Southwest® flights from Rochester to Chicago (O'Hare)

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Low fares from Rochester to Chicago (O'Hare)

$

Rochester (ROC)to

Chicago (Midway) (MDW)
Depart: 10/01/2026

One-way

Basic

From
$139
Seen: 8 hrs ago

Rochester (ROC)to

Chicago (Midway) (MDW)
Depart: 11/26/2026

One-way

Basic

From
$139
Seen: 10 hrs ago

Rochester (ROC)to

Chicago (Midway) (MDW)
Depart: 09/17/2026

One-way

Basic

From
$139
Seen: 15 hrs ago

Rochester (ROC)to

Chicago (Midway) (MDW)
Depart: 09/14/2026

One-way

Basic

From
$139
Seen: 13 hrs ago

Rochester (ROC)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$139
Seen: 13 hrs ago

Rochester (ROC)to

Chicago (Midway) (MDW)
Depart: 10/20/2026

One-way

Basic

From
$139
Seen: 12 hrs ago

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Explore flights from Rochester to Chicago (O'Hare)

Aug 2026
From$335*
Seen: 8 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$139*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $370
Displaying fares for August-2026
  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

    AUG

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

    Wed

  • ROC–MDW, 08/27/2026: From $370
    27

    Thu

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

    Fri

  • ROC–MDW, 08/29/2026: From $335
    29

    Sat

  • ROC–MDW, 08/30/2026: From $370
    30

    Sun

  • ROC–MDW, 08/31/2026: From $370
    31

    Mon

  • ROC–MDW, 09/01/2026: From $335
    01

    Tue

    SEP

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

    Wed

  • ROC–MDW, 09/03/2026: From $370
    03

    Thu

  • ROC–MDW, 09/04/2026: From $370
    04

    Fri

  • ROC–MDW, 09/05/2026: From $255
    05

    Sat

  • ROC–MDW, 09/06/2026: From $255
    06

    Sun

  • ROC–MDW, 09/07/2026: From $250
    07

    Mon

  • ROC–MDW, 09/08/2026: From $250
    08

    Tue

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • ROC–MDW, 09/10/2026: From $250
    10

    Thu

  • ROC–MDW, 09/11/2026: From $250
    11

    Fri

  • ROC–MDW, 09/12/2026: From $250
    12

    Sat

  • ROC–MDW, 09/13/2026: From $250
    13

    Sun

  • ROC–MDW, 09/14/2026: From $139
    14

    Mon

  • ROC–MDW, 09/15/2026: From $139
    15

    Tue

  • ROC–MDW, 09/16/2026: From $139
    16

    Wed

  • ROC–MDW, 09/17/2026: From $139
    17

    Thu

  • ROC–MDW, 09/18/2026: From $153
    18

    Fri

  • ROC–MDW, 09/19/2026: From $139
    19

    Sat

  • ROC–MDW, 09/20/2026: From $169
    20

    Sun

  • ROC–MDW: cmp-view-offers-disclaimer. Find Offers
    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 $163
    24

    Thu

    • Range$139-$370

    *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:
    O'Hare International Airport
    Distance:
    528 miles

    Route Information

    13† Weekly flights

    † 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

    There are 13 weekly flights from Rochester to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Rochester to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Rochester to Chicago (O'Hare)—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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