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Cheap flights from Colorado Springs to Chicago from $104

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 12/14. 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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0 bags

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Cheap round-trip flights

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American Airlines Logo
12:36 pm - 4:22 pmCOS-ORD
2h 46mnonstop
American Airlines Logo
9:55 am - 12:02 pmORD-COS
3h 07mnonstop
$261American Airlines
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Tue, Dec 2 - Tue, Dec 9
United Airlines Logo
4:45 pm - 11:59 pmCOS-ORD
6h 14m1 stop
United Airlines Logo
9:20 am - 11:26 amORD-COS
3h 06mnonstop
$271United Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
American Airlines Logo
12:36 pm - 4:22 pmCOS-ORD
2h 46mnonstop
American Airlines Logo
9:55 am - 12:02 pmORD-COS
3h 07mnonstop
$279American Airlines
Find Deal
Mon, Nov 24 - Thu, Dec 4
Southwest Logo
8:55 am - 5:05 pmCOS-MDW
7h 10m1 stop
Southwest Logo
1:20 pm - 7:40 pmMDW-COS
7h 20m1 stop
$281Southwest
Find Deal
Tue, Dec 2 - Tue, Dec 9
United Airlines Logo
6:00 am - 11:29 amCOS-ORD
4h 29m1 stop
United Airlines Logo
2:40 pm - 9:00 pmORD-COS
7h 20m1 stop
$281United Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Southwest Logo
8:55 am - 5:05 pmCOS-MDW
7h 10m1 stop
Southwest Logo
5:00 am - 11:40 amMDW-COS
7h 40m2 stops
$286Southwest
Find Deal
Tue, Dec 2 - Tue, Dec 9
Delta Logo
6:00 am - 3:20 pmCOS-ORD
8h 20m1 stop
Delta Logo
11:15 am - 10:25 pmORD-COS
12h 10m2 stops
$286Delta
Find Deal
Tue, Dec 2 - Tue, Dec 9
American Airlines Logo
12:36 pm - 4:22 pmCOS-ORD
2h 46mnonstop
American Airlines Logo
8:11 am - 3:41 pmORD-COS
8h 30m1 stop
$289American Airlines
Find Deal
Mon, Nov 24 - Thu, Dec 4
Southwest Logo
8:55 am - 7:10 pmCOS-MDW
9h 15m2 stops
Southwest Logo
11:25 am - 7:40 pmMDW-COS
9h 15m2 stops
$291Southwest
Find Deal
Tue, Dec 2 - Tue, Dec 9
Delta Logo
1:42 pm - 10:43 pmCOS-ORD
8h 01m1 stop
Delta Logo
10:05 am - 10:25 pmORD-COS
13h 20m2 stops
$321Delta
Find Deal
Tue, Dec 16 - Sun, Dec 21

United Airlines flights from Colorado Springs to Chicago

Our best United Airlines deals on Colorado Springs to Chicago flight tickets
United Airlines
Dec 2
COS4:45 pmColorado Springs
6h 14m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 9
ORD9:20 amChicago O'Hare Intl
3h 06m
COS11:26 amColorado Springs
$271
Find similar
United Airlines
Dec 2
COS6:00 amColorado Springs
4h 29m
1 stop
ORD11:29 amChicago O'Hare Intl
Dec 9
ORD2:40 pmChicago O'Hare Intl
7h 20m
1 stop
COS9:00 pmColorado Springs
$281
Find similar
United Airlines
Dec 17
COS9:24 amColorado Springs
2h 51m
ORD1:15 pmChicago O'Hare Intl
Dec 20
ORD9:12 amChicago O'Hare Intl
3h 12m
COS11:24 amColorado Springs
$296
Find similar

American Airlines flights from Colorado Springs to Chicago

Our best American Airlines deals on Colorado Springs to Chicago flight tickets
American Airlines
Dec 2
COS12:36 pmColorado Springs
2h 46m
ORD4:22 pmChicago O'Hare Intl
Dec 9
ORD9:55 amChicago O'Hare Intl
3h 07m
COS12:02 pmColorado Springs
$261
Find similar
American Airlines
Nov 24
COS12:36 pmColorado Springs
2h 46m
ORD4:22 pmChicago O'Hare Intl
Dec 4
ORD9:55 amChicago O'Hare Intl
3h 07m
COS12:02 pmColorado Springs
$279
Find similar
American Airlines
Nov 24
COS12:36 pmColorado Springs
2h 46m
ORD4:22 pmChicago O'Hare Intl
Dec 4
ORD8:11 amChicago O'Hare Intl
8h 30m
1 stop
COS3:41 pmColorado Springs
$289
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Colorado Springs to Chicago 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 3, 2025.
Use the filters below to find and compare flights from Colorado Springs to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 12/2

