Which layover airport has the shortest travel time from Colorado Springs to Chicago?

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 4h 34m.

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

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

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

As of August 2025, there are 29 flights per week flying from Colorado Springs to Chicago. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

Which layover airport offers the lowest fares from Colorado Springs to Chicago?

Flights via Denver (DEN) offer the lowest average round-trip price of $294.

Which layover airport has the shortest connection time from Colorado Springs to Chicago?

Denver (DEN) has the shortest average layover time for this route: 0h 57m.

Which airport is the most popular layover for flights between Colorado Springs and Chicago?

Atlanta (ATL) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

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

As of August 2025, 4 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 airlines fly to Chicago?

Frontier, United Airlines and Southwest 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 32% 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.

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 August 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.

$115 Cheap Flights from Colorado Springs to Chicago (COS-CHI) in 2025

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Find the cheapest flights from Colorado Springs to Chicago (COS-CHI)

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

9:31 am - 10:17 amCOS-ORD

23h 46m1 stop

8:05 am - 8:21 amORD-COS

25h 16m1 stop

$233

Find Deal

Fri, Sep 19 - Sun, Sep 28

1:55 pm - 5:15 pmCOS-MDW

2h 20mnonstop

6:00 pm - 7:35 pmMDW-COS

2h 35mnonstop

$240Southwest

Find Deal

Wed, Oct 15 - Sat, Oct 18

12:05 pm - 3:49 pmCOS-ORD

2h 44mnonstop

9:40 am - 11:34 amORD-COS

2h 54mnonstop

$240American Airlines

Find Deal

Wed, Oct 22 - Sat, Oct 25

12:40 pm - 4:26 pmCOS-ORD

2h 46mnonstop

10:06 am - 12:10 pmORD-COS

3h 04mnonstop

$243American Airlines

Find Deal

Sat, Nov 8 - Sat, Nov 15

6:00 am - 9:52 amCOS-ORD

2h 52mnonstop

12:55 pm - 5:30 pmORD-COS

5h 35m1 stop

$250United Airlines

Find Deal

Sat, Sep 20 - Tue, Sep 23

1:55 pm - 5:15 pmCOS-MDW

2h 20mnonstop

5:15 am - 10:15 amMDW-COS

6h 00m1 stop

$250Southwest

Find Deal

Wed, Oct 15 - Sat, Oct 18

12:05 pm - 3:49 pmCOS-ORD

2h 44mnonstop

5:17 pm - 10:09 pmORD-COS

5h 52m1 stop

$254American Airlines

Find Deal

Wed, Oct 22 - Sat, Oct 25

3:40 pm - 9:32 pmCOS-ORD

4h 52m1 stop

12:55 pm - 4:34 pmORD-COS

4h 39m1 stop

$260United Airlines

Find Deal

Sat, Sep 20 - Tue, Sep 23

5:55 pm - 8:40 amCOS-ORD

13h 45m2 stops

10:35 am - 8:39 pmORD-COS

11h 04m2 stops

$270Delta

Find Deal

Tue, Sep 23 - Sat, Sep 27

11:11 am - 5:37 pmCOS-MDW

5h 26m1 stop

6:00 am - 12:12 pmMDW-COS

7h 12m1 stop

$298Delta

Find Deal

Sat, Aug 30 - Wed, Sep 3

Delta flights from Colorado Springs to Chicago

Our best Delta deals on Colorado Springs to Chicago flight tickets

Delta

Sep 23

COS5:55 pmColorado Springs

13h 45m

2 stops

ORD8:40 amChicago O'Hare Intl

Sep 27

ORD10:35 amChicago O'Hare Intl

11h 04m

2 stops

COS8:39 pmColorado Springs

$270

Find similar

Delta

Aug 30

COS11:11 amColorado Springs

5h 26m

1 stop

MDW5:37 pmChicago Midway

Sep 3

MDW6:00 amChicago Midway

7h 12m

1 stop

COS12:12 pmColorado Springs

$298

Find similar

Delta

Nov 7

COS5:49 pmColorado Springs

13h 40m

2 stops

ORD8:29 amChicago O'Hare Intl

Nov 10

ORD6:00 amChicago O'Hare Intl

7h 57m

1 stop

COS12:57 pmColorado Springs

$302

Find similar

Southwest flights from Colorado Springs to Chicago

Our best Southwest deals on Colorado Springs to Chicago flight tickets

Southwest

Oct 15

COS1:55 pmColorado Springs

2h 20m

MDW5:15 pmChicago Midway

Oct 18

MDW6:00 pmChicago Midway

2h 35m

COS7:35 pmColorado Springs

$240

Find similar

Southwest

Oct 15

COS1:55 pmColorado Springs

2h 20m

MDW5:15 pmChicago Midway

Oct 18

MDW5:15 amChicago Midway

6h 00m

1 stop

COS10:15 amColorado Springs

$250

Find similar

Southwest

Nov 8

COS5:00 amColorado Springs

7h 00m

1 stop

ORD1:00 pmChicago O'Hare Intl

Nov 15

ORD1:00 pmChicago O'Hare Intl

8h 00m

1 stop

COS8:00 pmColorado Springs

$263

Find similar

Fly from

Fly to

Route

Depart

Return

Price

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Fri 9/19

9:31 am-10:17 am

1 stop23h 46m

Chicago O'Hare Intl

Sun 9/28

8:05 am-8:21 am

1 stop25h 16m

$233

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/15

1:55 pm-5:15 pm

Nonstop2h 20m

Chicago Midway

Sat 10/18

6:00 pm-7:35 pm

Nonstop2h 35m

$240

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 10/22

12:05 pm-3:49 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 10/25

9:40 am-11:34 am

Nonstop2h 54m

$240

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sat 11/8

12:40 pm-4:26 pm

Nonstop2h 46m

Chicago O'Hare Intl

Sat 11/15

10:06 am-12:10 pm

Nonstop3h 04m

$243

