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Cheap flights from Colorado Springs to Chicago from $125

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 3/3. 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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Find the cheapest flights from Colorado Springs to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:45 pm - 8:40 pm
COS
-
MDW
5h 55m
1 stop
Southwest Logo
6:30 am - 12:55 pm
MDW
-
COS
7h 25m
1 stop
$249Southwest
Tue, Mar 3 - Tue, Mar 10
Delta Logo
1:22 pm - 10:33 pm
COS
-
MDW
8h 11m
1 stop
Delta Logo
1:10 pm - 10:05 pm
MDW
-
COS
9h 55m
2 stops
$254Delta
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
10:35 am - 5:10 pm
COS
-
MDW
5h 35m
1 stop
Southwest Logo
5:55 am - 9:25 am
MDW
-
COS
4h 30m
1 stop
$260Southwest
Mon, Mar 2 - Sat, Mar 14
Southwest Logo
7:20 pm - 5:00 am
COS
-
MDW
8h 40m
1 stop
Southwest Logo
6:10 am - 12:00 pm
MDW
-
COS
6h 50m
1 stop
$266Southwest
Thu, Apr 9 - Tue, Apr 14
Southwest Logo
7:20 pm - 5:00 am
COS
-
MDW
8h 40m
1 stop
Southwest Logo
8:15 am - 3:30 pm
MDW
-
COS
8h 15m
2 stops
$271Southwest
Thu, Apr 9 - Tue, Apr 14
Southwest Logo
10:40 am - 5:30 pm
COS
-
MDW
5h 50m
1 stop
Southwest Logo
5:55 am - 9:30 am
MDW
-
COS
4h 35m
1 stop
$274Southwest
Thu, Mar 5 - Tue, Mar 10
Southwest Logo
10:40 am - 8:20 pm
COS
-
MDW
8h 40m
2 stops
Southwest Logo
5:50 pm - 11:35 pm
MDW
-
COS
6h 45m
1 stop
$279Southwest
Thu, Mar 5 - Tue, Mar 10
Southwest Logo
10:35 am - 5:10 pm
COS
-
MDW
5h 35m
1 stop
Southwest Logo
5:40 am - 2:40 pm
MDW
-
COS
10h 00m
2 stops
$283Southwest
Mon, Mar 2 - Sat, Mar 14
Southwest Logo
8:00 pm - 5:00 am
COS
-
MDW
8h 00m
2 stops
Southwest Logo
10:15 am - 3:30 pm
MDW
-
COS
6h 15m
2 stops
$298Southwest
Thu, Apr 9 - Tue, Apr 14
Delta Logo
1:22 pm - 10:31 pm
COS
-
MDW
8h 09m
1 stop
Delta Logo
6:00 am - 12:25 pm
MDW
-
COS
7h 25m
1 stop
$299Delta
Sat, Feb 14 - Tue, Feb 17

Delta flights from Colorado Springs to Chicago Midway Airport

Our best Delta deals on Colorado Springs to Chicago Midway Airport flight tickets
Delta
Feb 17
COS1:22 pmColorado Springs
8h 11m
1 stop
MDW10:33 pmChicago Midway
Feb 24
MDW6:00 amChicago Midway
7h 25m
1 stop
COS12:25 pmColorado Springs
$274
Delta
Feb 14
COS1:22 pmColorado Springs
8h 09m
1 stop
MDW10:31 pmChicago Midway
Feb 17
MDW6:00 amChicago Midway
7h 25m
1 stop
COS12:25 pmColorado Springs
$299
Delta
Feb 14
COS7:55 amColorado Springs
13h 36m
2 stops
MDW10:31 pmChicago Midway
Feb 17
MDW6:00 amChicago Midway
7h 25m
1 stop
COS12:25 pmColorado Springs
$334

Southwest flights from Colorado Springs to Chicago Midway Airport

Our best Southwest deals on Colorado Springs to Chicago Midway Airport flight tickets
Southwest
Mar 3
COS1:45 pmColorado Springs
5h 55m
1 stop
MDW8:40 pmChicago Midway
Mar 10
MDW6:30 amChicago Midway
7h 25m
1 stop
COS12:55 pmColorado Springs
$249
Southwest
Mar 3
COS7:20 amColorado Springs
8h 15m
2 stops
MDW4:35 pmChicago Midway
Mar 10
MDW5:50 pmChicago Midway
6h 45m
1 stop
COS11:35 pmColorado Springs
$254
Southwest
Mar 2
COS10:35 amColorado Springs
5h 35m
1 stop
MDW5:10 pmChicago Midway
Mar 14
MDW5:55 amChicago Midway
4h 30m
1 stop
COS9:25 amColorado Springs
$260

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 February 3, 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

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 3/3

1:45 pm-8:40 pm

1 stop5h 55m

Chicago Midway

Tue 3/10

6:30 am-12:55 pm

1 stop7h 25m

$249

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 3/3

1:22 pm-10:33 pm

1 stop8h 11m

Chicago Midway

Tue 3/10

1:10 pm-10:05 pm

2 stops9h 55m

$254

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Mon 3/2

10:35 am-5:10 pm

1 stop5h 35m

Chicago Midway

Sat 3/14

5:55 am-9:25 am

1 stop4h 30m

$260

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/9

7:20 pm-5:00 am

1 stop8h 40m

Chicago Midway

Tue 4/14

6:10 am-12:00 pm

1 stop6h 50m

$266

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/9

7:20 pm-5:00 am

1 stop8h 40m

Chicago Midway

Tue 4/14

8:15 am-3:30 pm

2 stops8h 15m

$271

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 3/5

10:40 am-5:30 pm

1 stop5h 50m

Chicago Midway

Tue 3/10

5:55 am-9:30 am

1 stop4h 35m

$274

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 3/5

10:40 am-8:20 pm

2 stops8h 40m

Chicago Midway

Tue 3/10

5:50 pm-11:35 pm

1 stop6h 45m

$279

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Mon 3/2

10:35 am-5:10 pm

1 stop5h 35m

Chicago Midway

Sat 3/14

5:40 am-2:40 pm

2 stops10h 00m

$283

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/9

8:00 pm-5:00 am

2 stops8h 00m

Chicago Midway

Tue 4/14

10:15 am-3:30 pm

2 stops6h 15m

$298

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 2/14

1:22 pm-10:31 pm

1 stop8h 09m

Chicago Midway

Tue 2/17

6:00 am-12:25 pm

1 stop7h 25m

$299

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 cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado Springs, with most prices found around $283. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Colorado Springs during the month January is also very affordable. Most momondo users find prices during this month for around $284.

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

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Colorado Springs. The lowest ticket price found for a Monday departure recently was $225. 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 $294.

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

Flying to Chicago Midway Airport from Colorado Springs in the evening is the least expensive time of day to depart. momondo users have found prices as low as $190 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $327. 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

Fastest flight time

2h 20m

Direct flights

Wed, Thu, Sat and Sun
The fastest flight from Colorado Springs to Chicago Midway Airport takes 2h 20m
Direct flights go from Colorado Springs to Chicago Midway Airport on Wednesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.
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 $233Free CancellationRating
8.0
4,272 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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Portage
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Schererville
Valparaiso
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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