Flights from Orlando, FL to Chicago, IL

Promo Code

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

Aug 2026
from$95*
Last seen: 23 hours ago
One-way/Economy
Sep 2026
from$82*
Last seen: 12 hours ago
One-way/Economy
Oct 2026
from$101*
Last seen: 20 hours ago
One-way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label $95
cmp-daily-histogram-bars-legend-max-price-aria-label $210
Displaying fares for August-2026
  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Sat

    AUG

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Sun

  • MCO–MDW, Aug 3, 2026: from $179
    03

    Mon

  • MCO–MDW, Aug 4, 2026: from $179
    04

    Tue

  • MCO–MDW, Aug 5, 2026: from $179
    05

    Wed

  • MCO–MDW, Aug 6, 2026: from $179
    06

    Thu

  • MCO–MDW, Aug 7, 2026: from $160
    07

    Fri

  • MCO–MDW, Aug 8, 2026: from $158
    08

    Sat

  • MCO–MDW, Aug 9, 2026: from $179
    09

    Sun

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

    Mon

  • MCO–MDW, Aug 11, 2026: from $158
    11

    Tue

  • MCO–MDW, Aug 12, 2026: from $158
    12

    Wed

  • MCO–MDW, Aug 13, 2026: from $169
    13

    Thu

  • MCO–MDW, Aug 14, 2026: from $167
    14

    Fri

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

    Sat

  • MCO–MDW, Aug 16, 2026: from $210
    16

    Sun

  • MCO–MDW, Aug 17, 2026: from $161
    17

    Mon

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Tue

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Wed

  • MCO–MDW, Aug 20, 2026: from $161
    20

    Thu

  • MCO–MDW, Aug 21, 2026: from $161
    21

    Fri

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

    Sat

  • MCO–MDW, Aug 23, 2026: from $118
    23

    Sun

  • MCO–MDW, Aug 24, 2026: from $95
    24

    Mon

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

  • MCO–MDW, Aug 27, 2026: from $95
    27

    Thu

  • MCO–MDW, Aug 28, 2026: from $105
    28

    Fri

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

    Sat

  • MCO–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

  • MCO–MDW, Aug 31, 2026: from $95
    31

    Mon

    • Range$95-$210

    *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 Nov 11, 2026

    From

    $52

    Last seen: 13 hours ago

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

    From

    $95

    Last seen: 15 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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