Southwest® flights from Rochester to Chicago-Midway from $139

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Low fares from Rochester to Chicago-Midway

$

Rochester (ROC)to

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

One-way

Basic

From
$139
Seen: 20 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$139
Seen: 14 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 10/28/2026

One-way

Basic

From
$139
Seen: 13 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 10/26/2026

One-way

Basic

From
$139
Seen: 13 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 10/27/2026

One-way

Basic

From
$139
Seen: 3 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$139
Seen: 7 hrs ago

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Explore flights from Rochester to Chicago-Midway

Oct 2026
From$139*
Seen: 13 hrs ago
One Way/Basic
Nov 2026
From$139*
Seen: 2 hrs ago
One Way/Basic
Dec 2026
From$139*
Seen: 15 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $399
Displaying fares for October-2026
  • ROC–MDW, 10/01/2026: From $390
    01

    Thu

    OCT

  • ROC–MDW, 10/02/2026: From $390
    02

    Fri

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    03

    Sat

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    04

    Sun

  • ROC–MDW, 10/05/2026: From $390
    05

    Mon

  • ROC–MDW, 10/06/2026: From $355
    06

    Tue

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    07

    Wed

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

    Thu

  • ROC–MDW, 10/09/2026: From $399
    09

    Fri

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

    Sat

  • ROC–MDW, 10/11/2026: From $390
    11

    Sun

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    12

    Mon

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    13

    Tue

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    14

    Wed

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    15

    Thu

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    16

    Fri

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    17

    Sat

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    18

    Sun

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    19

    Mon

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    20

    Tue

  • ROC–MDW, 10/21/2026: From $139
    21

    Wed

  • ROC–MDW, 10/22/2026: From $173
    22

    Thu

  • ROC–MDW, 10/23/2026: From $179
    23

    Fri

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    24

    Sat

  • ROC–MDW, 10/25/2026: From $242
    25

    Sun

  • ROC–MDW, 10/26/2026: From $139
    26

    Mon

  • ROC–MDW, 10/27/2026: From $139
    27

    Tue

  • ROC–MDW, 10/28/2026: From $139
    28

    Wed

  • ROC–MDW, 10/29/2026: From $139
    29

    Thu

  • ROC–MDW, 10/30/2026: From $173
    30

    Fri

  • ROC–MDW, 10/31/2026: From $139
    31

    Sat

    • Range$139-$399

    *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

    Route Information

    79† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 1‡ Nonstop flight on Sunday

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    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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