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Cheap flights from Colorado Springs to Chicago from $139

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.
Southwest Logo
12:40 pm - 4:00 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
3:35 pm - 5:10 pmMDW  Chicago Midway-COS Colorado Springs
2h 35mnonstop
$277Southwest
Wed, Oct 14 - Wed, Oct 21
Southwest Logo
12:40 pm - 4:00 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
5:45 am - 11:05 amMDW  Chicago Midway-COS Colorado Springs
6h 20m1 stop Phoenix Sky Harbor Intl
$287Southwest
Tue, Oct 6 - Wed, Oct 14
Southwest Logo
4:20 pm - 11:50 pmCOS  Colorado Springs-MDW Chicago Midway
6h 30m1 stop Denver Intl
Southwest Logo
3:35 pm - 5:00 pmMDW  Chicago Midway-COS Colorado Springs
2h 25mnonstop
$287Southwest
Mon, Sep 21 - Wed, Sep 23
Southwest Logo
12:40 pm - 4:00 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:00 am - 10:35 amMDW  Chicago Midway-COS Colorado Springs
5h 35m1 stop Dallas Love Field
$287Southwest
Wed, Oct 14 - Wed, Oct 21
Southwest Logo
12:40 pm - 4:00 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:05 am - 12:00 pmMDW  Chicago Midway-COS Colorado Springs
6h 55m1 stop Las Vegas Harry Reid Intl
$287Southwest
Wed, Oct 14 - Wed, Oct 21
Southwest Logo
12:40 pm - 4:00 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:05 am - 9:45 amMDW  Chicago Midway-COS Colorado Springs
4h 40m1 stop Denver Intl
$287Southwest
Tue, Oct 6 - Tue, Oct 13
Southwest Logo
12:40 pm - 4:00 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:05 am - 9:45 amMDW  Chicago Midway-COS Colorado Springs
4h 40m1 stop Denver Intl
$287Southwest
Wed, Oct 7 - Wed, Oct 14
Southwest Logo
1:15 pm - 4:30 pmCOS  Colorado Springs-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
3:35 pm - 5:00 pmMDW  Chicago Midway-COS Colorado Springs
2h 25mnonstop
$291Southwest
Fri, Sep 25 - Tue, Sep 29
Delta Logo
1:26 pm - 10:33 pmCOS  Colorado Springs-MDW Chicago Midway
8h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 8:27 pmMDW  Chicago Midway-COS Colorado Springs
8h 27m1 stop Atlanta Hartsfield-Jackson
$297Delta
Sat, Nov 7 - Tue, Nov 10
Delta Logo
11:22 am - 6:19 pmCOS  Colorado Springs-MDW Chicago Midway
5h 57m1 stop Minneapolis St Paul
Delta Logo
1:00 pm - 7:56 pmMDW  Chicago Midway-COS Colorado Springs
7h 56m1 stop Atlanta Hartsfield-Jackson
$297Delta
Wed, Sep 9 - Tue, Sep 15

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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
Nov 7
COS1:26 pmColorado Springs
8h 07m
1 stop
MDW10:33 pmChicago Midway
Nov 10
MDW1:00 pmChicago Midway
8h 27m
1 stop
COS8:27 pmColorado Springs
$297
Delta
Nov 7
COS1:26 pmColorado Springs
8h 07m
1 stop
MDW10:33 pmChicago Midway
Nov 10
MDW1:22 pmChicago Midway
8h 05m
2 stops
COS8:27 pmColorado Springs
$302
Delta
Nov 7
COS6:00 amColorado Springs
11h 00m
2 stops
MDW6:00 pmChicago Midway
Nov 10
MDW10:22 amChicago Midway
11h 05m
2 stops
COS8:27 pmColorado Springs
$307

Southwest flights from Colorado Springs to Chicago Midway Airport

Our best Southwest deals on Colorado Springs to Chicago Midway Airport flight tickets
Southwest
Oct 14
COS12:40 pmColorado Springs
2h 20m
MDW4:00 pmChicago Midway
Oct 21
MDW3:35 pmChicago Midway
2h 35m
COS5:10 pmColorado Springs
$277
Southwest
Oct 6
COS12:40 pmColorado Springs
2h 20m
MDW4:00 pmChicago Midway
Oct 13
MDW6:05 amChicago Midway
4h 40m
1 stop
COS9:45 amColorado Springs
$287
Southwest
Sep 25
COS1:15 pmColorado Springs
2h 15m
MDW4:30 pmChicago Midway
Sep 29
MDW3:35 pmChicago Midway
2h 25m
COS5:00 pmColorado Springs
$291

momondo Fare Finder

 
Use the filters below to find and compare flights from Colorado Springs to Chicago Midway Airport that are best for you.

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Route

Depart

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Price

Cheapest round-trip

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Wed 10/14

12:40 pm-4:00 pm

Nonstop2h 20m

Chicago Midway

Wed 10/21

3:35 pm-5:10 pm

Nonstop2h 35m

$277

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Tue 10/6

12:40 pm-4:00 pm

Nonstop2h 20m

Chicago Midway

Wed 10/14

5:45 am-11:05 am

1 stop6h 20m

$287

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Mon 9/21

4:20 pm-11:50 pm

1 stop6h 30m

Chicago Midway

Wed 9/23

3:35 pm-5:00 pm

Nonstop2h 25m

$287

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Wed 10/14

12:40 pm-4:00 pm

Nonstop2h 20m

Chicago Midway

Wed 10/21

6:00 am-10:35 am

1 stop5h 35m

$287

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Wed 10/14

12:40 pm-4:00 pm

Nonstop2h 20m

Chicago Midway

Wed 10/21

6:05 am-12:00 pm

1 stop6h 55m

$287

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Tue 10/6

12:40 pm-4:00 pm

Nonstop2h 20m

Chicago Midway

Tue 10/13

6:05 am-9:45 am

1 stop4h 40m

$287

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Wed 10/7

12:40 pm-4:00 pm

Nonstop2h 20m

Chicago Midway

Wed 10/14

6:05 am-9:45 am

1 stop4h 40m

$287
Quickest round-trip

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Fri 9/25

1:15 pm-4:30 pm

Nonstop2h 15m

Chicago Midway

Tue 9/29

3:35 pm-5:00 pm

Nonstop2h 25m

$291

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Sat 11/7

1:26 pm-10:33 pm

1 stop8h 07m

Chicago Midway

Tue 11/10

1:00 pm-8:27 pm

1 stop8h 27m

$297

Colorado SpringsChicago

COS Colorado Springs - MDW Chicago Midway

COSMDW

Colorado Springs

Wed 9/9

11:22 am-6:19 pm

1 stop5h 57m

Chicago Midway

Tue 9/15

1:00 pm-7:56 pm

1 stop7h 56m

$297

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, Saturday is the cheapest day to fly to Chicago Midway Airport from Colorado Springs. The lowest ticket price found for a Saturday departure recently was $402. 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 $637.

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 $455 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $492. 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?

You could potentially save up to 6% 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

$139

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 $139. The best round-trip flight deal from Colorado Springs to Chicago Midway Airport found on momondo in the last 72 hours is $277.
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 $233Free CancellationRating
8.0
4,217 reviews
Search Southwest flights

  • Southwest Flights From Colorado Springs to Chicago Midway Airport

    Southwest operates around 7 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 $233 round-trip. Southwest has been scored 8.0/10 in 4,217 reviews.

Traveling to a place near Chicago?

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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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