Cheap flights from Colorado Springs to Chicago from $103
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Colorado Springs to Chicago departing on 7/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Colorado Springs to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
American Airlines flights from Colorado Springs to Chicago
Our best American Airlines deals on Colorado Springs to Chicago flight tickets
Delta flights from Colorado Springs to Chicago
Our best Delta deals on Colorado Springs to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Colorado Springs to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago?
The month of February is, on average, the cheapest month to fly to Chicago from Colorado Springs, with most prices found around $309. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Colorado Springs to Chicago during January average around $316.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $290. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Colorado Springs to Chicago for around $511.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Colorado Springs to Chicago during this time can be as low as $183. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $650.
What is the cheapest Colorado Springs to Chicago flight route?
Fly from Colorado Springs to Chicago Midway for the best Colorado Springs - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Colorado Springs when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $393 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Colorado Springs for as low as $155 on momondo.
What cabin class options are available on Colorado Springs to Chicago flights?
There are 4 cabin classes available to choose from on Colorado Springs to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Colorado Springs to Chicago flights?
No. A direct flight is the cheapest option for a flight between Colorado Springs to Chicago.
How have Colorado Springs to Chicago flight prices changed over time?
As of June 2025, prices for Colorado Springs to Chicago flights are approximately 14% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Colorado Springs to Chicago?
Southwest, United Airlines, and Delta are the most popular carriers operating from Colorado Springs to Chicago
What airlines fly to Chicago?
Frontier, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Colorado Springs according to our data. Frontier is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Colorado Springs to Chicago on average per day?
As of June 2025, 6 flights take off from Colorado Springs and land in Chicago each day. The most common flight departure time for this route is 12:00PM, with 70% of daily flights taking off in the afternoon.
How many flights depart from Colorado Springs to Chicago on average per week?
As of June 2025, there are 46 flights per week flying from Colorado Springs to Chicago. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.
When to book flights from Colorado Springs to Chicago
Cheap Colorado Springs to Chicago (COS to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Colorado Springs to Chicago
How far is Colorado Springs to Chicago by plane?
Colorado Springs and Chicago are 927.0 mi apart from one another. Typically, this will take 2h 20m by plane in normal conditions.
When did momondo last update prices for flights from Colorado Springs Airport to Chicago?
Prices for flights from Colorado Springs Airport to Chicago are updated daily.
How many operators does momondo search for flights from Colorado Springs Airport to Chicago?
As of June 2025, there are 3 operators available to choose from for flights from Colorado Springs Airport to Chicago.
How old do you have to be to fly from Colorado Springs Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Colorado Springs Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Colorado Springs to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Colorado Springs to Chicago is Embraer 175 (Enhanced Winglets), representing 34.63% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet 700 at 18.54%, Boeing 737-700 at 16.34%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 13.90%.
What is the most popular airline from Colorado Springs to Chicago?
momondo data reveals that the most frequently booked airline on the route from Colorado Springs to Chicago is United Airlines, representing 52% of all bookings. The subsequent popular airlines are Southwest at 41% and American Airlines at 7%.
Best airlines flying from Colorado Springs to Chicago
Compare and see reviews for airlines that fly from Colorado Springs to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $217 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $267 | Free Cancellation | Rating 7.4 8,801 reviews | |||
| PriceFrom $283 | Free Cancellation | Rating 8.0 4,278 reviews |
Southwest Flights From Colorado Springs to Chicago
Across 13 Southwest flights from Colorado Springs to Chicago this week, the average price was $336, with the best Southwest deals starting from $283 round-trip. 4,278 users have rated Southwest on momondo, with an average score of 8.0/10.
United Airlines Flights From Colorado Springs to Chicago
United Airlines (7.4/10 from 8,801 reviews) operates around 12 flights from Colorado Springs to Chicago in any given week. The average United Airlines airfare for this route is around $392, with deals from around $267 rare but found on momondo. Referenced prices are for round-trip Colorado Springs to Chicago flight searches in the last 72 hours.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Colorado Springs to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Colorado Springs to Chicago for you.
Can I find flights from Colorado Springs to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Colorado Springs with this policy.
How can momondo help me find flights from Colorado Springs to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Colorado Springs to Chicago.
I’m not ready to book a flight from Colorado Springs to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Colorado Springs to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.