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$114+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Colorado Springs to Chicago are usually found in February or January, booked 62 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 May 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$237
(United Airlines)

One-way from

$114
(Southwest)

Popular in

October

Cheapest in

February

Average price

$330

Good round-trip deal

$348 or less

Good one-way deal

$138 or less
Provider with most accurate pricing for Colorado Springs-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Colorado Springs-Chicago (CHI) flights.
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From Colorado Springs to Chicago (CHI)
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One-way flight from Colorado Springs to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Colorado Springs to Chicago (CHI).
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Price to beat on a one-way flight from Colorado Springs to Chicago (CHI).
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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 May 1, 2025.

This United Airlines deal was found by Cheapflights users on 4/30. 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 5/286:30 pmCOS - ORD
1 stop4h 55mUnited Airlines
Wed 6/49:15 amORD - COS
Nonstop2h 53mUnited Airlines
Deal found 4/30$237
This Delta deal was found by Cheapflights users on 4/29. 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 7/158:15 amCOS - ORD
1 stop9h 10mDelta
Tue 7/227:00 amORD - COS
1 stop7h 27mDelta
Deal found 4/29$247
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Sat 6/76:01 amCOS - ORD
1 stop5h 24mAmerican Airlines
Tue 6/109:42 amORD - COS
Nonstop2h 49mAmerican Airlines
Deal found 4/29$250
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 8/96:00 amCOS - MDW
1 stop8h 27mDelta
Wed 8/206:00 amMDW - COS
1 stop7h 50mDelta
Deal found 4/29$259
This Southwest deal was found by Cheapflights users on 4/29. 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.
Fri 7/253:50 pmCOS - MDW
Nonstop2h 25mSouthwest
Tue 7/296:55 amMDW - COS
1 stop6h 00mSouthwest
Deal found 4/29$272
This Southwest deal was found by Cheapflights users on 4/30. 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.
Thu 9/1811:45 amCOS - ORD
1 stop9h 35mSouthwest
Wed 9/247:00 amORD - COS
1 stop4h 40mSouthwest
Deal found 4/30$278
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Fri 6/65:45 pmCOS - ORD
3 stops34h 40mMultiple Airlines
Sun 6/811:50 amORD - COS
2 stops30h 10mMultiple Airlines
Deal found 4/30$318

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 May 1, 2025.
Use the filters below to find and compare flights from Colorado Springs to Chicago that are best for you.

Fly from

Colorado Springs

Fly to

Chicago

Route

Depart

Return

Price

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 5/28

6:30 pm-12:25 am

1 stop4h 55m

Chicago O'Hare Intl

Wed 6/4

9:15 am-11:08 am

Nonstop2h 53m

$237

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 7/15

8:15 am-6:25 pm

1 stop9h 10m

Chicago O'Hare Intl

Tue 7/22

7:00 am-1:27 pm

1 stop7h 27m

$247

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sat 6/7

6:01 am-12:25 pm

1 stop5h 24m

Chicago O'Hare Intl

Tue 6/10

9:42 am-11:31 am

Nonstop2h 49m

$250

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 8/9

6:00 am-3:27 pm

1 stop8h 27m

Chicago Midway

Wed 8/20

6:00 am-12:50 pm

1 stop7h 50m

$259

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 7/25

3:50 pm-7:15 pm

Nonstop2h 25m

Chicago Midway

Tue 7/29

6:55 am-11:55 am

1 stop6h 00m

$272

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Thu 9/18

11:45 am-11:40 pm

2 stops10h 55m

Chicago O'Hare Intl

Wed 9/24

7:00 am-10:40 am

1 stop4h 40m

$278

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Fri 6/6

5:45 pm-5:25 am

3 stops34h 40m

Chicago O'Hare Intl

Sun 6/8

11:50 am-5:00 pm

2 stops30h 10m

$318

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 7/1

2:55 pm-6:15 pm

Nonstop2h 20m

$114

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Tue 7/1

12:05 pm-3:45 pm

Nonstop2h 40m

$114

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 7/1

10:57 am-5:40 pm

1 stop5h 43m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 13 results
1
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Colorado Springs-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 April 25, 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 62 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 May 1, 2025.

A simple way to save on the total cost of your ticket is to fly from Colorado Springs to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 9% on your trip compared to booking a flight in the morning.

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 May 1, 2025.

The most flights from COS to CHI are scheduled on a Wednesday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

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 May 1, 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
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 5 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 United Airlines. Our recent data shows that you can find tickets from as low as $237 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $247 and $250 round-trip. Users have found that United Airlines is 35% 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 ($114), United Airlines ($114), and Delta ($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: Emirates (90%), Lufthansa (87%), SkyWest Airlines( 86%).

  • 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 $227 on average our data indicates $625 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Colorado Springs to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$217Average$475FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$265Average$338FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$268Average$397FlexibilityNo cancel feeOn-time69%

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