How many flights depart from Colorado Springs to Chicago on average per week?

As of September 2025, there are 38 flights per week flying from Colorado Springs to Chicago. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

What airlines fly to Chicago?

Frontier, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Colorado Springs according to our data. Frontier is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Colorado Springs to Chicago on average per day?

As of September 2025, 5 flights take off from Colorado Springs and land in Chicago each day. The most common flight departure time for this route is 12:00PM, with 67% of daily flights taking off in the afternoon.

What is the cheapest airline that flies from Colorado Springs to Chicago?

Southwest, United Airlines, and Delta are the most popular carriers operating from Colorado Springs to Chicago

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?

As of September 2025, there are 3 operators available to choose from 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.

$79 Cheap Flights from Colorado Springs to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Colorado Springs and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $293 to $347. The lowest price recently found on this route was $157.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Colorado Springs to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:20 am - 11:45 amCOS-MDW

2h 25mnonstop

4:00 pm - 5:35 pmMDW-COS

2h 35mnonstop

$157Southwest

Find Deal

Sat, Oct 25 - Wed, Oct 29

6:15 am - 1:35 pmCOS-MDW

6h 20m1 stop

5:00 am - 11:15 amMDW-COS

7h 15m1 stop

$177Southwest

Find Deal

Tue, Oct 28 - Tue, Nov 4

6:20 pm - 11:59 pmCOS-ORD

4h 39m1 stop

7:51 pm - 9:41 pmORD-COS

2h 50mnonstop

$189United Airlines

Find Deal

Fri, Oct 17 - Tue, Oct 21

12:36 pm - 4:21 pmCOS-ORD

2h 45mnonstop

10:04 am - 12:06 pmORD-COS

3h 02mnonstop

$192American Airlines

Find Deal

Thu, Dec 4 - Wed, Dec 10

12:32 pm - 6:55 pmCOS-ORD

5h 23m1 stop

9:20 am - 11:26 amORD-COS

3h 06mnonstop

$206United Airlines

Find Deal

Thu, Dec 11 - Wed, Dec 17

12:36 pm - 4:21 pmCOS-ORD

2h 45mnonstop

10:04 am - 12:06 pmORD-COS

3h 02mnonstop

$214American Airlines

Find Deal

Fri, Dec 12 - Wed, Dec 17

6:00 am - 2:58 pmCOS-ORD

7h 58m1 stop

5:20 am - 12:11 pmORD-COS

7h 51m1 stop

$217Delta

Find Deal

Sat, Oct 25 - Wed, Oct 29

6:00 am - 3:26 pmCOS-MDW

8h 26m1 stop

9:20 am - 10:10 pmMDW-COS

13h 50m2 stops

$222Delta

Find Deal

Sat, Oct 25 - Wed, Oct 29

10:00 am - 10:17 amCOS-ORD

23h 17m1 stop

1:03 pm - 5:14 pmORD-COS

29h 11m2 stops

$271Multiple Airlines

Find Deal

Fri, Oct 3 - Sun, Oct 5

9:11 am - 10:18 amCOS-ORD

24h 07m1 stop

6:10 am - 9:10 amORD-COS

28h 00m2 stops

$299Multiple Airlines

Find Deal

Mon, Sep 29 - Thu, Oct 2

American Airlines flights from Colorado Springs to Chicago

Our best American Airlines deals on Colorado Springs to Chicago flight tickets

American Airlines

Dec 4

COS12:36 pmColorado Springs

2h 45m

ORD4:21 pmChicago O'Hare Intl

Dec 10

ORD10:04 amChicago O'Hare Intl

3h 02m

COS12:06 pmColorado Springs

$192

Find similar

American Airlines

Dec 12

COS12:36 pmColorado Springs

2h 45m

ORD4:21 pmChicago O'Hare Intl

Dec 17

ORD10:04 amChicago O'Hare Intl

3h 02m

COS12:06 pmColorado Springs

$214

Find similar

American Airlines

Dec 5

COS12:36 pmColorado Springs

2h 45m

ORD4:21 pmChicago O'Hare Intl

Dec 8

ORD10:04 amChicago O'Hare Intl

3h 02m

COS12:06 pmColorado Springs

$225

Find similar

United Airlines flights from Colorado Springs to Chicago

Our best United Airlines deals on Colorado Springs to Chicago flight tickets

United Airlines

Oct 17

COS6:20 pmColorado Springs

4h 39m

1 stop

ORD11:59 pmChicago O'Hare Intl

Oct 21

ORD7:51 pmChicago O'Hare Intl

2h 50m

COS9:41 pmColorado Springs

$189

Find similar

United Airlines

Dec 11

COS12:32 pmColorado Springs

5h 23m

1 stop

ORD6:55 pmChicago O'Hare Intl

Dec 17

ORD9:20 amChicago O'Hare Intl

3h 06m

COS11:26 amColorado Springs

$206

Find similar

United Airlines

Oct 8

COS6:00 amColorado Springs

2h 41m

ORD9:41 amChicago O'Hare Intl

Oct 10

ORD1:00 pmChicago O'Hare Intl

5h 32m

1 stop

COS5:32 pmColorado Springs

$207

Find similar

momondo Fare Finder

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 - MDW

COSMDW

Colorado Springs

Sat 10/25

8:20 am-11:45 am

Nonstop2h 25m

Chicago Midway

Wed 10/29

4:00 pm-5:35 pm

Nonstop2h 35m

$157

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 10/28

6:15 am-1:35 pm

1 stop6h 20m

Chicago Midway

Tue 11/4

5:00 am-11:15 am

1 stop7h 15m

$177

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Fri 10/17

6:20 pm-11:59 pm

1 stop4h 39m

Chicago O'Hare Intl

Tue 10/21

7:51 pm-9:41 pm

Nonstop2h 50m

$189

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Thu 12/4

12:36 pm-4:21 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 12/10

10:04 am-12:06 pm

Nonstop3h 02m

$192

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Thu 12/11

12:32 pm-6:55 pm

1 stop5h 23m

Chicago O'Hare Intl

Wed 12/17

9:20 am-11:26 am

Nonstop3h 06m

$206

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Fri 12/12

12:36 pm-4:21 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 12/17

10:04 am-12:06 pm

Nonstop3h 02m

$214

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sat 10/25

6:00 am-2:58 pm

1 stop7h 58m

Chicago O'Hare Intl

Wed 10/29

5:20 am-12:11 pm

1 stop7h 51m

$217

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 10/25

6:00 am-3:26 pm

1 stop8h 26m

Chicago Midway

Wed 10/29

9:20 am-10:10 pm

2 stops13h 50m

$222

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Fri 10/3

10:00 am-10:17 am

1 stop23h 17m

Chicago O'Hare Intl

Sun 10/5

1:03 pm-5:14 pm

2 stops29h 11m

