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$79+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Colorado Springs to Chicago are usually found in February or August, booked 79 days in advance, depart on a Wednesday or Thursday 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 September 15, 2025.

Round-trip from

$165
(United Airlines)

One-way from

$79
(Southwest)

Popular in

November

Cheapest in

February

Average price

$338

Good round-trip deal

$304 or less

Good one-way deal

$192 or less
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. 16% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/12. 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 10/113:40 pmCOS - ORD
1 stop4h 50mUnited Airlines
Sat 10/189:10 amORD - COS
Nonstop3h 05mUnited Airlines
Deal found 9/12$165
This Southwest deal was found by Cheapflights users on 9/14. 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 10/295:30 pmCOS - MDW
1 stop4h 10mSouthwest
Sat 11/16:00 pmMDW - COS
Nonstop2h 35mSouthwest
Deal found 9/14$167
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2911:35 amCOS - ORD
1 stop4h 10mSouthwest
Sat 11/17:00 amORD - COS
1 stop4h 15mSouthwest
Deal found 9/14$177
This American Airlines deal was found by Cheapflights users on 9/13. 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 11/812:40 pmCOS - ORD
Nonstop2h 46mAmerican Airlines
Tue 11/1110:02 amORD - COS
Nonstop3h 04mAmerican Airlines
Deal found 9/13$192
This Southwest deal was found by Cheapflights users on 9/15. 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 12/56:35 amCOS - MDW
1 stop7h 25mSouthwest
Mon 12/85:00 amMDW - COS
1 stop7h 15mSouthwest
Deal found 9/15$199
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/296:20 pmCOS - ORD
1 stop4h 39mUnited Airlines
Tue 11/49:20 amORD - COS
Nonstop3h 06mUnited Airlines
Deal found 9/14$211
This Southwest deal was found by Cheapflights users on 9/14. 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 10/2911:35 amCOS - ORD
1 stop4h 10mSouthwest
Tue 11/42:15 pmORD - COS
1 stop6h 10mSouthwest
Deal found 9/14$212
This Delta deal was found by Cheapflights users on 9/13. 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 11/88:09 amCOS - MDW
2 stops8h 34mDelta
Tue 11/1112:47 pmMDW - COS
1 stop8h 53mDelta
Deal found 9/13$222
This Southwest deal was found by Cheapflights users on 9/12. 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 10/318:15 amCOS - MDW
Nonstop2h 25mSouthwest
Sun 11/25:00 amMDW - COS
1 stop5h 50mSouthwest
Deal found 9/12$223
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/512:36 pmCOS - ORD
Nonstop2h 45mAmerican Airlines
Mon 12/810:04 amORD - COS
Nonstop3h 02mAmerican Airlines
Deal found 9/15$225
This Southwest deal was found by Cheapflights users on 9/13. 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 11/86:25 amCOS - MDW
1 stop12h 45mSouthwest
Tue 11/112:35 pmMDW - COS
1 stop7h 55mSouthwest
Deal found 9/13$245
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sun 10/2611:45 amCOS - MDW
Nonstop2h 25mSouthwest
Thu 10/305:50 amMDW - COS
1 stop7h 00mSouthwest
Deal found 9/13$254

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 September 15, 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

Sat 10/11

3:40 pm-9:30 pm

1 stop4h 50m

Chicago O'Hare Intl

Sat 10/18

9:10 am-11:15 am

Nonstop3h 05m

$165

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/29

5:30 pm-10:40 pm

1 stop4h 10m

Chicago Midway

Sat 11/1

6:00 pm-7:35 pm

Nonstop2h 35m

$167

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 10/29

11:35 am-4:45 pm

1 stop4h 10m

Chicago O'Hare Intl

Sat 11/1

7:00 am-10:15 am

1 stop4h 15m

$177

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 12/5

6:35 am-3:00 pm

1 stop7h 25m

Chicago Midway

Mon 12/8

5:00 am-11:15 am

1 stop7h 15m

$199

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 10/29

11:35 am-9:30 pm

2 stops8h 55m

Chicago O'Hare Intl

Tue 11/4

2:15 pm-9:30 pm

2 stops8h 15m

$222

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Fri 12/5

12:36 pm-4:21 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 12/8

10:04 am-12:06 pm

Nonstop3h 02m

$225

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Wed 10/29

6:20 pm-11:59 pm

1 stop4h 39m

Chicago O'Hare Intl

Sat 11/1

9:20 am-11:26 am

Nonstop3h 06m

$241

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 11/8

6:25 am-8:10 pm

1 stop12h 45m

Chicago Midway

Tue 11/11

2:35 pm-9:30 pm

1 stop7h 55m

$245

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Fri 10/10

12:00 pm-3:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Wed 10/15

5:01 am-9:05 am

1 stop5h 04m

$251

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sun 10/26

11:45 am-3:10 pm

Nonstop2h 25m

Chicago Midway

Thu 10/30

5:50 am-11:50 am

1 stop7h 00m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 35 results
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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 September 12, 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 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, 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 September 15, 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 6% 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 September 15, 2025.

The most flights from COS to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Colorado Springs to Chicago?

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 September 15, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

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

    Airlines like United Airlines, Southwest, and American Airlines fly from Colorado Springs to Chicago in about 2h 45m. The time it takes to get you to your destination can typically vary by up to 2h 05m. 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 American Airlines. Our recent data shows that you can find tickets from as low as $223 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $233 and $290 round-trip. Users have found that American Airlines is 37% cheaper than the other options available to this destination.

  • 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: United Airlines (87%), Emirates (75%), SkyWest Airlines( 72%).

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

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (Colorado Springs - Chicago O'Hare Intl) can be booked for $177 on average, our data indicates $554 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$223Average$373FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$233Average$337FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$290Average$401FlexibilityNo cancel feeOn-time69%

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