HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$128+ Cheap flights from Colorado Springs (COS) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Colorado Springs to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Colorado Springs to Chicago are usually found in February or January, booked 24 days in advance, depart on a Wednesday or Thursday and return on a Monday

Cheap flight deals from Colorado Springs to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Colorado Springs (COS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$275
(Delta)

One-way from

$128
(Southwest)

Popular in

October

Cheapest in

February

Average price

$309

Good round-trip deal

$346 or less

Good one-way deal

$158 or less
Provider with most accurate pricing for Colorado Springs-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Colorado Springs-Chicago (CHI) flights.
Search Deals
From Colorado Springs to Chicago (CHI)
Search Deals
One-way flight from Colorado Springs to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
Price to beat on a round-trip flight from Colorado Springs to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Colorado Springs to Chicago (CHI).
Search Deals

Find flight deals from Colorado Springs to Chicago

Cheapest flights from Colorado Springs to Chicago
Explore the most affordable flight options available from Colorado Springs to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/28:15 amCOS - ORD
1 stop8h 31mDelta
Wed 4/91:45 pmORD - COS
1 stop6h 20mDelta
Deal found 2/20$275
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/261:10 pmCOS - MDW
Nonstop2h 20mSouthwest
Fri 3/2810:05 amMDW - COS
Nonstop2h 40mSouthwest
Deal found 2/20$283
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/27:30 amCOS - ORD
1 stop6h 25mUnited Airlines
Wed 4/99:30 amORD - COS
Nonstop3h 05mUnited Airlines
Deal found 2/20$284
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/122:45 pmCOS - ORD
1 stop6h 15mSouthwest
Mon 4/145:25 pmORD - COS
1 stop7h 10mSouthwest
Deal found 2/20$295
This American Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/612:13 pmCOS - ORD
Nonstop2h 44mAmerican Airlines
Fri 6/209:45 amORD - COS
Nonstop2h 45mAmerican Airlines
Deal found 2/19$311
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/306:24 pmCOS - ORD
3 stops39h 45mMultiple Airlines
Wed 4/22:34 pmORD - COS
2 stops28h 02mMultiple Airlines
Deal found 2/20$361
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/26:00 amCOS - MDW
2 stops11h 02mDelta
Wed 4/99:52 amMDW - COS
1 stop9h 01mDelta
Deal found 2/19$372

Find flights from Colorado Springs to Chicago within your budget

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, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Colorado Springs

Fly to

Chicago

Route

Depart

Return

Price

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 4/2

8:15 am-5:46 pm

1 stop8h 31m

Chicago O'Hare Intl

Wed 4/9

1:45 pm-7:05 pm

1 stop6h 20m

$275

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 3/26

1:10 pm-4:30 pm

Nonstop2h 20m

Chicago Midway

Fri 3/28

10:05 am-11:45 am

Nonstop2h 40m

$283

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 4/2

7:30 am-2:55 pm

1 stop6h 25m

Chicago O'Hare Intl

Wed 4/9

9:30 am-11:35 am

Nonstop3h 05m

$284

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sat 4/12

2:45 pm-10:00 pm

1 stop6h 15m

Chicago O'Hare Intl

Mon 4/14

5:25 pm-11:35 pm

1 stop7h 10m

$295

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Fri 6/6

12:13 pm-3:57 pm

Nonstop2h 44m

Chicago O'Hare Intl

Fri 6/20

9:45 am-11:30 am

Nonstop2h 45m

$311

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sun 3/30

6:24 pm-11:09 am

3 stops39h 45m

Chicago O'Hare Intl

Wed 4/2

2:34 pm-5:36 pm

2 stops28h 02m

$361

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 4/2

6:00 am-6:02 pm

2 stops11h 02m

Chicago Midway

Wed 4/9

9:52 am-5:53 pm

1 stop9h 01m

$372

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 4/16

1:50 pm-5:10 pm

Nonstop2h 20m

$128

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Thu 4/24

12:55 pm-4:43 pm

Nonstop2h 48m

$128

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 4/16

8:05 am-10:26 pm

2 stops13h 21m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 15 results
1
2

Compare providers for flights from Colorado Springs to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Colorado Springs to Chicago in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Colorado Springs-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Colorado Springs-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Colorado Springs-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Colorado Springs-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Colorado Springs-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Colorado Springs to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Colorado Springs with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Colorado Springs to Chicago

Get recent, data-driven insights about flights from Colorado Springs to Chicago including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Colorado Springs to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Colorado Springs to Chicago. Price data was last updated on February 14, 2025.