12:36 pm-4:22 pm

Nonstop2h 46m

Chicago O'Hare Intl

Tue 12/9

9:55 am-12:02 pm

Nonstop3h 07m

$261

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 12/2

4:45 pm-11:59 pm

1 stop6h 14m

Chicago O'Hare Intl

Tue 12/9

9:20 am-11:26 am

Nonstop3h 06m

$271

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Mon 11/24

12:36 pm-4:22 pm

Nonstop2h 46m

Chicago O'Hare Intl

Thu 12/4

9:55 am-12:02 pm

Nonstop3h 07m

$279

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 12/2

8:55 am-5:05 pm

1 stop7h 10m

Chicago Midway

Tue 12/9

1:20 pm-7:40 pm

1 stop7h 20m

$281

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 12/2

6:00 am-11:29 am

1 stop4h 29m

Chicago O'Hare Intl

Tue 12/9

2:40 pm-9:00 pm

1 stop7h 20m

$281

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 12/2

8:55 am-5:05 pm

1 stop7h 10m

Chicago Midway

Tue 12/9

5:00 am-11:40 am

2 stops7h 40m

$286

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 12/2

6:00 am-3:20 pm

1 stop8h 20m

Chicago O'Hare Intl

Tue 12/9

11:15 am-10:25 pm

2 stops12h 10m

$286

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Mon 11/24

12:36 pm-4:22 pm

Nonstop2h 46m

Chicago O'Hare Intl

Thu 12/4

8:11 am-3:41 pm

1 stop8h 30m

$289

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 12/2

8:55 am-7:10 pm

2 stops9h 15m

Chicago Midway

Tue 12/9

11:25 am-7:40 pm

2 stops9h 15m

$291

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 12/16

1:42 pm-10:43 pm

1 stop8h 01m

Chicago O'Hare Intl

Sun 12/21

10:05 am-10:25 pm

2 stops13h 20m

$321

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

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?

The month of February is, on average, the cheapest month to fly to Chicago from Colorado Springs, with most prices found around $309. If you’re not able to fly to Chicago in February, then August is your next best option. Flight prices from Colorado Springs to Chicago during August average around $311.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $303. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Colorado Springs to Chicago for around $506.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Colorado Springs to Chicago during this time can be as low as $197. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $628.

What is the cheapest Colorado Springs to Chicago flight route?

Fly from Colorado Springs to Chicago Midway for the best Colorado Springs - Chicago flight prices

What cabin class options are available on Colorado Springs to Chicago flights?

There are 4 cabin classes available to choose from on Colorado Springs to Chicago 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 flights?

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

How have Colorado Springs to Chicago flight prices changed over time?

As of November 2025, prices for Colorado Springs to Chicago flights are approximately 12% more expensive when compared to flights at the same time last year.

When to book flights from Colorado Springs to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Colorado Springs to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Colorado Springs to Chicago (COS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Colorado Springs to Chicago

Best Price Found

$178

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Colorado Springs in the past 72 hours is $178. The best round-trip flight deal from Colorado Springs to Chicago found on momondo in the last 72 hours is $340.
The fastest flight from Colorado Springs to Chicago takes 2h 20m
Direct flights go from Colorado Springs to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • How far is Colorado Springs to Chicago by plane?

    Colorado Springs and Chicago are 927.0 mi apart from one another. 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?

    Prices for flights from Colorado Springs Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Colorado Springs Airport to Chicago?

  • How old do you have to be to fly from Colorado Springs Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Colorado Springs Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Colorado Springs to Chicago?

  • What is the most popular airline from Colorado Springs to Chicago?

Best airlines flying from Colorado Springs to Chicago

Compare and see reviews for airlines that fly from Colorado Springs to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $223Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
SouthwestPriceFrom $233Free CancellationRating
8.0
4,238 reviews
Search Southwest flights
United AirlinesPriceFrom $290Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights

  • Southwest Flights From Colorado Springs to Chicago

    Across 4 Southwest flights from Colorado Springs to Chicago this week, the average price was $321, with the best Southwest deals starting from $233 round-trip. 4,238 users have rated Southwest on momondo, with an average score of 8.0/10.

  • United Airlines Flights From Colorado Springs to Chicago

    United Airlines (7.4/10 from 8,997 reviews) operates around 11 flights from Colorado Springs to Chicago in any given week. The average United Airlines airfare for this route is around $400, with deals from around $290 rare but found on momondo. Referenced prices are for round-trip Colorado Springs to Chicago flight searches in the last 72 hours.

Traveling to a place near Chicago?

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

Why use momondo?

Why should I use momondo to find a flight deal from Colorado Springs to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Colorado Springs to Chicago for you.

Can I find flights from Colorado Springs to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Colorado Springs with this policy.

How can momondo help me find flights from Colorado Springs to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Colorado Springs to Chicago.

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport