$119+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
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.Cheapflights Tip: The best prices from Colorado Springs to Chicago are usually found in February or January, booked 30 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 June 12, 2025.
Round-trip from | $251 (Southwest) |
|---|---|
One-way from | $124 (Mytrip) |
Popular in | November |
Cheapest in | February |
Average price | $341 |
Good round-trip deal | $291 or less |
Good one-way deal | $158 or less |
Find flight deals from Colorado Springs to Chicago
Cheapest flights from Colorado Springs to ChicagoExplore 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 June 12, 2025.
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 June 12, 2025.
This Southwest deal was found by Cheapflights users on 6/12. 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.
This American Airlines deal was found by Cheapflights users on 6/11. 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.
This United Airlines deal was found by Cheapflights users on 6/12. 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.
This Delta deal was found by Cheapflights users on 6/10. 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.
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/9. 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.
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight 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 June 12, 2025.
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
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Wed 8/6
11:55 am-3:15 pm
Nonstop2h 20m
Chicago Midway
Sat 8/9
5:35 pm-7:05 pm
Nonstop2h 30m
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Sat 8/30
12:07 pm-3:50 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sat 9/6
9:56 am-11:51 am
Nonstop2h 55m
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Wed 8/6
12:05 pm-3:45 pm
Nonstop2h 40m
Chicago O'Hare Intl
Sat 8/9
9:15 am-11:08 am
Nonstop2h 53m
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Sat 8/9
6:00 am-3:27 pm
1 stop8h 27m
Chicago Midway
Wed 8/20
12:43 pm-8:41 pm
1 stop8h 58m
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Wed 8/6
6:00 am-4:33 pm
2 stops9h 33m
Chicago O'Hare Intl
Sat 8/9
6:00 am-9:59 am
1 stop4h 59m
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Fri 7/11
5:09 pm-6:03 am
2 stops11h 54m
Chicago O'Hare Intl
Fri 7/18
7:08 am-4:19 pm
2 stops10h 11m
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Fri 7/4
6:55 am-3:20 pm
1 stop7h 25m
Chicago O'Hare Intl
Mon 7/7
5:25 pm-12:55 am
1 stop8h 30m
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Mon 11/17
4:52 pm-11:43 pm
2 stops29h 51m
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Tue 8/12
11:55 am-3:15 pm
Nonstop2h 20m
Colorado SpringsChicago
COS - ORD
COSORD
Colorado Springs
Fri 10/31
9:22 am-1:13 pm
Nonstop2h 51m
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.
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 June 9, 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 30 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 June 12, 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 8% 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 June 12, 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 (3 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 June 12, 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.
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
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.
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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.
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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$217 | Average$401 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$392 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$283 | Average$336 | FlexibilityNo cancel fee | On-time63% |