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: 10/06/2026

One-way

Basic

From
$139
Seen: 11 hrs ago

Albany (ALB)to

Chicago (Midway) (MDW)
Depart: 12/02/2026

One-way

Basic

From
$139
Seen: 8 hrs ago

Albany (ALB)to

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

One-way

Basic

From
$139
Seen: 12 hrs ago

Albany (ALB)to

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

One-way

Basic

From
$139
Seen: 13 hrs ago

Albany (ALB)to

Chicago (Midway) (MDW)
Depart: 10/19/2026

One-way

Basic

From
$139
Seen: 14 hrs ago

Albany (ALB)to

Chicago (Midway) (MDW)
Depart: 09/16/2026

One-way

Basic

From
$139
Seen: 16 hrs ago

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Explore flights from Albany to Chicago (O'Hare)

Aug 2026
From$224*
Seen: 2 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$139*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $139
cmp-daily-histogram-bars-legend-max-price-aria-label $249
Displaying fares for August-2026
  • ALB–MDW, 08/25/2026: From $224
    25

    Tue

    AUG

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

    Wed

  • ALB–MDW, 08/27/2026: From $249
    27

    Thu

  • ALB–MDW, 08/28/2026: From $249
    28

    Fri

  • ALB–MDW, 08/29/2026: From $224
    29

    Sat

  • ALB–MDW, 08/30/2026: From $249
    30

    Sun

  • ALB–MDW, 08/31/2026: From $249
    31

    Mon

  • ALB–MDW, 09/01/2026: From $224
    01

    Tue

    SEP

  • ALB–MDW, 09/02/2026: From $224
    02

    Wed

  • ALB–MDW, 09/03/2026: From $249
    03

    Thu

  • ALB–MDW, 09/04/2026: From $249
    04

    Fri

  • ALB–MDW, 09/05/2026: From $169
    05

    Sat

  • ALB–MDW, 09/06/2026: From $169
    06

    Sun

  • ALB–MDW, 09/07/2026: From $227
    07

    Mon

  • ALB–MDW, 09/08/2026: From $224
    08

    Tue

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

    Wed

  • ALB–MDW, 09/10/2026: From $169
    10

    Thu

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

    Fri

  • ALB–MDW, 09/12/2026: From $169
    12

    Sat

  • ALB–MDW, 09/13/2026: From $237
    13

    Sun

  • ALB–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

  • ALB–MDW, 09/21/2026: From $190
    21

    Mon

  • ALB–MDW, 09/22/2026: From $139
    22

    Tue

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

    Wed

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

    Thu

    • Range$139-$249

    *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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