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Cheap flights from Colorado Springs to Chicago from $176

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 10/7. 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
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
10:10 am - 11:40 am
MDW
-
COS
2h 30mnonstop
$351Southwest
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
6:15 am - 12:00 pm
COS
-
MDW
4h 45m
1 stop
Southwest Logo
10:10 am - 11:40 am
MDW
-
COS
2h 30mnonstop
$357Southwest
Wed, Sep 9 - Sat, Sep 12
Southwest Logo
12:20 pm - 11:25 pm
COS
-
MDW
10h 05m
1 stop
Southwest Logo
12:30 pm - 2:00 pm
MDW
-
COS
2h 30mnonstop
$361Southwest
Fri, Jun 26 - Fri, Jul 3
Southwest Logo
12:20 pm - 12:35 am
COS
-
MDW
11h 15m
2 stops
Southwest Logo
12:30 pm - 2:00 pm
MDW
-
COS
2h 30mnonstop
$366Southwest
Fri, Jun 26 - Fri, Jul 3
Delta Logo
11:27 am - 6:01 pm
COS
-
MDW
5h 34m
1 stop
Delta Logo
6:05 am - 12:15 pm
MDW
-
COS
7h 10m
1 stop
$371Delta
Tue, Aug 25 - Sat, Aug 29
Southwest Logo
6:15 am - 12:00 pm
COS
-
MDW
4h 45m
1 stop
Southwest Logo
1:45 pm - 8:35 pm
MDW
-
COS
7h 50m
2 stops
$372Southwest
Tue, Sep 1 - Sat, Sep 5
Delta Logo
1:40 pm - 10:17 pm
COS
-
MDW
7h 37m
1 stop
Delta Logo
1:18 pm - 10:41 pm
MDW
-
COS
10h 23m
2 stops
$376Delta
Thu, Jul 2 - Tue, Jul 14
Southwest Logo
2:40 pm - 6:00 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
8:30 am - 4:45 pm
MDW
-
COS
9h 15m
1 stop
$377Southwest
Thu, Jul 2 - Sun, Jul 12
Southwest Logo
4:55 pm - 12:10 am
COS
-
MDW
6h 15m
1 stop
Southwest Logo
6:40 pm - 1:20 am
MDW
-
COS
7h 40m
1 stop
$381Southwest
Fri, Jun 12 - Fri, Jun 19
Delta Logo
6:00 am - 6:01 pm
COS
-
MDW
11h 01m
2 stops
Delta Logo
9:24 am - 5:36 pm
MDW
-
COS
9h 12m
2 stops
$382Delta
Tue, Aug 25 - Sat, Aug 29

Southwest flights from Colorado Springs to Chicago Midway Airport

Our best Southwest deals on Colorado Springs to Chicago Midway Airport flight tickets
Southwest
Aug 20
COS1:15 pmColorado Springs
2h 20m
MDW4:35 pmChicago Midway
Aug 22
MDW10:10 amChicago Midway
2h 30m
COS11:40 amColorado Springs
$351
Southwest
Sep 9
COS6:15 amColorado Springs
4h 45m
1 stop
MDW12:00 pmChicago Midway
Sep 12
MDW10:10 amChicago Midway
2h 30m
COS11:40 amColorado Springs
$357
Southwest
Jun 26
COS12:20 pmColorado Springs
10h 05m
1 stop
MDW11:25 pmChicago Midway
Jul 3
MDW12:30 pmChicago Midway
2h 30m
COS2:00 pmColorado Springs
$361

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
MDW6:05 amChicago Midway
7h 10m
1 stop
COS12:15 pmColorado Springs
$371
Delta
Jul 2
COS1:40 pmColorado Springs
7h 37m
1 stop
MDW10:17 pmChicago Midway
Jul 14
MDW1:18 pmChicago Midway
10h 23m
2 stops
COS10:41 pmColorado Springs
$376
Delta
Aug 25
COS6:00 amColorado Springs
11h 33m
2 stops
MDW6:33 pmChicago Midway
Aug 28
MDW6:05 amChicago Midway
12h 31m
2 stops
COS5:36 pmColorado Springs
$382

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 May 16, 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

Thu 8/20

1:15 pm-4:35 pm

Nonstop2h 20m

Chicago Midway

Sat 8/22

10:10 am-11:40 am

Nonstop2h 30m

$351

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 9/9

6:15 am-12:00 pm

1 stop4h 45m

Chicago Midway

Sat 9/12

10:10 am-11:40 am

Nonstop2h 30m

$357

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 6/26

12:20 pm-11:25 pm

1 stop10h 05m

Chicago Midway

Fri 7/3

12:30 pm-2:00 pm

Nonstop2h 30m

$361

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 6/26

12:20 pm-12:35 am

2 stops11h 15m

Chicago Midway

Fri 7/3

12:30 pm-2:00 pm

Nonstop2h 30m

$366

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

11:27 am-6:01 pm

1 stop5h 34m

Chicago Midway

Sat 8/29

6:05 am-12:15 pm

1 stop7h 10m

$371

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 9/1

6:15 am-12:00 pm

1 stop4h 45m

Chicago Midway

Sat 9/5

1:45 pm-8:35 pm

2 stops7h 50m

$372

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 7/2

1:40 pm-10:17 pm

1 stop7h 37m

Chicago Midway

Tue 7/14

1:18 pm-10:41 pm

2 stops10h 23m

$376

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 7/2

2:40 pm-6:00 pm

Nonstop2h 20m

Chicago Midway

Sun 7/12

8:30 am-4:45 pm

1 stop9h 15m

$377

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 6/12

4:55 pm-12:10 am

1 stop6h 15m

Chicago Midway

Fri 6/19

6:40 pm-1:20 am

1 stop7h 40m

$381

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 8/25

6:00 am-6:01 pm

2 stops11h 01m

Chicago Midway

Sat 8/29

9:24 am-5:36 pm

2 stops9h 12m

$382

Flights are sorted by cheapest round-trip flights first.

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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 month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Colorado Springs, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Colorado Springs during the month April is also very affordable. Most momondo users find prices during this month for around $240.

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 $298. 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, Tuesday 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 $492.

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 $381 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $472. 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

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

$229

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 $229. The best round-trip flight deal from Colorado Springs to Chicago Midway Airport found on momondo in the last 72 hours is $404.
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
8.0
4,295 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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