Southwest® flights from Colorado Springs to Chicago (O'Hare) from $145

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Low fares from Colorado Springs to Chicago (O'Hare)

$

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 06/05/2026

One-way

Basic

From
$135
Seen: 22 hrs ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 04/15/2026

One-way

Basic

From
$145
Seen: 22 hrs ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 04/18/2026

One-way

Basic

From
$145
Seen: 2 hrs ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 04/07/2026

One-way

Basic

From
$145
Seen: 1 hour ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 06/02/2026

One-way

Basic

From
$145
Seen: 1 hour ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 04/09/2026

One-way

Basic

From
$145
Seen: 1 hour ago

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Explore flights from Colorado Springs to Chicago (O'Hare)

Mar 2026
From$205*
Seen: 1 hour ago
One Way/Basic
Apr 2026
From$145*
Seen: 17 hrs ago
One Way/Basic
May 2026
From$145*
Seen: 3 hrs ago
One Way/Basic
$145
$325
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    • Range$145-$325

    *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:
    City of Colorado Springs Municipal Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    911 miles

    Route Information

    84† 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 84 weekly flights from Colorado Springs to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Colorado Springs 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 Colorado Springs 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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