What percentage of Colorado Springs to Chicago flights are direct?

In the trailing 90 days, approximately 29.2% of flights from Colorado Springs to Chicago have been direct. For flights that include stopovers, the median number of stopovers is one. This indicates that while direct options are available, a significant portion of flights on this route involve at least one connection.

How long is the flight from Colorado Springs to Chicago?

The typical direct flight from Colorado Springs to Chicago has a median duration of 2 hours and 46 minutes. For flights with one stop, the median duration is considerably longer, averaging 5 hours and 12 minutes. The total air distance covered on this route is 1472 kilometers. Travelers should factor in these durations when planning their journey.

How often do Colorado Springs to Chicago flight prices drop?

Historically, flight prices for the Colorado Springs to Chicago route have shown frequent drops. This indicates that travelers may often find opportunities to secure better deals. Monitoring prices regularly can be beneficial for those looking to purchase tickets for this route.

Flights From Colorado Springs

To Chicago

Cheap Flights from Colorado Springs to Chicago

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RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated today

462 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 15, 2026.)

Today’s best flight deals from Colorado Springs to Chicago

Explore current cheapest deals departing from Colorado Springs to Chicago

2027-02-13 – 2027-02-17
COS - Chicago
73% AI deal score
$347
$272
Round trip
2026-10-07 – 2026-10-14
COS - Chicago
69% AI deal score
$339
$281
Round trip
2026-10-01 – 2026-10-06
COS - Chicago
45% AI deal score
$189
$292
Round trip
2026-10-01 – 2026-10-05
COS - Chicago
46% AI deal score
$198
$292
Round trip
2026-10-26 – 2026-10-29
COS - Chicago
43% AI deal score
$184
$292
Round trip
2026-11-05 – 2026-11-07
COS - Chicago
46% AI deal score
$174
$292
Round trip
2026-10-22 – 2026-10-27
COS - Chicago
41% AI deal score
$187
$293
Round trip
2026-10-10 – 2026-10-17
COS - Chicago
65% AI deal score
$312
$301
Round trip
2026-10-05 – 2026-10-19
COS - Chicago
48% AI deal score
$272
$301
Round trip
2026-10-06 – 2026-10-20
COS - Chicago
48% AI deal score
$272
$301
Round trip

Colorado Springs to Chicago: Overview

Insights for flights from Colorado Springs to Chicago

Right now, 15% of recent fares for flights from Colorado Springs to Chicago are classified as a good price. Fares typically range from $230–$406, with a median of $351. Current fares are significantly above the typical level, suggesting that now might not be the optimal time to secure the cheapest flights from Colorado Springs to Chicago. New deals appear almost daily, so monitoring prices can be beneficial.

When considering the cheapest time to fly from Colorado Springs to Chicago, October stands out with a median fare of just $135. Following closely, February offers a median fare of $176, making it another cost-effective option. January also presents a more affordable choice, with a median fare of $267, indicating that these months are generally more budget-friendly for this route.

A typical journey from Colorado Springs to Chicago takes about 4h 55m, including connections. Most itineraries for this route connect at least once, with the majority of connecting flights involving one stopover. Only 29.2% of recent fares are for direct flights from Colorado Springs to Chicago, meaning you'll likely have a layover on your trip.

The distance between Colorado Springs and Chicago is approximately 1,472 kilometers. This classifies the route as a short-haul journey. While not a long-distance flight, the typical journey time of nearly five hours reflects the prevalence of connecting itineraries.

How much is a round trip from Colorado Springs to Chicago

Regular price: $285 - $388

Prices are currently below the regular range for flights from Colorado Springs to Chicago.

The regular price range for flights from Colorado Springs to Chicago is typically between $285 and $388. The current lowest deal is $257 with Allegiant Air, for travel from Dec 3-Dec 9.

now $257

Low $285

High $388

The cheapest time to fly from Colorado Springs to Chicago

The cheapest month to fly from Colorado Springs to Chicago is October, with a median price of $135. The most expensive month is December, with a median price of $591. Prices are generally lower from January to November.

