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$111+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
1 adult, Economy
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Cheapflights Tip: The best prices from Colorado Springs to Chicago are usually found in January or October, booked 79 days in advance, depart on a Wednesday or Friday and return on a Saturday

Cheap 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 March 22, 2026.

This United Airlines deal was found by Cheapflights users on 3/17. 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.
Sat 5/211:43 am
COS
-
ORD
Nonstop2h 44m
United Airlines
Tue 5/58:46 am
ORD
-
COS
Nonstop3h 01m
United Airlines
Deal found 3/17$211
This Delta deal was found by Cheapflights users on 3/19. 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.
Tue 4/141:14 pm
COS
-
MDW
1 stop8h 14m
Delta
Wed 4/156:00 am
MDW
-
COS
1 stop7h 17m
Delta
Deal found 3/19$221
This Southwest deal was found by Cheapflights users on 3/17. 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 5/22:15 pm
COS
-
ORD
1 stop8h 10m
Southwest
Tue 5/510:30 am
ORD
-
COS
1 stop6h 00m
Southwest
Deal found 3/17$231
This Southwest deal was found by Cheapflights users on 3/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:20 am
COS
-
MDW
1 stop7h 45m
Southwest
Mon 4/205:30 am
MDW
-
COS
1 stop5h 30m
Southwest
Deal found 3/19$241
This Southwest deal was found by Cheapflights users on 3/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:15 am
COS
-
ORD
1 stop6h 15m
Southwest
Mon 4/204:50 pm
ORD
-
COS
1 stop8h 00m
Southwest
Deal found 3/19$241
This Southwest deal was found by Cheapflights users on 3/18. 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 5/26:20 am
COS
-
MDW
1 stop10h 30m
Southwest
Sat 5/95:10 am
MDW
-
COS
1 stop8h 25m
Southwest
Deal found 3/18$246
This Delta deal was found by Cheapflights users on 3/17. 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.
Thu 4/96:20 am
COS
-
ORD
2 stops12h 57m
Delta
Tue 4/142:09 pm
ORD
-
COS
1 stop9h 04m
Delta
Deal found 3/17$246
This United Airlines deal was found by Cheapflights users on 3/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:33 pm
COS
-
ORD
1 stop4h 26m
United Airlines
Mon 4/207:45 pm
ORD
-
COS
Nonstop3h 09m
United Airlines
Deal found 3/19$250
This United Airlines deal was found by Cheapflights users on 3/20. 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.
Sat 4/116:00 am
COS
-
ORD
Nonstop2h 50m
United Airlines
Sat 4/112:00 pm
ORD
-
COS
1 stop7h 46m
United Airlines
Deal found 3/20$252
This American Airlines deal was found by Cheapflights users on 3/17. 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.
Thu 4/91:39 pm
COS
-
ORD
1 stop8h 06m
American Airlines
Tue 4/149:53 am
ORD
-
COS
Nonstop2h 59m
American Airlines
Deal found 3/17$256
This Southwest deal was found by Cheapflights users on 3/18. 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.
Mon 5/411:30 am
COS
-
ORD
1 stop11h 25m
Southwest
Thu 5/78:00 am
ORD
-
COS
2 stops15h 15m
Southwest
Deal found 3/18$257
This American Airlines deal was found by Cheapflights users on 3/18. 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.
Mon 5/41:39 pm
COS
-
ORD
1 stop8h 06m
American Airlines
Thu 5/79:53 am
ORD
-
COS
Nonstop2h 59m
American Airlines
Deal found 3/18$266

Find 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 March 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$211
(United Airlines)

One-way from

$111
(Delta)

Popular in

November

Cheapest in

January

Average price

$339

Good round-trip deal

$323 or less

Good one-way deal

$181 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. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated March 22, 2026.
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

Cheapest round-trip

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Thu 4/9

6:20 am-8:17 pm

2 stops12h 57m

Chicago O'Hare Intl

Tue 4/14

11:00 am-8:20 pm

2 stops10h 20m

$251

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 5/19

5:12 pm-10:58 pm

1 stop4h 46m

Chicago O'Hare Intl

Wed 5/27

9:06 am-11:10 am

Nonstop3h 04m

$281
Quickest round-trip

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sat 5/2

11:43 am-3:27 pm

Nonstop2h 44m

Chicago O'Hare Intl

Tue 5/5

8:46 am-10:47 am

Nonstop3h 01m

$281

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/9

6:20 am-5:54 pm

2 stops10h 34m

Chicago Midway

Tue 4/14

12:52 pm-8:20 pm

1 stop8h 28m

$285

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sun 4/12

6:00 pm-12:50 am

1 stop5h 50m

Chicago Midway

Wed 4/15

4:00 pm-8:15 pm

1 stop5h 15m

$306

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sun 4/12

6:20 am-3:00 pm

1 stop7h 40m

Chicago O'Hare Intl

Wed 4/15

11:55 am-8:15 pm

1 stop9h 20m

$317

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Mon 4/20

5:20 pm-11:40 pm

1 stop5h 20m

Chicago Midway

Sun 4/26

6:00 am-9:20 am

1 stop4h 20m

$326

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 6/3

12:16 pm-4:02 pm

Nonstop2h 46m

Chicago O'Hare Intl

Thu 6/4

9:06 am-11:10 am

Nonstop3h 04m

$326

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sun 4/12

6:00 am-9:50 am

Nonstop2h 50m

Chicago O'Hare Intl

Wed 4/15

8:50 am-10:57 am

Nonstop3h 07m

$330

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 5/20

1:55 pm-9:09 pm

1 stop6h 14m

Chicago Midway

Fri 5/29

6:23 am-12:48 pm

1 stop7h 25m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 39 resultsSorted by cheapest first
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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 March.
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.

Cheapflights Insights

Everything you need to know about your flight from Colorado Springs to Chicago

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 March 13, 2026.

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 78 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, April is the cheapest month in which you can book a flight from Colorado Springs to Chicago (average of $81). Flying from Colorado Springs to Chicago in June is currently the most expensive (average of $140). 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 March 22, 2026.

When flying from Colorado Springs to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Colorado Springs to Chicago

Explore weekly flight availability from Colorado Springs to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 22, 2026.

The most flights from COS to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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 March 22, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Colorado Springs to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,325 reviews
Southwest
8.0
Very good
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,455 reviews
Southwest
8.0
Very good
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,489 reviews
Southwest
8.0
Very good
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 3 outbound flights to Chicago per day. 3 airlines have flights to Chicago from Colorado Springs on a regular basis.

  • How long is the flight from Colorado Springs to Chicago?

    Airlines like Delta, United Airlines, and Southwest fly from Colorado Springs to Chicago in about 4h 46m. The time it takes to get you to your destination can typically vary by up to 8h 11m. The distance from Colorado Springs to Chicago is about 908 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Our cheapest airline available from Colorado Springs to Chicago is Southwest. Our recent data shows that you can find tickets from as low as $227 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $229 and $229 round-trip. Users have found that Southwest is 32% 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 American Airlines ($93), United Airlines ($122), and Southwest ($124).

  • 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 (81%), Emirates (76%), United Airlines( 75%).

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

    Looking at all options, your cheapest flight can be booked for $140. While the most popular route (Colorado Springs - Chicago O'Hare Intl) can be booked for $241 on average, our data indicates $950 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, April is the cheapest month in which you can book a flight from Colorado Springs to Chicago (average of $81). Flying from Colorado Springs to Chicago in June is currently the most expensive (average of $140). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 March 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$227Average$357FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$229Average$382FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$354FlexibilityNo cancel feeOn-time71%

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