$271

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Mon 9/29

9:11 am-10:18 am

1 stop24h 07m

Chicago O'Hare Intl

Thu 10/2

6:10 am-9:10 am

2 stops28h 00m

$299

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Colorado Springs and Chicago?

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 Friday when prices can be found for as low as $297. 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 $505.

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 $193. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $622.

What is the cheapest Colorado Springs to Chicago flight route?

Fly from Colorado Springs to Chicago O'Hare Intl 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?

No. A direct flight is the cheapest option for a flight between Colorado Springs to Chicago.

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

As of September 2025, prices for Colorado Springs to Chicago flights are approximately 24% 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	$192
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 $192. The best round-trip flight deal from Colorado Springs to Chicago found on momondo in the last 72 hours is $304.

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)

Search flight deals

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?
As of September 2025, there are 3 operators available to choose from 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?
momondo data reveals that the most frequently booked plane model on the route from Colorado Springs to Chicago is Embraer 175 (Enhanced Winglets), representing 23.68% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet 700 at 23.39%, Boeing 737-900 at 10.82%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 10.23%.
What is the most popular airline from Colorado Springs to Chicago?
momondo data reveals that the most frequently booked airline on the route from Colorado Springs to Chicago is Southwest, representing 51% of all bookings. The subsequent popular airlines are United Airlines at 39% and American Airlines at 9%.

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 Airlines	PriceFrom $223	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $233	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
United Airlines	PriceFrom $290	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights

Southwest Flights From Colorado Springs to Chicago
Across 5 Southwest flights from Colorado Springs to Chicago this week, the average price was $337, with the best Southwest deals starting from $233 round-trip. 4,242 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 8,926 reviews) operates around 14 flights from Colorado Springs to Chicago in any given week. The average United Airlines airfare for this route is around $401, 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.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Fri 10/17

Fri 10/24

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Cheap flights from Colorado Springs to Chicago from $79

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 10/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Colorado Springs to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

American Airlines flights from Colorado Springs to Chicago

Our best American Airlines deals on Colorado Springs to Chicago flight tickets

United Airlines flights from Colorado Springs to Chicago

Our best United Airlines deals on Colorado Springs to Chicago flight tickets

momondo Fare Finder

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

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 typical price of a round-trip flight between Colorado Springs and Chicago?

What is the cheapest month to fly to Chicago?

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

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 $193. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $622.

What is the cheapest Colorado Springs to Chicago flight route?

Fly from Colorado Springs to Chicago O'Hare Intl 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?

No. A direct flight is the cheapest option for a flight between Colorado Springs to Chicago.

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

As of September 2025, prices for Colorado Springs to Chicago flights are approximately 24% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Colorado Springs to Chicago?

Southwest, United Airlines, and Delta are the most popular carriers operating from Colorado Springs to Chicago

What airlines fly to Chicago?

How many flights depart from Colorado Springs to Chicago on average per day?

As of September 2025, 5 flights take off from Colorado Springs and land in Chicago each day. The most common flight departure time for this route is 12:00PM, with 67% of daily flights taking off in the afternoon.

How many flights depart from Colorado Springs to Chicago on average per week?

As of September 2025, there are 38 flights per week flying from Colorado Springs to Chicago. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

When to book flights from Colorado Springs to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Colorado Springs to Chicago by plane?

When did momondo last update prices for flights from Colorado Springs Airport to Chicago?

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?

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

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

Southwest Flights From Colorado Springs to Chicago

United Airlines Flights From Colorado Springs to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights 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?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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