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Cheap flights from Colorado Springs to Chicago from $89

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 12/9. 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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Cheap round-trip flights

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Delta Logo
1:40 pm - 9:45 pmCOS-MDW
7h 05m1 stop
Delta Logo
1:05 pm - 9:22 pmMDW-COS
9h 17m1 stop
$197Delta
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Tue, Apr 14 - Wed, Apr 15
Southwest Logo
12:05 pm - 7:55 pmCOS-MDW
6h 50m1 stop
Southwest Logo
4:05 pm - 7:30 pmMDW-COS
4h 25m1 stop
$229Southwest
Find Deal
Wed, Jan 28 - Sat, Jan 31
Southwest Logo
12:05 pm - 7:55 pmCOS-MDW
6h 50m1 stop
Southwest Logo
12:00 pm - 7:30 pmMDW-COS
8h 30m2 stops
$234Southwest
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Wed, Jan 28 - Sat, Jan 31
Delta Logo
1:20 pm - 10:26 pmCOS-MDW
8h 06m1 stop
Delta Logo
6:00 am - 12:23 pmMDW-COS
7h 23m1 stop
$239Delta
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Tue, Jan 27 - Sat, Jan 31
Southwest Logo
12:05 pm - 7:55 pmCOS-MDW
6h 50m1 stop
Southwest Logo
5:20 am - 9:55 amMDW-COS
5h 35m1 stop
$264Southwest
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Wed, Jan 28 - Sun, Feb 1
Delta Logo
1:40 pm - 9:45 pmCOS-MDW
7h 05m1 stop
Delta Logo
1:05 pm - 9:22 pmMDW-COS
9h 17m1 stop
$268Delta
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Tue, Apr 14 - Wed, Apr 15
Southwest Logo
3:10 pm - 10:40 pmCOS-MDW
6h 30m1 stop
Southwest Logo
2:40 pm - 9:30 pmMDW-COS
7h 50m2 stops
$269Southwest
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Wed, Jan 28 - Sun, Feb 1
Southwest Logo
1:45 pm - 10:55 pmCOS-MDW
8h 10m2 stops
Southwest Logo
8:40 am - 3:35 pmMDW-COS
7h 55m2 stops
$274Southwest
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Wed, Jan 28 - Sat, Jan 31
Southwest Logo
6:25 am - 4:45 pmCOS-MDW
9h 20m1 stop
Southwest Logo
7:50 am - 9:30 amMDW-COS
2h 40mnonstop
$306Southwest
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Sat, Dec 6 - Sun, Dec 14
Southwest Logo
7:20 am - 4:40 pmCOS-MDW
8h 20m2 stops
Southwest Logo
2:40 pm - 9:30 pmMDW-COS
7h 50m2 stops
$309Southwest
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Wed, Jan 28 - Sun, Feb 1

Delta flights from Colorado Springs to Chicago Midway Airport

Our best Delta deals on Colorado Springs to Chicago Midway Airport flight tickets
Delta
Apr 14
COS1:40 pmColorado Springs
7h 05m
1 stop
MDW9:45 pmChicago Midway
Apr 15
MDW1:05 pmChicago Midway
9h 17m
1 stop
COS9:22 pmColorado Springs
$197
Find similar
Delta
Jan 27
COS1:20 pmColorado Springs
8h 06m
1 stop
MDW10:26 pmChicago Midway
Jan 31
MDW6:00 amChicago Midway
7h 23m
1 stop
COS12:23 pmColorado Springs
$239
Find similar
Delta
Apr 14
COS1:40 pmColorado Springs
7h 05m
1 stop
MDW9:45 pmChicago Midway
Apr 15
MDW1:05 pmChicago Midway
9h 17m
1 stop
COS9:22 pmColorado Springs
$268
Find similar

