MDW - COS

$154 Find Cheap Flights from Chicago Midway Airport to Colorado Springs - Compare and Save

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Everything you should know

Cheapest round-trip
$317
Typical prices: $322-$443
Southwest
Sun 10/21Sun 10/28
MDW - COS • 1 stop
Cheapest non-stop
$335
Typical prices: $356-$454
Southwest
Mon 10/22Mon 10/29
MDW - COS • Non-stop
Nonstop flights
5 days a week
You can fly direct with Southwest. Average duration is 2h 35m
Direct flights
+1
Direct flights
+1
When to travel
April
Cheapest • 26% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Dallas Love Field (DAL)
Cheapest • Avg $453 (round-trip)
Denver Intl (DEN)
Shortest trip • 4h 31m (one-way)
Insights
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Booking Insights
Flight Deals

Cheap Flights from Midway to Colorado Springs (MDW-COS)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Colorado Springs

Thu, Oct 22 - Thu, Oct 29
Southwest Logo
5:15 am - 10:15 amMDW  Chicago Midway-COS Colorado Springs
6h 00m1 stop Dallas Love Field
Southwest Logo
2:05 pm - 5:25 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
$317Southwest
Wed, Oct 21 - Wed, Oct 28
Southwest Logo
6:05 am - 9:45 amMDW  Chicago Midway-COS Colorado Springs
4h 40m1 stop Denver Intl
Southwest Logo
12:40 pm - 4:00 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
$317Southwest
Tue, Oct 20 - Sat, Oct 24
Southwest Logo
2:50 pm - 7:55 pmMDW  Chicago Midway-COS Colorado Springs
6h 05m1 stop Dallas Love Field
Southwest Logo
7:55 am - 11:15 amCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
$317Southwest
Tue, Oct 20 - Sat, Oct 24
Southwest Logo
5:45 am - 11:05 amMDW  Chicago Midway-COS Colorado Springs
6h 20m1 stop Phoenix Sky Harbor Intl
Southwest Logo
7:55 am - 11:15 amCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
$317Southwest
Thu, Oct 29 - Thu, Nov 12
Southwest Logo
11:50 am - 1:25 pmMDW  Chicago Midway-COS Colorado Springs
2h 35mnonstop
Southwest Logo
7:45 pm - 5:45 amCOS  Colorado Springs-MDW Chicago Midway
9h 00m1 stop Phoenix Sky Harbor Intl
$317Southwest
Wed, Oct 21 - Wed, Oct 28
Southwest Logo
6:05 am - 9:45 amMDW  Chicago Midway-COS Colorado Springs
4h 40m1 stop Denver Intl
Southwest Logo
12:40 pm - 4:00 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
$317Southwest
Tue, Oct 20 - Sat, Oct 24
Southwest Logo
11:30 am - 7:55 pmMDW  Chicago Midway-COS Colorado Springs
9h 25m2 stops Birmingham Dallas Love Field
Southwest Logo
7:55 am - 11:15 amCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
$322Southwest
Fri, Oct 30 - Mon, Nov 2
Southwest Logo
11:50 am - 1:25 pmMDW  Chicago Midway-COS Colorado Springs
2h 35mnonstop
Southwest Logo
7:45 pm - 5:45 amCOS  Colorado Springs-MDW Chicago Midway
9h 00m1 stop Phoenix Sky Harbor Intl
$325Southwest
Tue, Jan 26 - Wed, Feb 3
Delta Logo
6:00 am - 12:58 pmMDW  Chicago Midway-COS Colorado Springs
7h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:10 pmCOS  Colorado Springs-MDW Chicago Midway
7h 30m1 stop Atlanta Hartsfield-Jackson
$327Delta
Mon, Jan 25 - Sat, Jan 30
Delta Logo
6:00 am - 12:58 pmMDW  Chicago Midway-COS Colorado Springs
7h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:10 pmCOS  Colorado Springs-MDW Chicago Midway
7h 30m1 stop Atlanta Hartsfield-Jackson
$327Delta
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Colorado Springs flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Colorado Springs?

Round-trip flights from Chicago Midway Airport to Colorado Springs typically range from $322 to $443. The lowest price found in the past 5 days was $317, on Southwest.

What's the cheapest day of the week to fly from Chicago Midway Airport to Colorado Springs?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago Midway Airport to Colorado Springs. It’s 28% cheaper than the average day, while Saturday is the most expensive, with prices 46% higher.

What’s the cheapest month to fly from Chicago Midway Airport to Colorado Springs?

•April is the cheapest month to fly from Chicago Midway Airport to Colorado Springs at $281 round-trip.
•December ($557) and March ($543) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 98% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Chicago Midway Airport to Colorado Springs flights

Low season

January

Cheapest flight

$154
Beat the crowds with an average 74% drop in travelers.
The most popular month to fly with an average 206% increase in travelers.
One-way flight from Chicago Midway Airport to Colorado Springs

When to book flights from Midway to Colorado Springs

Are your dates flexible? Find out the best times to travel from Midway to Colorado Springs based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Colorado Springs flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago Midway Airport to Colorado Springs?

    These are the earliest and latest flight times available from Chicago Midway Airport to Colorado Springs:

    • Earliest: departs at 10:00 am and lands at 12:35 pm
    • Latest: departs at 6:10 pm and lands at 8:45 pm.

    The flight takes about 2h 35m.

  • What cabin classes can I book on flights from Chicago Midway Airport to Colorado Springs?

    Only Economy Class is available on flights from Chicago Midway Airport to Colorado Springs.

  • How long is a flight from Chicago Midway Airport to Colorado Springs?

    A nonstop flight from Chicago Midway Airport to Colorado Springs takes 2h 35m, covering 915 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Colorado Springs?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to Colorado Springs flight?

    Round-trip flights from Chicago Midway Airport to Colorado Springs range from $322 to $443, with an average of $380 over the past 12 months. Anything below $322 counts as a good deal.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to Colorado Springs?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $391 round-trip, compared to $453 via a layover through Dallas Love Field (DAL).

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to Colorado Springs?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to Colorado Springs?

    The Canadair (Bombardier) Regional Jet 700 family is used most often on this route, operated mainly by American Airlines. Other aircraft seen on the route include Embraer 175 (Enhanced Winglets) variants.

  • Have flight prices from Chicago Midway Airport to Colorado Springs changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $317 to $2,080. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on Chicago Midway Airport to Colorado Springs flights?

    JetBlue is the only airline on the Chicago Midway Airport to Colorado Springs route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Chicago Midway Airport to Colorado Springs looking right now?

    One-way fares from Chicago Midway Airport to Colorado Springs are currently lower than usual. Average one-way flight prices are about $161, which is 29% below the typical average for this route.

  • What car rental options are available at Colorado Springs Airport (COS)?

    Colorado Springs Airport (COS) hosts 5 major car rental companies, with daily rates starting from around $31 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Budget
    • Alamo
    • Avis

  • Which airports can I use when flying from Chicago Midway Airport to Colorado Springs?

    Flights from Chicago Midway Airport to Colorado Springs usually depart from Chicago Midway (MDW) and arrive at Colorado Springs (COS).

  • Which airports do connecting flights from Chicago Midway Airport to Colorado Springs pass through?

    One-stop flights from Chicago Midway Airport to Colorado Springs most commonly connect through:

    • Denver Intl (DEN) - 67% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 17% of one-stop connections
    • Dallas Love Field (DAL) - 17% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Colorado Springs?

    Yes. Flexible dates can save you up to 51% on flights from Chicago Midway Airport to Colorado Springs. Wednesday is the cheapest departure day at $274 round-trip on average, while Saturday is the most expensive at $557, a difference of $283.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago Midway Airport to Colorado Springs?

    Only Southwest operates flights between Chicago Midway Airport and Colorado Springs.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Colorado Springs?

    Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 4h 31m, compared with 5h 37m via Dallas Love Field (DAL) and 6h 53m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Chicago Midway Airport and Colorado Springs?

    Colorado Springs is 1 hour behind Chicago Midway Airport (Mountain Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Colorado Springs?

    Some of the most popular sights in Colorado Springs are Garden of the Gods, United States Air Force Academy and Peterson Air and Space Museum. These are among the most viewed places in Colorado Springs on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to Colorado Springs flights?

    Among airlines operating Chicago Midway Airport to Colorado Springs flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Colorado Springs flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy Class class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to Colorado Springs flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Saturday. On this route, Wednesday flights average $274, about $283 less than Saturday fares (51% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to Colorado Springs trip for April. Fares historically average $281 round-trip in that month - typically $276 less than the most expensive month, which is December (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Colorado Springs Airport.

    • Radisson Hotel Colorado Springs Airport, CO
    • Tru by Hilton Colorado Springs Airport
    • Hyatt House Colorado Springs Airport

Prefer to fly direct from Chicago Midway Airport to Colorado Springs?

 
Find which airlines fly direct from Chicago Midway Airport to Colorado Springs Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Colorado Springs

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Colorado Springs to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

More options for your flight from Midway to Colorado Springs

Complete your trip to Colorado Springs with a hotel stay or car rental

Car rentals in Colorado Springs
Hotels in Colorado Springs
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