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: 11/05/2026

One-way

Basic

From
$139
Seen: 19 hrs ago

Rochester (ROC)to

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

One-way

Basic

From
$139
Seen: 16 hrs ago

Rochester (ROC)to

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

One-way

Basic

From
$139
Seen: 3 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 10/31/2026

One-way

Basic

From
$139
Seen: 7 hrs ago

Rochester (ROC)to

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

One-way

Basic

From
$139
Seen: 15 hrs ago

Rochester (ROC)to

Chicago-Midway (MDW)
Depart: 11/04/2026

One-way

Basic

From
$139
Seen: 16 hrs ago

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Explore flights from Rochester to Chicago-Midway

Sep 2026
From$139*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$139*
Seen: 7 hrs ago
One Way/Basic
Nov 2026
From$139*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $319
Displaying fares for September-2026
  • ROC–MDW, 09/10/2026: From $319
    10

    Thu

    SEP

  • ROC–MDW, 09/11/2026: From $319
    11

    Fri

  • ROC–MDW, 09/12/2026: From $302
    12

    Sat

  • ROC–MDW, 09/13/2026: From $319
    13

    Sun

  • ROC–MDW, 09/14/2026: From $319
    14

    Mon

  • ROC–MDW, 09/15/2026: From $302
    15

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

  • ROC–MDW, 09/21/2026: From $319
    21

    Mon

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

    Tue

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

    Wed

  • ROC–MDW, 09/24/2026: From $260
    24

    Thu

  • ROC–MDW, 09/25/2026: From $260
    25

    Fri

  • ROC–MDW, 09/26/2026: From $260
    26

    Sat

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

    Sun

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Mon

  • ROC–MDW, 09/29/2026: From $260
    29

    Tue

  • ROC–MDW, 09/30/2026: From $139
    30

    Wed

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Thu

    OCT

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

    Fri

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    03

    Sat

  • ROC–MDW, 10/04/2026: From $242
    04

    Sun

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    05

    Mon

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Tue

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Wed

  • ROC–MDW, 10/08/2026: From $275
    08

    Thu

  • ROC–MDW, 10/09/2026: From $292
    09

    Fri

    • Range$139-$319

    *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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