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

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Low fares from Albany to Chicago (O'Hare)

$

Albany (ALB)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$129
Seen: 9 hrs ago

Albany (ALB)to

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

One-way

Basic

From
$140
Seen: 22 hrs ago

Albany (ALB)to

Chicago (Midway) (MDW)
Depart: 10/24/2026

One-way

Basic

From
$140
Seen: 22 hrs ago

Albany (ALB)to

Chicago (Midway) (MDW)
Depart: 09/24/2026

One-way

Basic

From
$140
Seen: 20 hrs ago

Albany (ALB)to

Chicago (Midway) (MDW)
Depart: 09/23/2026

One-way

Basic

From
$140
Seen: 19 hrs ago

Albany (ALB)to

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

One-way

Basic

From
$140
Seen: 20 hrs ago

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Explore flights from Albany to Chicago (O'Hare)

Aug 2026
From$140*
Seen: 21 hrs ago
One Way/Basic
Sep 2026
From$129*
Seen: 9 hrs ago
One Way/Basic
Oct 2026
From$140*
Seen: 18 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $140
cmp-daily-histogram-bars-legend-max-price-aria-label $422
Displaying fares for August-2026
  • ALB–MDW, 08/05/2026: From $252
    05

    Wed

    AUG

  • ALB–MDW, 08/06/2026: From $249
    06

    Thu

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

    Fri

  • ALB–MDW, 08/08/2026: From $224
    08

    Sat

  • ALB–MDW, 08/09/2026: From $359
    09

    Sun

  • ALB–MDW, 08/10/2026: From $422
    10

    Mon

  • ALB–MDW, 08/11/2026: From $224
    11

    Tue

  • ALB–MDW, 08/12/2026: From $224
    12

    Wed

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    13

    Thu

  • ALB–MDW, 08/14/2026: From $249
    14

    Fri

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

    Sat

  • ALB–MDW, 08/16/2026: From $315
    16

    Sun

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    17

    Mon

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

    Tue

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

    Wed

  • ALB–MDW, 08/20/2026: From $227
    20

    Thu

  • ALB–MDW, 08/21/2026: From $227
    21

    Fri

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    22

    Sat

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

    Sun

  • ALB–MDW, 08/24/2026: From $227
    24

    Mon

  • ALB–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

  • ALB–MDW, 08/26/2026: From $140
    26

    Wed

  • ALB–MDW, 08/27/2026: From $140
    27

    Thu

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    28

    Fri

  • ALB–MDW, 08/29/2026: From $140
    29

    Sat

  • ALB–MDW, 08/30/2026: From $200
    30

    Sun

  • ALB–MDW, 08/31/2026: From $150
    31

    Mon

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    01

    Tue

    SEP

  • ALB–MDW, 09/02/2026: From $140
    02

    Wed

  • ALB–MDW, 09/03/2026: From $140
    03

    Thu

  • ALB–MDW, 09/04/2026: From $160
    04

    Fri

    • Range$140-$422

    *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:
    Albany International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    723 miles

    Route Information

    33† 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 33 weekly flights from Albany to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Albany 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 Albany 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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