Southwest flights from Colorado Springs to Chicago Midway Airport

Our best Southwest deals on Colorado Springs to Chicago Midway Airport flight tickets
Southwest
Jan 28
COS12:05 pmColorado Springs
6h 50m
1 stop
MDW7:55 pmChicago Midway
Jan 31
MDW4:05 pmChicago Midway
4h 25m
1 stop
COS7:30 pmColorado Springs
$229
Find similar
Southwest
Jan 28
COS12:05 pmColorado Springs
6h 50m
1 stop
MDW7:55 pmChicago Midway
Jan 31
MDW12:00 pmChicago Midway
8h 30m
2 stops
COS7:30 pmColorado Springs
$234
Find similar
Southwest
Jan 28
COS12:05 pmColorado Springs
6h 50m
1 stop
MDW7:55 pmChicago Midway
Feb 1
MDW5:20 amChicago Midway
5h 35m
1 stop
COS9:55 amColorado Springs
$264
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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 November 10, 2025.
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 4/14

1:40 pm-9:45 pm

1 stop7h 05m

Chicago Midway

Wed 4/15

1:05 pm-9:22 pm

1 stop9h 17m

$197

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 1/28

12:05 pm-7:55 pm

1 stop6h 50m

Chicago Midway

Sat 1/31

4:05 pm-7:30 pm

1 stop4h 25m

$229

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 1/28

12:05 pm-7:55 pm

1 stop6h 50m

Chicago Midway

Sat 1/31

12:00 pm-7:30 pm

2 stops8h 30m

$234

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 1/27

1:20 pm-10:26 pm

1 stop8h 06m

Chicago Midway

Sat 1/31

6:00 am-12:23 pm

1 stop7h 23m

$239

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 1/28

12:05 pm-7:55 pm

1 stop6h 50m

Chicago Midway

Sun 2/1

5:20 am-9:55 am

1 stop5h 35m

$264

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 4/14

1:40 pm-9:45 pm

1 stop7h 05m

Chicago Midway

Wed 4/15

1:05 pm-9:22 pm

1 stop9h 17m

$268

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 1/28

3:10 pm-10:40 pm

1 stop6h 30m

Chicago Midway

Sun 2/1

2:40 pm-9:30 pm

2 stops7h 50m

$269

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 1/28

1:45 pm-10:55 pm

2 stops8h 10m

Chicago Midway

Sat 1/31

8:40 am-3:35 pm

2 stops7h 55m

$274

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 12/6

6:25 am-4:45 pm

1 stop9h 20m

Chicago Midway

Sun 12/14

7:50 am-9:30 am

Nonstop2h 40m

$306

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 1/28

7:20 am-4:40 pm

2 stops8h 20m

Chicago Midway

Sun 2/1

2:40 pm-9:30 pm

2 stops7h 50m

$309

Flights are sorted by cheapest round-trip flights 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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado Springs, with most prices found around $280. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Colorado Springs during the month August is also very affordable. Most momondo users find prices during this month for around $281.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Colorado Springs. The lowest ticket price found for a Friday departure recently was $224. 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 $290.

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 $173 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $313. 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?

You could potentially save up to 1% on your flight if you consider stops on a Colorado Springs to Chicago Midway Airport flight.

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

$223

Fastest flight time

2h 20m

Direct flights

Mon, Tue, Wed, Thu, Sat and Sun
The best one-way flight to Chicago Midway Airport from Colorado Springs in the past 72 hours is $223. The best round-trip flight deal from Colorado Springs to Chicago Midway Airport found on momondo in the last 72 hours is $340.
The fastest flight from Colorado Springs to Chicago Midway Airport takes 2h 20m
Direct flights go from Colorado Springs to Chicago Midway Airport on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. The only airline offering direct flights is Southwest.
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  • 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
4,235 reviews
Search Southwest flights

  • Southwest Flights From Colorado Springs to Chicago Midway Airport

    Southwest operates around 4 flights from Colorado Springs to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $321, but momondo users have found Southwest deals from Colorado Springs to Chicago Midway Airport from as low as $233 round-trip. Southwest has been scored 8.0/10 in 4,235 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Valparaiso
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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.

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