW–MCO, Sep 16, 2026: from $129
    16

    Wed

  • MDW–MCO, Sep 17, 2026: from $129
    17

    Thu

  • MDW–MCO, Sep 18, 2026: from $129
    18

    Fri

  • MDW–MCO, Sep 19, 2026: from $129
    19

    Sat

  • MDW–MCO, Sep 20, 2026: from $184
    20

    Sun

  • MDW–MCO, Sep 21, 2026: from $128
    21

    Mon

  • MDW–MCO, Sep 22, 2026: from $128
    22

    Tue

  • MDW–MCO, Sep 23, 2026: from $128
    23

    Wed

  • MDW–MCO, Sep 24, 2026: from $128
    24

    Thu

  • MDW–MCO, Sep 25, 2026: from $128
    25

    Fri

  • MDW–MCO, Sep 26, 2026: from $101
    26

    Sat

  • MDW–MCO, Sep 27, 2026: from $159
    27

    Sun

  • MDW–MCO: cmp-view-offers-disclaimer. Find Offers
    28

    Mon

  • MDW–MCO: cmp-view-offers-disclaimer. Find Offers
    29

    Tue

    • Range$101-$184

    *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 Chicago, IL to Orlando, FL on Frontier

    $
    Flights Deals from Chicago, IL to Orlando, FL on Frontier
    From
    To
    Chicago, IL (ORD)Orlando, FL (MCO)One-way
    /
    Discount Den Basic Fare    		Departing Dec 2, 2026

    From

    $118

    Last seen: 16 hours ago

    Chicago, IL (MDW)Orlando, FL (MCO)One-way
    /
    Discount Den Basic Fare    		Departing Dec 5, 2026

    From

    $128

    Last seen: 20 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®.

    Chicago, IL Orlando, FL

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