Southwest® flights from Rochester to Chicago-Midway from $155

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Low fares from Rochester to Chicago-Midway

$

Rochester (ROC)to

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

One-way

Basic

From
$155
Seen: 18 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 02/09/2027

One-way

Basic

From
$155
Seen: 15 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$175
Seen: 13 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 12/07/2026

One-way

Basic

From
$175
Seen: 9 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$175
Seen: 5 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$175
Seen: 9 hrs ago

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Explore flights from Rochester to Chicago-Midway

Nov 2026
From$285*
Seen: 2 hrs ago
One Way/Basic
Dec 2026
From$175*
Seen: 9 hrs ago
One Way/Basic
Jan 2027
From$155*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $175
cmp-daily-histogram-bars-legend-max-price-aria-label $353
Displaying fares for November-2026
  • ROC–MDW, 11/13/2026: From $353
    13

    Fri

    NOV

  • ROC–MDW, 11/14/2026: From $353
    14

    Sat

  • ROC–MDW, 11/15/2026: From $348
    15

    Sun

  • ROC–MDW, 11/16/2026: From $353
    16

    Mon

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

    Tue

  • ROC–MDW, 11/18/2026: From $348
    18

    Wed

  • ROC–MDW, 11/19/2026: From $353
    19

    Thu

  • ROC–MDW, 11/20/2026: From $348
    20

    Fri

  • ROC–MDW, 11/21/2026: From $353
    21

    Sat

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

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

    Mon

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Tue

  • ROC–MDW, 11/25/2026: From $285
    25

    Wed

  • ROC–MDW, 11/26/2026: From $285
    26

    Thu

  • ROC–MDW, 11/27/2026: From $300
    27

    Fri

  • ROC–MDW, 11/28/2026: From $328
    28

    Sat

  • ROC–MDW, 11/29/2026: From $285
    29

    Sun

  • ROC–MDW, 11/30/2026: From $285
    30

    Mon

  • ROC–MDW, 12/01/2026: From $273
    01

    Tue

    DEC

  • ROC–MDW, 12/02/2026: From $290
    02

    Wed

  • ROC–MDW, 12/03/2026: From $175
    03

    Thu

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

  • ROC–MDW, 12/06/2026: From $262
    06

    Sun

  • ROC–MDW, 12/07/2026: From $175
    07

    Mon

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • ROC–MDW, 12/09/2026: From $175
    09

    Wed

  • ROC–MDW, 12/10/2026: From $175
    10

    Thu

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

    Fri

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

    • Range$175-$353

    *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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