Southwest® flights from Rochester to Chicago-Midway from $142

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Low fares from Rochester to Chicago-Midway

$

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$142
Seen: 22 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 11/14/2026

One-way

Basic

From
$142
Seen: 20 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$142
Seen: 18 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 01/07/2027

One-way

Basic

From
$142
Seen: 9 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 12/11/2026

One-way

Basic

From
$142
Seen: 2 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 01/27/2027

One-way

Basic

From
$142
Seen: 40 minutes ago

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Explore flights from Rochester to Chicago-Midway

Oct 2026
From$355*
Seen: 8 hrs ago
One Way/Basic
Nov 2026
From$142*
Seen: 20 hrs ago
One Way/Basic
Dec 2026
From$142*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $142
cmp-daily-histogram-bars-legend-max-price-aria-label $400
Displaying fares for October-2026
  • ROC–MDW, 10/21/2026: From $355
    21

    Wed

    OCT

  • ROC–MDW, 10/22/2026: From $400
    22

    Thu

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Fri

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    24

    Sat

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    25

    Sun

  • ROC–MDW, 10/26/2026: From $400
    26

    Mon

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Tue

  • ROC–MDW, 10/28/2026: From $355
    28

    Wed

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

    Thu

  • ROC–MDW, 10/30/2026: From $400
    30

    Fri

  • ROC–MDW, 10/31/2026: From $355
    31

    Sat

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    01

    Sun

    NOV

  • ROC–MDW, 11/02/2026: From $400
    02

    Mon

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    03

    Tue

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    04

    Wed

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    05

    Thu

  • ROC–MDW, 11/06/2026: From $280
    06

    Fri

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    07

    Sat

  • ROC–MDW, 11/08/2026: From $280
    08

    Sun

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    09

    Mon

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

    Tue

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

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    12

    Thu

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    13

    Fri

  • ROC–MDW, 11/14/2026: From $142
    14

    Sat

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

    Sun

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Mon

  • ROC–MDW, 11/17/2026: From $142
    17

    Tue

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

    Wed

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    19

    Thu

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    20

    Fri

    • Range$142-$400

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Greater Rochester International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 51 minutes
    Distance:
    523 miles

    Questions we hear the most

    The average flight time from Rochester to Chicago (Midway) is 1 hour 51 minutes.
    There are 79 weekly flights from Rochester to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Rochester to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Rochester to Chicago (Midway) once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Rochester to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Rochester to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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