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

Promo Code

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

$

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 09/30/2026

One-way

Basic

From
$139
Seen: 12 hrs ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 10/29/2026

One-way

Basic

From
$139
Seen: 12 hrs ago

Colorado Springs (COS)to

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

One-way

Basic

From
$139
Seen: 15 hrs ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 10/22/2026

One-way

Basic

From
$139
Seen: 19 hrs ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 10/14/2026

One-way

Basic

From
$139
Seen: 36 minutes ago

Colorado Springs (COS)to

Chicago (Midway) (MDW)
Depart: 10/03/2026

One-way

Basic

From
$139
Seen: 18 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

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

Aug 2026
From$230*
Seen: 3 hrs ago
One Way/Basic
Sep 2026
From$139*
Seen: 12 hrs ago
One Way/Basic
Oct 2026
From$139*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $411
Displaying fares for August-2026
  • COS–MDW, 08/25/2026: From $240
    25

    Tue

    AUG

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

    Wed

  • COS–MDW, 08/27/2026: From $256
    27

    Thu

  • COS–MDW, 08/28/2026: From $256
    28

    Fri

  • COS–MDW, 08/29/2026: From $230
    29

    Sat

  • COS–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

  • COS–MDW, 08/31/2026: From $256
    31

    Mon

  • COS–MDW, 09/01/2026: From $230
    01

    Tue

    SEP

  • COS–MDW, 09/02/2026: From $230
    02

    Wed

  • COS–MDW, 09/03/2026: From $271
    03

    Thu

  • COS–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

  • COS–MDW, 09/05/2026: From $186
    05

    Sat

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

    Sun

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

    Mon

  • COS–MDW, 09/08/2026: From $309
    08

    Tue

  • COS–MDW, 09/09/2026: From $186
    09

    Wed

  • COS–MDW, 09/10/2026: From $176
    10

    Thu

  • COS–MDW, 09/11/2026: From $176
    11

    Fri

  • COS–MDW, 09/12/2026: From $176
    12

    Sat

  • COS–MDW, 09/13/2026: From $243
    13

    Sun

  • COS–MDW, 09/14/2026: From $149
    14

    Mon

  • COS–MDW, 09/15/2026: From $149
    15

    Tue

  • COS–MDW, 09/16/2026: From $177
    16

    Wed

  • COS–MDW, 09/17/2026: From $149
    17

    Thu

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

    Fri

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

    Sat

  • COS–MDW, 09/20/2026: From $411
    20

    Sun

  • COS–MDW, 09/21/2026: From $149
    21

    Mon

  • COS–MDW, 09/22/2026: From $149
    22

    Tue

  • COS–MDW, 09/23/2026: From $149
    23

    Wed

  • COS–MDW, 09/24/2026: From $149
    24

    Thu

    • Range$149-$411

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Colorado Springs