The price you pay for your flight from Colorado Springs to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 24 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Colorado Springs to Chicago?

Currently, August is the cheapest month in which you can book a flight from Colorado Springs to Chicago (average of $245). Flying from Colorado Springs to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from COS to CHI?

Find hourly flight availability from Colorado Springs to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Colorado Springs to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight in the morning.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 20, 2025.
See what other customers who have flown with Southwest, Delta and United Airlines from Colorado Springs to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Colorado Springs to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Colorado Springs to Chicago?

    For a flight from Colorado Springs to Chicago, you will be flying from Colorado Springs. Colorado Springs (COS) is just 6.7 mi from the center of the city. Colorado Springs is the only Colorado Springs airport and it handles 2 outbound flights to Chicago per day. 3 airlines have flights to Chicago from Colorado Springs on a regular basis.

  • What are the cheapest airlines flying from Colorado Springs to Chicago round-trip?

    Our cheapest airline available from Colorado Springs to Chicago is Delta. Our recent data shows that you can find tickets from as low as $275 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $283 and $286 round-trip. Users have found that Delta is 26% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Colorado Springs to Chicago one-way?

    The cheapest airlines for a one-way flight from Colorado Springs to Chicago are Southwest ($128), United Airlines ($128), and Delta ($143).

  • What are the most reliable airlines from Colorado Springs to Chicago?

    Before booking your flight to Chicago from Colorado Springs, check out the most reliable airlines to get you to your destination on time: Lufthansa (95%), Emirates (88%), SkyWest Airlines( 76%).

  • What are the cheapest flights from Colorado Springs to Chicago?

    Looking at all options, your cheapest flight can be booked for $127. While the most popular route (Colorado Springs - Chicago O'Hare Intl) can be booked for $280 on average our data indicates $419 when flying from Colorado Springs to Chicago.

  • Can I find deals for flights from Colorado Springs to Chicago that include hotel bookings?

    Yes. In addition to deals on Colorado Springs to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Colorado Springs to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Colorado Springs to Chicago.

  • Can I find deals for business class flights from Colorado Springs to Chicago?

    Yes. Cheapflights offers flight deals from Colorado Springs to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Colorado Springs to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Colorado Springs to Chicago (average of $245). Flying from Colorado Springs to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Colorado Springs?

Book flights to Colorado Springs if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Colorado Springs to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Denver to O'Hare Intl flights
Denver to Midway flights
Denver to St. Louis flights
Colorado Springs to O'Hare Intl flights
Denver to Moline flights
Colorado Springs to Midway flights
Montrose to O'Hare Intl flights
Colorado Springs to St. Louis flights
Grand Junction to O'Hare Intl flights
Denver to Peoria flights
Grand Junction to St. Louis flights
Durango to O'Hare Intl flights
Grand Junction to Midway flights
Vail to O'Hare Intl flights
Aspen to O'Hare Intl flights
Denver to Bloomington flights
Montrose to Midway flights
Vail to St. Louis flights
Hayden to O'Hare Intl flights
Montrose to St. Louis flights
Denver to Champaign flights
Denver to Evansville flights
Aspen to Midway flights
Gunnison to O'Hare Intl flights
Colorado Springs to Evansville flights
Denver to Rockford flights
Durango to St. Louis flights
Denver to Dubuque flights
Denver to Decatur flights
Grand Junction to Peoria flights
Gunnison to St. Louis flights
Colorado Springs to Moline flights
Denver to Springfield flights
Aspen to St. Louis flights
Vail to Midway flights
Montrose to Peoria flights
Hayden to St. Louis flights
Colorado Springs to Bloomington flights
Colorado Springs to Peoria flights
Colorado Springs to Springfield flights
Hayden to Moline flights
Colorado Springs to Champaign flights
Durango to Midway flights
Grand Junction to Bloomington flights
Durango to Moline flights
Montrose to Springfield flights

Top 3 airlines flying from Colorado Springs to Chicago

Discover the top 3 airlines that operate flights from Colorado Springs to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$254Average$397FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$260Average$475FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$291Average$384FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.