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Cheap flights from Colorado Springs to Chicago from $122

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Colorado Springs to Chicago departing on 4/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Colorado Springs to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:30 pm - 8:20 pm
COS
-
MDW
4h 50m
1 stop
Southwest Logo
10:00 am - 4:15 pm
MDW
-
COS
7h 15m
1 stop
$267Southwest
Wed, May 13 - Sat, May 16
Multiple Airlines Logo
10:39 am - 10:14 pm
COS
-
MDW
34h 35m
2 stops
Multiple Airlines Logo
6:20 am - 5:56 pm
MDW
-
COS
12h 36m
1 stop
$272Multiple Airlines
Mon, Apr 20 - Sun, Apr 26
Southwest Logo
4:05 pm - 11:55 pm
COS
-
MDW
6h 50m
1 stop
Southwest Logo
5:25 am - 11:35 am
MDW
-
COS
7h 10m
1 stop
$291Southwest
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
10:39 am - 10:14 pm
COS
-
MDW
34h 35m
2 stops
Multiple Airlines Logo
6:20 am - 5:56 pm
MDW
-
COS
12h 36m
1 stop
$294Multiple Airlines
Mon, Apr 20 - Sun, Apr 26
Southwest Logo
2:15 pm - 4:35 am
COS
-
MDW
13h 20m
1 stop
Southwest Logo
6:25 pm - 11:50 pm
MDW
-
COS
6h 25m
1 stop
$296Southwest
Thu, Apr 30 - Mon, May 4
Southwest Logo
7:20 pm - 5:00 am
COS
-
MDW
8h 40m
1 stop
Southwest Logo
6:00 am - 9:20 am
MDW
-
COS
4h 20m
1 stop
$298Southwest
Thu, Apr 23 - Thu, Apr 30
Southwest Logo
12:40 pm - 9:45 pm
COS
-
MDW
8h 05m
2 stops
Southwest Logo
7:50 am - 1:40 pm
MDW
-
COS
6h 50m
2 stops
$301Southwest
Wed, May 13 - Sat, May 16
Southwest Logo
2:15 pm - 4:35 am
COS
-
MDW
13h 20m
1 stop
Southwest Logo
5:30 am - 1:35 pm
MDW
-
COS
9h 05m
2 stops
$302Southwest
Thu, Apr 30 - Mon, May 4
Southwest Logo
5:20 pm - 11:40 pm
COS
-
MDW
5h 20m
1 stop
Southwest Logo
4:35 pm - 12:05 am
MDW
-
COS
8h 30m
2 stops
$304Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
4:05 pm - 11:55 pm
COS
-
MDW
6h 50m
1 stop
Southwest Logo
5:25 am - 11:35 am
MDW
-
COS
7h 10m
1 stop
$306Southwest
Thu, Apr 16 - Mon, Apr 20

Southwest flights from Colorado Springs to Chicago Midway Airport

Our best Southwest deals on Colorado Springs to Chicago Midway Airport flight tickets
Southwest
May 13
COS2:30 pmColorado Springs
4h 50m
1 stop
MDW8:20 pmChicago Midway
May 16
MDW10:00 amChicago Midway
7h 15m
1 stop
COS4:15 pmColorado Springs
$267
Southwest
May 7
COS4:05 pmColorado Springs
6h 50m
1 stop
MDW11:55 pmChicago Midway
May 11
MDW5:25 amChicago Midway
7h 10m
1 stop
COS11:35 amColorado Springs
$291
Southwest
Apr 30
COS2:15 pmColorado Springs
13h 20m
1 stop
MDW4:35 amChicago Midway
May 4
MDW6:25 pmChicago Midway
6h 25m
1 stop
COS11:50 pmColorado Springs
$296

Delta flights from Colorado Springs to Chicago Midway Airport

Our best Delta deals on Colorado Springs to Chicago Midway Airport flight tickets
Delta
May 20
COS1:55 pmColorado Springs
6h 14m
1 stop
MDW9:09 pmChicago Midway
May 29
MDW6:23 amChicago Midway
7h 25m
1 stop
COS12:48 pmColorado Springs
$324
Delta
May 20
COS1:55 pmColorado Springs
6h 14m
1 stop
MDW9:09 pmChicago Midway
May 29
MDW1:22 pmChicago Midway
10h 00m
2 stops
COS10:22 pmColorado Springs
$329
Delta
May 20
COS1:55 pmColorado Springs
6h 14m
1 stop
MDW9:09 pmChicago Midway
May 29
MDW1:22 pmChicago Midway
10h 00m
2 stops
COS10:22 pmColorado Springs
$346

momondo Fare Finder

 
Customize your flight search to find flights from Colorado Springs to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 28, 2026.
Use the filters below to find and compare flights from Colorado Springs to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 5/13

2:30 pm-8:20 pm

1 stop4h 50m

Chicago Midway

Sat 5/16

10:00 am-4:15 pm

1 stop7h 15m

$267

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Mon 4/20

10:39 am-10:14 pm

2 stops34h 35m

Chicago Midway

Sun 4/26

6:20 am-5:56 pm

1 stop12h 36m

$272

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 5/7

4:05 pm-11:55 pm

1 stop6h 50m

Chicago Midway

Mon 5/11

5:25 am-11:35 am

1 stop7h 10m

$291

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Mon 4/20

10:39 am-10:14 pm

2 stops34h 35m

Chicago Midway

Sun 4/26

6:20 am-5:56 pm

1 stop12h 36m

$294

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/30

2:15 pm-4:35 am

1 stop13h 20m

Chicago Midway

Mon 5/4

6:25 pm-11:50 pm

1 stop6h 25m

$296

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/23

7:20 pm-5:00 am

1 stop8h 40m

Chicago Midway

Thu 4/30

6:00 am-9:20 am

1 stop4h 20m

$298

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 5/13

12:40 pm-9:45 pm

2 stops8h 05m

Chicago Midway

Sat 5/16

7:50 am-1:40 pm

2 stops6h 50m

$301

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/30

2:15 pm-4:35 am

1 stop13h 20m

Chicago Midway

Mon 5/4

5:30 am-1:35 pm

2 stops9h 05m

$302

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Mon 4/20

5:20 pm-11:40 pm

1 stop5h 20m

Chicago Midway

Mon 4/27

4:35 pm-12:05 am

2 stops8h 30m

$304

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/16

4:05 pm-11:55 pm

1 stop6h 50m

Chicago Midway

Mon 4/20

5:25 am-11:35 am

1 stop7h 10m

$306

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Colorado Springs to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Colorado Springs and Chicago Midway Airport?

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Colorado Springs. The lowest ticket price found for a Wednesday departure recently was $352. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Colorado Springs because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $461.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Colorado Springs at noon is the least expensive time of day to depart. momondo users have found prices as low as $383 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $455. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Colorado Springs to Chicago Midway flight route?

Fly from Colorado Springs to Chicago Midway for the best Colorado Springs - Chicago Midway flight prices

What cabin class options are available on Colorado Springs to Chicago Midway flights?

There is only 1 cabin class available to choose from on Colorado Springs to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Colorado Springs to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Colorado Springs to Chicago Midway Airport.

When to book flights from Colorado Springs to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Colorado Springs to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Colorado Springs to Chicago Midway Airport (COS to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Colorado Springs to Chicago Midway Airport

Best Price Found

$478

Fastest flight time

2h 20m

Direct flights

Every day
The best flight deal from Colorado Springs to Chicago Midway Airport found on momondo in the last 72 hours is $478
The fastest flight from Colorado Springs to Chicago Midway Airport takes 2h 20m
Direct flights go from Colorado Springs to Chicago Midway Airport every day.
Search flight deals

  • How far is Colorado Springs to Chicago Midway by plane?

    The straight-line distance from Colorado Springs to Chicago Midway is 920.2 mi. Typically, this will take 2h 20m by plane in normal conditions.

  • When did momondo last update prices for flights from Colorado Springs Airport to Chicago Midway Airport?

    Prices for flights from Colorado Springs Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Colorado Springs Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Colorado Springs Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Colorado Springs Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Colorado Springs to Chicago Midway Airport?

  • What is the most popular airline from Colorado Springs to Chicago Midway Airport?

Best airlines flying from Colorado Springs to Chicago Midway Airport

Compare and see reviews for airlines that fly from Colorado Springs to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $227Free CancellationRating
8.0
4,333 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Benton Harbor
Portage
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Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Colorado Springs to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Colorado Springs.

Can I find flights from Colorado Springs to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Colorado Springs which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Colorado Springs to Chicago?

Once all potential Colorado Springs to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Colorado Springs to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Colorado Springs to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago Midway Airport trip

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