October

Cheapest

Flights from $135

December

Most Expensive

Flights from $591

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Colorado Springs to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Colorado Springs to Chicago

Thu, Oct 1

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$189

$292

One-way

Thu, Oct 1

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

United Airlines

$198

$292

One-way

Fri, Oct 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$301

$329

One-way

Fri, Oct 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$300

$329

One-way

Fri, Oct 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

United Airlines

$198

$362

One-way

Fri, Oct 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$355

$363

One-way

Biggest price drops on these dates for flights from Colorado Springs to Chicago

4 nights

Mar 22 - Mar 26

$589 → $465

21%

3 nights

Sep 16 - Sep 19

$614 → $519

15%

4 nights

Feb 20 - Feb 24

$352 → $265

25%

3 nights

Feb 20 - Feb 23

$351 → $265

25%

Popular Airports to fly from Colorado Springs to Chicago

Colorado Springs - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares for Colorado Springs to Chicago are above the typical level at $351.

📅 Best time to fly

October is historically the cheapest month to fly.

Historically, October is the cheapest with a median price of $135 for Colorado Springs to Chicago.

⏱️ Flight duration

Flights typically take 4h 55m.

Flights from Colorado Springs to Chicago typically take 4h 55m, covering a distance of 1472 km.

✈️ Airlines & availability

29.2% of recent flights are direct.

Historically, 29.2% of flights from Colorado Springs to Chicago are direct, with frequent deals.

🏆 Airline highlight

American Airlines offers direct flights.

American Airlines is one of the carriers offering direct flights on the Colorado Springs to Chicago route.

🎯 Booking tip

Consider booking connecting flights.

Connecting flights are dominant on this route, with typically 1 stopover when connecting.

Colorado Springs main airports to depart from

Colorado Springs (COS)

Cheapest

Colorado Springs Airport (COS) is a convenient option for flights from Colorado Springs to Chicago.

📍 ~11 km from city center (reachable by car)

💸 Flights from ~$235

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International Airport offers a budget-friendly option for flights from Colorado Springs to Chicago.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$229

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

Milwaukee offers a major international airport with significant carrier presence and direct flight options for Chicago.

📍 ~135 km from Chicago (reachable by car, train)

💸 Flights from ~$275

Business & First Class Flight Deals to Chicago

$664

Save $124

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from Colorado Springs to Chicago between 14 and 27 days in advance typically yields the best prices. During this period, the average price is around $309. If you book within 0-6 days of departure, the average price can increase to approximately $470. Even booking 60+ days out tends to be more expensive, with an average price of $373.

Across the trailing quarter, a good price for a flight from Colorado Springs to Chicago is considered to be $230 or less. The median price for this route over the same period was $351. Prices can go higher, with 75% of prices observed at $406 or less. This threshold helps travelers identify competitive deals.

Historically, October has been the cheapest month to fly from Colorado Springs to Chicago, with a median price of $135. February also offers lower prices, with a median of $176. While January's median price is $267, it is also noted as the most expensive month, suggesting price variability within that month. The annual median price for this route is $351.

Related routes

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Flights to Chicago from other cities

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Colorado Springs to Chicago: Overview

Insights for flights from Colorado Springs to Chicago

How much is a round trip from Colorado Springs to Chicago

Regular price: $285 - $388

Prices are currently below the regular range for flights from Colorado Springs to Chicago.

The regular price range for flights from Colorado Springs to Chicago is typically between $285 and $388. The current lowest deal is $257 with Allegiant Air, for travel from Dec 3-Dec 9.

now $257

Low $285

High $388

The cheapest time to fly from Colorado Springs to Chicago

October

Cheapest

Flights from $135

December

Most Expensive

Flights from $591

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Colorado Springs to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Colorado Springs to Chicago

Thu, Oct 1

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$189

$292

One-way

Thu, Oct 1

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

United Airlines

$198

$292

One-way

Fri, Oct 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$301

$329

One-way

Fri, Oct 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$300

$329

One-way

Fri, Oct 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

United Airlines

$198

$362

One-way

Fri, Oct 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$355

$363

One-way

Biggest price drops on these dates for flights from Colorado Springs to Chicago

4 nights

Mar 22 - Mar 26

$589 → $465

21%

3 nights

Sep 16 - Sep 19

$614 → $519

15%

4 nights

Feb 20 - Feb 24

$352 → $265

25%

3 nights

Feb 20 - Feb 23

$351 → $265

25%

Popular Airports to fly from Colorado Springs to Chicago