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$69+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
COS — CHI
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 81 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 agosto 14, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

November

Cheapest in

February

Average price

$312

Good round-trip deal

$264 or less

Good one-way deal

$179 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. 13% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 14, 2025.

This Southwest deal was found by Cheapflights users on 8/13. 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.
mié. 10/221:55 pmCOS - MDW
Nonstop2h 20mSouthwest
mar. 10/284:00 pmMDW - COS
Nonstop2h 35mSouthwest
Deal found 8/13$137
This Southwest deal was found by Cheapflights users on 8/14. 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.
mié. 10/221:55 pmCOS - MDW
Nonstop2h 20mSouthwest
lun. 10/2712:00 pmMDW - COS
Nonstop2h 35mSouthwest
Deal found 8/14$177
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/612:25 pmCOS - ORD
Nonstop2h 45mAmerican Airlines
mar. 9/99:56 amORD - COS
Nonstop2h 55mAmerican Airlines
Deal found 8/12$177
This Southwest deal was found by Cheapflights users on 8/14. 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.
vie. 10/32:10 pmCOS - MDW
Nonstop2h 20mSouthwest
mar. 10/74:00 pmMDW - COS
Nonstop2h 35mSouthwest
Deal found 8/14$183
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/135:10 pmCOS - ORD
1 stop5h 49mUnited Airlines
mar. 9/167:50 pmORD - COS
Nonstop3h 04mUnited Airlines
Deal found 8/13$187
This Southwest deal was found by Cheapflights users on 8/12. 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.
sáb. 10/188:20 amCOS - MDW
Nonstop2h 25mSouthwest
mar. 10/214:00 pmMDW - COS
Nonstop2h 35mSouthwest
Deal found 8/12$203
This Southwest deal was found by Cheapflights users on 8/13. 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.
mié. 9/175:05 pmCOS - ORD
1 stop5h 00mSouthwest
vie. 9/196:55 pmORD - COS
1 stop4h 40mSouthwest
Deal found 8/13$203
This American Airlines deal was found by Cheapflights users on 8/13. 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.
mié. 10/2212:05 pmCOS - ORD
Nonstop2h 44mAmerican Airlines
mar. 10/289:40 amORD - COS
Nonstop2h 54mAmerican Airlines
Deal found 8/13$207
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/196:00 amCOS - ORD
Nonstop2h 41mUnited Airlines
mié. 10/227:51 pmORD - COS
Nonstop2h 50mUnited Airlines
Deal found 8/13$209
This Southwest deal was found by Cheapflights users on 8/13. 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.
lun. 9/89:45 amCOS - MDW
Nonstop2h 25mSouthwest
lun. 9/157:45 amMDW - COS
Nonstop2h 25mSouthwest
Deal found 8/13$217
This American Airlines deal was found by Cheapflights users on 8/11. 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.
mié. 8/2712:07 pmCOS - ORD
Nonstop2h 43mAmerican Airlines
mié. 9/310:00 amORD - COS
Nonstop2h 53mAmerican Airlines
Deal found 8/11$221
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/234:54 pmCOS - ORD
1 stop5h 19mAmerican Airlines
mar. 10/289:40 amORD - COS
Nonstop2h 54mAmerican Airlines
Deal found 8/12$222

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 agosto 14, 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 - MDW

COSMDW

Colorado Springs

mié. 10/22

1:55 pm-5:15 pm

Nonstop2h 20m

Chicago Midway

mar. 10/28

4:00 pm-5:35 pm

Nonstop2h 35m

$137

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

mié. 10/22

1:55 pm-5:15 pm

Nonstop2h 20m

Chicago Midway

lun. 10/27

12:00 pm-1:35 pm

Nonstop2h 35m

$177

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

vie. 10/3

2:10 pm-5:30 pm

Nonstop2h 20m

Chicago Midway

mar. 10/7

4:00 pm-5:35 pm

Nonstop2h 35m

$183

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

sáb. 9/13

5:10 pm-11:59 pm

1 stop5h 49m

Chicago O'Hare Intl

mar. 9/16

7:50 pm-9:54 pm

Nonstop3h 04m

$187

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

lun. 9/8

5:10 pm-11:59 pm

1 stop5h 49m

Chicago O'Hare Intl

mar. 9/9

9:07 am-10:56 am

Nonstop2h 49m

$187

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

mié. 9/24

12:02 pm-3:43 pm

Nonstop2h 41m

Chicago O'Hare Intl

sáb. 9/27

5:01 am-9:05 am

1 stop5h 04m

$187

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

dom. 10/19

1:45 pm-10:55 pm

1 stop8h 10m

Chicago Midway

mié. 10/22

4:00 pm-5:35 pm

Nonstop2h 35m

$193

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

dom. 10/5

7:00 pm-12:35 am

1 stop4h 35m

Chicago Midway

mié. 10/8

4:00 pm-5:35 pm

Nonstop2h 35m

$193

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

mié. 9/17

5:05 pm-11:05 pm

1 stop5h 00m

Chicago O'Hare Intl

vie. 9/19

6:55 pm-10:35 pm

1 stop4h 40m

$203

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

sáb. 9/6

11:01 am-8:01 pm

1 stop8h 00m

Chicago O'Hare Intl

mar. 9/9

9:56 am-11:51 am

Nonstop2h 55m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 31 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 August 8, 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 agosto 14, 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 agosto 14, 2025.

The most flights from COS to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 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 agosto 14, 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
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 4 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 American Airlines. Our recent data shows that you can find tickets from as low as $217 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $265 and $287 round-trip. Users have found that American Airlines is 39% 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 (84%), Emirates (82%), SkyWest Airlines( 64%).

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

    Looking at all options, your cheapest flight can be booked for $135. While the most popular route (Colorado Springs - Chicago O'Hare Intl) can be booked for $177 on average our data indicates $490 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$217Average$321FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$265Average$336FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$287Average$402FlexibilityNo cancel feeOn-time69%

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