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sat 9/20

6:00 am-9:52 am

Nonstop2h 52m

Chicago O'Hare Intl

Tue 9/23

12:55 pm-5:30 pm

1 stop5h 35m

$250

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/15

1:55 pm-5:15 pm

Nonstop2h 20m

Chicago Midway

Sat 10/18

5:15 am-10:15 am

1 stop6h 00m

$250

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 10/22

12:05 pm-3:49 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 10/25

5:17 pm-10:09 pm

1 stop5h 52m

$254

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sat 9/20

3:40 pm-9:32 pm

1 stop4h 52m

Chicago O'Hare Intl

Tue 9/23

12:55 pm-4:34 pm

1 stop4h 39m

$260

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 9/23

5:55 pm-8:40 am

2 stops13h 45m

Chicago O'Hare Intl

Sat 9/27

10:35 am-8:39 pm

2 stops11h 04m

$270

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 8/30

11:11 am-5:37 pm

1 stop5h 26m

Chicago Midway

Wed 9/3

6:00 am-12:12 pm

1 stop7h 12m

$298

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

Layovers

Other information

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 $312.

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 $295. 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 $500.

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 $191. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $634.

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Colorado Springs when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $393 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Colorado Springs for as low as $155 on momondo.

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 August 2025, prices for Colorado Springs to Chicago flights are approximately 54% 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	$115
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 $115. The best round-trip flight deal from Colorado Springs to Chicago found on momondo in the last 72 hours is $233.

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 August 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 25.64% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet 700 at 22.56%, Boeing 737-700 at 17.69%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 11.54%.
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 50% of all bookings. The subsequent popular airlines are United Airlines at 41% 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 $217	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $265	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
United Airlines	PriceFrom $286	Free Cancellation	Rating 7.4 8,925 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 $332, with the best Southwest deals starting from $265 round-trip. 4,246 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 8,925 reviews) operates around 8 flights from Colorado Springs to Chicago in any given week. The average United Airlines airfare for this route is around $402, with deals from around $286 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.

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Cheap flights from Colorado Springs to Chicago from $115

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 11/10. 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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Delta flights from Colorado Springs to Chicago

Our best Delta deals on Colorado Springs to Chicago flight tickets

Southwest flights from Colorado Springs to Chicago

Our best Southwest deals on Colorado Springs to Chicago flight tickets

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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?

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 $191. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $634.

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

How far in advance should I book a flight to Chicago?

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 August 2025, prices for Colorado Springs to Chicago flights are approximately 54% 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 American Airlines are the most popular carriers operating from Colorado Springs to Chicago

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Colorado Springs and Chicago?

Atlanta (ATL) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Colorado Springs to Chicago?

Flights via Denver (DEN) offer the lowest average round-trip price of $294.

Which layover airport has the shortest travel time from Colorado Springs to Chicago?

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 4h 34m.

Which layover airport has the shortest connection time from Colorado Springs to Chicago?

Denver (DEN) has the shortest average layover time for this route: 0h 57m.

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

As of August 2025, 4 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 August 2025, there are 29 flights per week flying from Colorado Springs to Chicago. The most common day of the week flights depart is Mon, with 21% 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.