Southwest® flights from Chicago-Midway to Denver from $148

Promo Code

Low fares from Chicago-Midway to Denver

$

Chicago-Midway (MDW)to

Denver (DEN)
Depart: 10/27/2026

One-way

Basic

From
$148
Seen: 15 hrs ago

Chicago-Midway (MDW)to

Denver (DEN)
Depart: 10/28/2026

One-way

Basic

From
$148
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Denver (DEN)
Depart: 10/14/2026

One-way

Basic

From
$148
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Denver (DEN)
Depart: 10/20/2026

One-way

Basic

From
$148
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Denver (DEN)
Depart: 11/17/2026

One-way

Basic

From
$148
Seen: 12 hrs ago

Chicago-Midway (MDW)to

Denver (DEN)
Depart: 12/22/2026

One-way

Basic

From
$148
Seen: 12 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 Chicago-Midway to Denver

Sep 2026
From$229*
Seen: 12 hrs ago
One Way/Basic
Oct 2026
From$148*
Seen: 13 hrs ago
One Way/Basic
Nov 2026
From$148*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $148
cmp-daily-histogram-bars-legend-max-price-aria-label $307
Displaying fares for September-2026
  • MDW–DEN, 09/14/2026: From $307
    14

    Mon

    SEP

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

    Tue

  • MDW–DEN, 09/16/2026: From $259
    16

    Wed

  • MDW–DEN, 09/17/2026: From $307
    17

    Thu

  • MDW–DEN, 09/18/2026: From $307
    18

    Fri

  • MDW–DEN, 09/19/2026: From $259
    19

    Sat

  • MDW–DEN, 09/20/2026: From $307
    20

    Sun

  • MDW–DEN, 09/21/2026: From $307
    21

    Mon

  • MDW–DEN, 09/22/2026: From $259
    22

    Tue

  • MDW–DEN, 09/23/2026: From $259
    23

    Wed

  • MDW–DEN, 09/24/2026: From $307
    24

    Thu

  • MDW–DEN, 09/25/2026: From $307
    25

    Fri

  • MDW–DEN, 09/26/2026: From $259
    26

    Sat

  • MDW–DEN, 09/27/2026: From $229
    27

    Sun

  • MDW–DEN, 09/28/2026: From $229
    28

    Mon

  • MDW–DEN, 09/29/2026: From $229
    29

    Tue

  • MDW–DEN, 09/30/2026: From $229
    30

    Wed

  • MDW–DEN, 10/01/2026: From $229
    01

    Thu

    OCT

  • MDW–DEN, 10/02/2026: From $229
    02

    Fri

  • MDW–DEN, 10/03/2026: From $229
    03

    Sat

  • MDW–DEN, 10/04/2026: From $188
    04

    Sun

  • MDW–DEN, 10/05/2026: From $188
    05

    Mon

  • MDW–DEN, 10/06/2026: From $188
    06

    Tue

  • MDW–DEN, 10/07/2026: From $188
    07

    Wed

  • MDW–DEN, 10/08/2026: From $188
    08

    Thu

  • MDW–DEN, 10/09/2026: From $188
    09

    Fri

  • MDW–DEN, 10/10/2026: From $188
    10

    Sat

  • MDW–DEN, 10/11/2026: From $188
    11

    Sun

  • MDW–DEN, 10/12/2026: From $208
    12

    Mon

  • MDW–DEN, 10/13/2026: From $148
    13

    Tue

    • Range$148-$307

    *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:
    Chicago Midway International Airport
    Arriving at:
    Denver International Airport
    Average flight time:
    2 hours 38 minutes
    Distance:
    895 miles

    Route Information

    156† Weekly flights
    • 6‡ Nonstop flights per day Monday through Friday
    • 5‡ Nonstop flights on Saturday
    • 7‡ Nonstop flights on Sunday

    † 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

    The average flight time from Chicago (Midway) to Denver is 2 hours 38 minutes.
    There are 156 weekly flights from Chicago (Midway) to Denver on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Denver 6 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Denver 5 times per day on Saturdays and 7 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Denver with Southwest, check out our Low Fare Calendar.
    You can rent a car at Denver International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Denver—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 Chicago-Midway