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, travelers typically experience one stop. This means that a significant portion of flights on this route will involve at least one connection.

How long is the flight from Colorado Springs to Chicago?

The median direct flight from Colorado Springs to Chicago typically takes 2 hours and 46 minutes. For flights with one stop, the median duration is considerably longer, averaging 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, flight prices for the Colorado Springs to Chicago route tend to drop frequently. This indicates that travelers may often find opportunities for price reductions. Monitoring prices regularly can be beneficial for securing a more favorable fare.

Flights From Colorado Springs

To Chicago

Cheap Flights from Colorado Springs to Chicago

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Deals from

Colorado Springs

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

Prices updated today

444 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 9, 2026.)

Today’s best flight deals from Colorado Springs to Chicago

Explore current cheapest deals departing from Colorado Springs to Chicago

2026-09-05 – 2026-09-06
COS - Chicago
47% AI deal score
$191
$243
Round trip
2026-09-05 – 2026-09-06
COS - Chicago
43% AI deal score
$182
$243
Round trip
2026-12-09 – 2026-12-16
COS - Chicago
48% AI deal score
$226
$245
Round trip
2026-08-22 – 2026-08-25
COS - Chicago
66% AI deal score
$273
$246
Round trip
2026-09-12 – 2026-09-19
COS - Chicago
47% AI deal score
$182
$246
Round trip
2026-09-02 – 2026-09-08
COS - Chicago
47% AI deal score
$183
$246
Round trip
2026-09-21 – 2026-09-23
COS - Chicago
47% AI deal score
$192
$246
Round trip
2026-09-23 – 2026-09-30
COS - Chicago
47% AI deal score
$182
$246
Round trip
2026-09-17 – 2026-09-21
COS - Chicago
47% AI deal score
$192
$246
Round trip
2026-09-16 – 2026-09-21
COS - Chicago
47% AI deal score
$188
$246
Round trip

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 were considered a good price. Right now, fares for this route are above the typical level. 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. Most itineraries connect at least once, with a median of 1 stopover when not flying direct. This indicates that while direct flights from Colorado Springs to Chicago are available, connecting options are more common and contribute to the overall journey time.

The distance between Colorado Springs and Chicago is approximately 1472 kilometers, classifying this as a short-haul route. This distance typically translates to a relatively quick travel experience, even with connections.

When is the cheapest time to fly from Colorado Springs to Chicago? The data indicates that October is the cheapest month to fly, with a median fare of $135. February also offers competitive prices, with a median of $176, followed by January at a median of $267. These months present the best opportunities for finding lower fares.

How much is a round trip from Colorado Springs to Chicago

Regular price: $147 - $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 $147 and $381. The current lowest deal is $243 with United Airlines for travel from Sep 5-Sep 6.

now $243

Low $147

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

American Airlines

Southwest Airlines

Last-minute flights going from Colorado Springs to Chicago

Mon, Aug 10

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$828

$361

One-way

Mon, Aug 10

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$678

$505

One-way

Tue, Aug 11

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$740

$500

One-way

Wed, Aug 12

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$740

$469

One-way

Thu, Aug 13

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$740

$511

One-way

Thu, Aug 13

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$735

$521

One-way

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

2 nights

Aug 10 - Aug 12

$828 → $361

56%

3 nights

Aug 12 - Aug 15

$740 → $469

37%

3 nights

Aug 11 - Aug 14

$740 → $500

32%

3 nights

Aug 13 - Aug 16

$740 → $511

31%

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, with a median price of $351.

📅 Best time to fly

October is historically cheapest at $135

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

⏱️ Flight duration

Typically 4h 55m

Flights from Colorado Springs to Chicago typically take 4 hours and 55 minutes.

✈️ Airlines & availability

Connecting flights are more common

Only 29.2% of recent flights from Colorado Springs to Chicago are direct, making connecting flights more common.

🏆 Airline highlight

United Airlines has a recent deal for $243

United Airlines recently offered a deal for $243 from Colorado Springs to Chicago.

🎯 Booking tip

Deals are frequent on this route

Deals from Colorado Springs to Chicago are frequent, occurring every 30 days.

Colorado Springs main airports to depart from

Colorado Springs (COS)

Cheapest

Colorado Springs Airport is a convenient departure point for flights to Chicago.

📍 ~11 km from Colorado Springs (reachable by car)

💸 Flights from ~$259

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Fly into Chicago Midway International for convenient access to downtown Chicago from Colorado Springs.

📍 ~15 km from city center (reachable by public transport or car)

💸 Flights from ~$259

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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

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

💸 Flights from ~$285

Business & First Class Flight Deals to Chicago

70% AI deal score

$796

$623

Save $173

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 observed was $309. Booking within 0-6 days of departure generally sees prices rise significantly, averaging around $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 historically stands at $351. Prices can go higher, with 75% of observed fares 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 offers relatively lower prices, with a median of $267. The annual median price for this route is $351, indicating that these months offer significant savings.

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: $147 - $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 $147 and $381. The current lowest deal is $243 with United Airlines for travel from Sep 5-Sep 6.

now $243

Low $147

High $381

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

Mon, Aug 10

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$828

$361

One-way

Mon, Aug 10

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$678

$505

One-way

Tue, Aug 11

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$740

$500

One-way

Wed, Aug 12

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$740

$469

One-way

Thu, Aug 13

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$740

$511

One-way

Thu, Aug 13

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

$735

$521

One-way

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

2 nights

Aug 10 - Aug 12

$828 → $361

56%

3 nights

Aug 12 - Aug 15

$740 → $469

37%

3 nights

Aug 11 - Aug 14

$740 → $500

32%

3 nights

Aug 13 - Aug 16

$740 → $511

31%

Popular Airports to fly from Colorado Springs to Chicago