Flights from Orlando, FL to Chicago, IL

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

Sep 2026
from$182*
Last seen: 37 mins ago
One-way/Economy
Oct 2026
from$77*
Last seen: 2 hours ago
One-way/Economy
Nov 2026
from$69*
Last seen: 5 hours ago
One-way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label $77
cmp-daily-histogram-bars-legend-max-price-aria-label $214
Displaying fares for September-2026
  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

    SEP

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

  • MCO–MDW, Sep 18, 2026: from $214
    18

    Fri

  • MCO–MDW, Sep 19, 2026: from $214
    19

    Sat

  • MCO–MDW, Sep 20, 2026: from $214
    20

    Sun

  • MCO–MDW, Sep 21, 2026: from $214
    21

    Mon

  • MCO–MDW, Sep 22, 2026: from $182
    22

    Tue

  • MCO–MDW, Sep 23, 2026: from $182
    23

    Wed

  • MCO–MDW, Sep 24, 2026: from $196
    24

    Thu

  • MCO–MDW, Sep 25, 2026: from $214
    25

    Fri

  • MCO–MDW, Sep 26, 2026: from $200
    26

    Sat

  • MCO–MDW, Sep 27, 2026: from $214
    27

    Sun

  • MCO–MDW, Sep 28, 2026: from $196
    28

    Mon

  • MCO–MDW, Sep 29, 2026: from $206
    29

    Tue

  • MCO–MDW, Sep 30, 2026: from $206
    30

    Wed

  • MCO–MDW, Oct 1, 2026: from $209
    01

    Thu

    OCT

  • MCO–MDW, Oct 2, 2026: from $209
    02

    Fri

  • MCO–MDW, Oct 3, 2026: from $206
    03

    Sat

  • MCO–MDW, Oct 4, 2026: from $209
    04

    Sun

  • MCO–MDW, Oct 5, 2026: from $106
    05

    Mon

  • MCO–MDW, Oct 6, 2026: from $86
    06

    Tue

  • MCO–MDW, Oct 7, 2026: from $77
    07

    Wed

  • MCO–MDW, Oct 8, 2026: from $111
    08

    Thu

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Fri

  • MCO–MDW, Oct 10, 2026: from $88
    10

    Sat

  • MCO–MDW, Oct 11, 2026: from $128
    11

    Sun

  • MCO–MDW, Oct 12, 2026: from $162
    12

    Mon

  • MCO–MDW, Oct 13, 2026: from $111
    13

    Tue

  • MCO–MDW, Oct 14, 2026: from $77
    14

    Wed

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Thu

    • Range$77-$214

    *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 Orlando, FL to Chicago, IL on Frontier

    $
    Flights Deals from Orlando, FL to Chicago, IL on Frontier
    From
    To
    Orlando, FL (MCO)Chicago, IL (ORD)One-way
    /
    Discount Den Basic Fare    		Departing Dec 16, 2026

    From

    $65

    Last seen: 10 hours ago

    Orlando, FL (MCO)Chicago, IL (MDW)One-way
    /
    Discount Den Basic Fare    		Departing Dec 22, 2026

    From

    $89

    Last seen: 7 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®.

    Orlando, FL Chicago, IL

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