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Cheap flights from Colorado Springs to Chicago from $112

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 10/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Colorado Springs to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:27 am - 6:01 pm
COS
-
MDW
5h 34m
1 stop
Delta Logo
6:11 am - 12:15 pm
MDW
-
COS
7h 04m
1 stop
$291Delta
Tue, Aug 25 - Sat, Aug 29
Delta Logo
6:00 am - 6:33 pm
COS
-
MDW
11h 33m
2 stops
Delta Logo
6:11 am - 12:15 pm
MDW
-
COS
7h 04m
1 stop
$296Delta
Tue, Aug 25 - Sat, Aug 29
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
5:40 am - 10:45 am
MDW
-
COS
6h 05m
1 stop
$305Southwest
Tue, Aug 11 - Thu, Aug 13
Southwest Logo
6:15 am - 12:00 pm
COS
-
MDW
4h 45m
1 stop
Southwest Logo
7:10 am - 2:15 pm
MDW
-
COS
8h 05m
1 stop
$310Southwest
Tue, Aug 11 - Thu, Aug 13
Delta Logo
11:27 am - 6:01 pm
COS
-
MDW
5h 34m
1 stop
Delta Logo
6:11 am - 12:15 pm
MDW
-
COS
7h 04m
1 stop
$315Delta
Tue, Aug 25 - Sat, Aug 29
Southwest Logo
6:15 am - 12:00 pm
COS
-
MDW
4h 45m
1 stop
Southwest Logo
10:05 am - 6:05 pm
MDW
-
COS
9h 00m
2 stops
$316Southwest
Tue, Aug 11 - Thu, Aug 13
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
4:30 pm - 6:00 pm
MDW
-
COS
2h 30mnonstop
$318Southwest
Wed, Aug 26 - Sun, Sep 6
Delta Logo
6:00 am - 6:33 pm
COS
-
MDW
11h 33m
2 stops
Delta Logo
6:11 am - 12:15 pm
MDW
-
COS
7h 04m
1 stop
$320Delta
Tue, Aug 25 - Sat, Aug 29
Southwest Logo
1:15 pm - 9:50 pm
COS
-
MDW
7h 35m
2 stops
Southwest Logo
4:30 pm - 6:00 pm
MDW
-
COS
2h 30mnonstop
$321Southwest
Wed, Aug 26 - Sun, Sep 6
Southwest Logo
1:15 pm - 10:20 pm
COS
-
MDW
8h 05m
2 stops
Southwest Logo
10:05 am - 6:05 pm
MDW
-
COS
9h 00m
2 stops
$325Southwest
Tue, Aug 11 - Thu, Aug 13

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Delta flights from Colorado Springs to Chicago Midway Airport

Our best Delta deals on Colorado Springs to Chicago Midway Airport flight tickets
Delta
Aug 25
COS11:27 amColorado Springs
5h 34m
1 stop
MDW6:01 pmChicago Midway
Aug 29
MDW6:11 amChicago Midway
7h 04m
1 stop
COS12:15 pmColorado Springs
$291
Delta
Aug 25
COS6:00 amColorado Springs
11h 33m
2 stops
MDW6:33 pmChicago Midway
Aug 29
MDW6:11 amChicago Midway
7h 04m
1 stop
COS12:15 pmColorado Springs
$296
Delta
Aug 25
COS11:27 amColorado Springs
5h 34m
1 stop
MDW6:01 pmChicago Midway
Aug 29
MDW6:11 amChicago Midway
7h 04m
1 stop
COS12:15 pmColorado Springs
$315

Southwest flights from Colorado Springs to Chicago Midway Airport

Our best Southwest deals on Colorado Springs to Chicago Midway Airport flight tickets
Southwest
Aug 15
COS2:00 pmColorado Springs
7h 15m
1 stop
MDW10:15 pmChicago Midway
Aug 18
MDW3:35 pmChicago Midway
2h 25m
COS5:00 pmColorado Springs
$227
Southwest
Aug 15
COS2:00 pmColorado Springs
7h 15m
1 stop
MDW10:15 pmChicago Midway
Aug 18
MDW9:25 amChicago Midway
7h 15m
1 stop
COS3:40 pmColorado Springs
$237
Southwest
Aug 15
COS2:00 pmColorado Springs
7h 15m
1 stop
MDW10:15 pmChicago Midway
Aug 18
MDW3:10 pmChicago Midway
7h 35m
2 stops
COS9:45 pmColorado Springs
$242

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 July 7, 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

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

11:27 am-6:01 pm

1 stop5h 34m

Chicago Midway

Sat 8/29

6:11 am-12:15 pm

1 stop7h 04m

$291

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

6:00 am-6:33 pm

2 stops11h 33m

Chicago Midway

Sat 8/29

6:11 am-12:15 pm

1 stop7h 04m

$296

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/11

1:15 pm-4:35 pm

Nonstop2h 20m

Chicago Midway

Thu 8/13

5:40 am-10:45 am

1 stop6h 05m

$305

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/11

6:15 am-12:00 pm

1 stop4h 45m

Chicago Midway

Thu 8/13

7:10 am-2:15 pm

1 stop8h 05m

$310

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

11:27 am-6:01 pm

1 stop5h 34m

Chicago Midway

Sat 8/29

6:11 am-12:15 pm

1 stop7h 04m

$315

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/11

6:15 am-12:00 pm

1 stop4h 45m

Chicago Midway

Thu 8/13

10:05 am-6:05 pm

2 stops9h 00m

$316
Quickest round-trip

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 8/26

1:15 pm-4:35 pm

Nonstop2h 20m

Chicago Midway

Sun 9/6

4:30 pm-6:00 pm

Nonstop2h 30m

$318

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

6:00 am-6:33 pm

2 stops11h 33m

Chicago Midway

Sat 8/29

6:11 am-12:15 pm

1 stop7h 04m

$320

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 8/26

1:15 pm-9:50 pm

2 stops7h 35m

Chicago Midway

Sun 9/6

4:30 pm-6:00 pm

Nonstop2h 30m

$321

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/11

1:15 pm-10:20 pm

2 stops8h 05m

Chicago Midway

Thu 8/13

10:05 am-6:05 pm

2 stops9h 00m

$325

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 April is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado Springs, with most prices found around $288. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Colorado Springs during the month January is also very affordable. Most momondo users find prices during this month for around $298.

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 $332. 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 $623.

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 $401 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $482. 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 Airport flights?

There is only 1 cabin class available to choose from on Colorado Springs to Chicago Midway Airport 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

$244

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Colorado Springs in the past 72 hours is $244. The best round-trip flight deal from Colorado Springs to Chicago Midway Airport found on momondo in the last 72 hours is $373.
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

Frequently asked questions about flying from Colorado Springs to Chicago Midway Airport

  • 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
7.9
4,250 reviews
Search Southwest flights

  • Southwest Flights From Colorado Springs to Chicago Midway Airport

    Southwest operates around 5 flights from Colorado Springs to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $381, but momondo users have found Southwest deals from Colorado Springs to Chicago Midway Airport from as low as $227 round-trip. Southwest has been scored 7.9/10 in 4,250 reviews.

Traveling to a place near Chicago?

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