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 were direct. For flights that include stopovers, the median number of stopovers was one. Travelers should consider this when planning their journey.

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, at 5 hours and 12 minutes. The distance covered on this route is approximately 1472 kilometers.

How often do Colorado Springs to Chicago flight prices drop?

Historically, price drops for flights from Colorado Springs to Chicago are frequent. This suggests that travelers may often find opportunities for more favorable pricing on this route. Monitoring prices can be beneficial for securing a good deal.

Flights From Colorado Springs

To Chicago

Cheap Flights from Colorado Springs to Chicago

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Deals from

Colorado Springs

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Prices updated today

405 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Colorado Springs to Chicago

Explore current cheapest deals departing from Colorado Springs to Chicago

Round trip

Sort by: Cheapest

December 10 - December 12

Cheapest

COS - Chicago

$243

$232

Round trip

November 22 - December 9

Best

COS - Chicago

$322

$239

Round trip

August 18 - August 19

COS - Chicago

$269

$243

Round trip

August 20 - August 27

COS - Chicago

$250

$243

Round trip

August 19 - August 29

COS - Chicago

$187

$243

Round trip

August 13 - August 20

COS - Chicago

$252

$243

Round trip

September 16 - September 22

COS - Chicago

$190

$243

Round trip

October 17 - October 20

COS - Chicago

$207

$243

Round trip

December 5 - December 12

COS - Chicago

$234

$243

Round trip

August 8 - August 22

Earliest

COS - Chicago

$216

$252

Round trip

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Colorado Springs to Chicago: Overview

Insights for flights from Colorado Springs to Chicago

For cheap flights from Colorado Springs to Chicago, about 15% of recent fares have been classified as a good price. Right now, fares are above the typical level for this route. Prices typically range from $230–$406, with a median of $351.

A typical journey from Colorado Springs to Chicago takes about 4h 55m, including connections. Given that most itineraries connect at least once, this duration accounts for the layover time. The overall distance between Colorado Springs and Chicago is 1472 km, classifying this as a short-haul route.

Most itineraries for flights from Colorado Springs to Chicago connect at least once, with only 29.2% of recent fares being non-stop. When connecting, the median number of stopovers is 1.

When is the cheapest time to fly from Colorado Springs to Chicago? The most affordable month to fly is typically October, with a median fare of $135. February also offers lower prices, with a median of $176, followed by January at $267.

How much is a round trip from Colorado Springs to Chicago

Regular price: $142 - $381

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

The regular price range for flights from Colorado Springs to Chicago is between $142 and $381. The current lowest deal is $242 with American Airlines for travel from Sep 16-Sep 22.

now $242

Low $142

High $381

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

Southwest Airlines

United Airlines

Last-minute flights going from Colorado Springs to Chicago

Sat, Aug 1

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

United Airlines

$475

$360

One-way

Sat, Aug 1

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

$665

$479

One-way

Sat, Aug 1

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

$660

$479

One-way

Sun, Aug 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$527

$486

One-way

Tue, Aug 4

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$460

$362

One-way

Tue, Aug 4

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$479

$441

One-way

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

3 nights

Aug 1 - Aug 4

$665 → $479

28%

4 nights

Aug 1 - Aug 5

$660 → $479

27%

2 nights

Aug 15 - Aug 17

$430 → $252

41%

4 nights

Aug 25 - Aug 29

$405 → $243

40%

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 from Colorado Springs to Chicago are above the typical level for this route.

📅 Best time to fly

October is historically the cheapest month to fly

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

⏱️ Flight duration

Direct flights take 4h 55m

The typical direct flight from Colorado Springs to Chicago takes 4 hours and 55 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route

Connecting flights are dominant on this route, with a median of 1 stopover when connecting.

🏆 Airline highlight

Southwest Airlines offers direct flights

Southwest Airlines offers direct flights from Colorado Springs to Chicago, providing a convenient travel option.

🎯 Booking tip

Deals appear frequently on this route

Deals for flights from Colorado Springs to Chicago appear frequently, with good prices available 15% of the time.

Colorado Springs main airports to depart from

Colorado Springs (COS)

Cheapest

Colorado Springs Airport is a good choice for flights to Chicago, offering a budget-friendly option.

📍 ~12 km from Colorado Springs city center (reachable by car)

💸 Flights from ~$259

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a good option for flights from Colorado Springs to Chicago, with prices from $259.

📍 ~15 km from Chicago city center (reachable by car)

💸 Flights from ~$259

Chicago Rockford International (RFD)

Chicago Rockford International offers another arrival choice for your trip from Colorado Springs to Chicago.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$290

O Hare International (ORD)

O Hare International is a convenient arrival airport for travelers flying from Colorado Springs to Chicago.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$271

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International Airport is a major international airport with significant carrier presence and direct flight options.

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

💸 Flights from ~$178

Gerald R. Ford International (GRR)

Gerald R. Ford International Airport is the second largest airport in Michigan with a robust domestic network.

📍 ~250 km from Chicago (reachable by car)

💸 Flights from ~$274

Dane County Regional (MSN)

Dane County Regional Airport is a reliable regional hub with efficient operations and good amenities.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$308

South Bend International (SBN)

South Bend International Airport is geographically the closest alternative airport to the Chicago metro area.

📍 ~120 km from Chicago (reachable by car or train)

💸 Flights from ~$243

Fort Wayne International (FWA)

Fort Wayne International Airport offers multiple cabin classes and solid connectivity for eastern domestic destinations.

📍 ~250 km from Chicago (reachable by car)

💸 Flights from ~$318

Business & First Class Flight Deals to Chicago

Chicago, United States

43% AI deal score

$937

From COS

Elite

Jun 19

Chicago, United States

37% AI deal score

$1,184

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Colorado Springs to Chicago is typically 14-27 days before departure. During this period, the average price for a flight is around $309. Booking within 0-6 days of departure usually sees prices rise to approximately $470. Even booking 60+ days out tends to result in higher average prices, around $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 observed prices being $406 or less.

Historically, the cheapest months to fly from Colorado Springs to Chicago are October, with a median price of $135, and February, with a median price of $176. January also shows a median price of $267. The annual median price for this route is $351, indicating significant savings during these months.

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