Are direct flights from Colorado Springs to Chicago always the best option?

Direct flights offer convenience by reducing travel time and avoiding layovers. However, connecting flights can often be more affordable, especially if you are flexible with your schedule. The 'best' option depends on your priorities regarding cost versus travel time.

Can flexible travel dates help on Colorado Springs to Chicago flights?

Yes, being flexible with your travel dates can significantly impact flight prices. Flying on weekdays or during off-peak seasons often results in lower fares compared to weekends or popular travel periods. Even shifting your departure or return by a day or two may yield savings.

What extra costs should I check before booking Colorado Springs to Chicago flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines may also charge for printing boarding passes at the airport. Factor these into your total travel budget to avoid surprises.

Flights From Colorado Springs

To Chicago

Cheap Flights from Colorado Springs to Chicago

Browse current best options from Colorado Springs. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Colorado Springs

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

Prices updated 7 days ago

482 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Colorado Springs to Chicago

Explore current cheapest deals departing from Colorado Springs to Chicago

2026-12-02 – 2026-12-08
COS - Chicago
47% AI deal score
$172
$253
Round trip
2026-12-07 – 2026-12-14
COS - Chicago
47% AI deal score
$172
$253
Round trip
2026-12-01 – 2026-12-07
COS - Chicago
68% AI deal score
$298
$263
Round trip
2026-12-11 – 2026-12-15
COS - Chicago
46% AI deal score
$181
$273
Round trip
2027-02-06 – 2027-02-13
COS - Chicago
47% AI deal score
$278
$319
Round trip
2027-02-17 – 2027-02-24
COS - Chicago
47% AI deal score
$276
$319
Round trip
2027-02-16 – 2027-02-23
COS - Chicago
47% AI deal score
$276
$327
Round trip
2027-02-14 – 2027-02-21
COS - Chicago
43% AI deal score
$170
$383
Round trip
2027-02-07 – 2027-02-14
COS - Chicago
44% AI deal score
$278
$393
Round trip
2027-02-15 – 2027-02-22
COS - Chicago
44% AI deal score
$275
$408
Round trip

Colorado Springs to Chicago: Overview

Insights for flights from Colorado Springs to Chicago

For cheap flights from Colorado Springs to Chicago, right now fares are significantly below the typical level. Over the past 90 days, only 6% of recent fares were classified as a good price. Prices for this route typically range from $323–$435, with a median of $357.

A typical journey from Colorado Springs to Chicago takes about 4h 55m, including connections. Given that almost all itineraries are non-stop, this duration largely reflects the direct flight time. Most itineraries connect at least once, with a median of 1 stopover when connecting.

The distance between Colorado Springs and Chicago is 1472 km, classifying this as a short-haul route.

When is the cheapest time to fly from Colorado Springs to Chicago? The data indicates that January is typically the most affordable month, with a median fare of $321. Following closely are September and August, both with median fares of $323.

How much is a round trip from Colorado Springs to Chicago

Regular price: $226 - $372

Prices are currently within the regular range.

The regular price range for flights from Colorado Springs to Chicago is typically between $226 and $372. The current lowest deal is $231 with Allegiant Air for travel from Jan 21-Feb 3.

now $231

Low $226

High $372

The cheapest time to fly from Colorado Springs to Chicago

The cheapest month to fly from Colorado Springs to Chicago is January, with a median price of $321. The most expensive month is December, with a median price of $654. Prices are generally lower from January to November.

January

Cheapest

Flights from $321

December

Most Expensive

Flights from $654

Jan

Feb

Aug

Sep

Oct

Nov

Dec

Direct flights from Colorado Springs to Chicago

United Airlines

Last-minute flights going from Colorado Springs to Chicago

Mon, Nov 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

Southwest Airlines

$378

$583

One-way

Thu, Nov 5

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (RFD)

Allegiant Air

$296

$477

One-way

Sun, Nov 8

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (RFD)

Allegiant Air

$285

$513

One-way

Mon, Nov 9

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

Allegiant Air

$358

$403

One-way

Mon, Nov 9

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$187

$503

One-way

Tue, Nov 10

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$186

$503

One-way

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

6 nights

Jan 28 - Feb 3

$298 → $240

20%

6 nights

Jan 21 - Jan 27

$291 → $250

14%

13 nights

Jan 21 - Feb 3

$265 → $231

13%

3 nights

Jan 10 - Jan 13

$291 → $257

12%

Popular Airports to fly from Colorado Springs to Chicago

Colorado Springs - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares for flights from Colorado Springs to Chicago are below the typical level.

📅 Best time to fly

Cheapest flights in January, September, August

Historically, the cheapest flights from Colorado Springs to Chicago are in January ($321), September ($323), and August ($323).

⏱️ Flight duration

Typically 4h 55m

The median flight duration from Colorado Springs to Chicago is 4 hours and 55 minutes.

✈️ Airlines & availability

76.1% of recent flights are direct

76.1% of recent flights from Colorado Springs to Chicago are direct, with 1 stopover when connecting.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights from Colorado Springs to Chicago Rockford International.

🎯 Booking tip

Deals are rare

Deals for flights from Colorado Springs to Chicago have historically been rare in the last 30 days.

Colorado Springs main airports to depart from

Colorado Springs (COS)

Cheapest

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

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

💸 Flights from ~$248

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Consider Chicago Rockford International for potentially cheaper flights to the Chicago area from Colorado Springs.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$221

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 train or car)

💸 Flights from ~$411

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Colorado Springs to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From COS

Elite

Jan 06

Chicago, United States

76% AI deal score

$1,044

$670

Save $374

From COS

Elite

Nov 02

Chicago, United States

73% AI deal score

$1,351

$1,001

Save $350

From COS

Elite

Nov 07

Chicago, United States

49% AI deal score

$1,041

$946

Save $95

From COS

Elite

Nov 04

Chicago, United States

41% AI deal score

$998

From COS

Elite

Nov 02

Chicago, United States

37% AI deal score

$1,474

From COS

Elite

Nov 06

Chicago, United States

26% AI deal score

$2,415

From COS

Elite

Nov 02

Chicago, United States

26% AI deal score

$3,232

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking sites can also help uncover better deals. Setting up price alerts may notify you when fares drop for your desired route.

Booking flights in advance, often several weeks or months, may result in lower prices. However, prices can fluctuate, so monitoring fare trends can be beneficial. Mid-week bookings are sometimes associated with better deals than weekend bookings.

Comparing nearby airports at both your origin and destination can sometimes reveal more economical flight options. While it may add to travel time, the potential savings on airfare can be significant. Always factor in ground transportation costs when considering alternative airports.

Related routes

More routes from Colorado Springs

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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

The distance between Colorado Springs and Chicago is 1472 km, classifying this as a short-haul route.

How much is a round trip from Colorado Springs to Chicago

Regular price: $226 - $372

Prices are currently within the regular range.

The regular price range for flights from Colorado Springs to Chicago is typically between $226 and $372. The current lowest deal is $231 with Allegiant Air for travel from Jan 21-Feb 3.

now $231

Low $226

High $372

The cheapest time to fly from Colorado Springs to Chicago

January

Cheapest

Flights from $321

December

Most Expensive

Flights from $654

Jan

Feb

Aug

Sep

Oct

Nov

Dec

Direct flights from Colorado Springs to Chicago

United Airlines

Last-minute flights going from Colorado Springs to Chicago

Mon, Nov 2

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

Southwest Airlines

$378

$583

One-way

Thu, Nov 5

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (RFD)

Allegiant Air

$296

$477

One-way

Sun, Nov 8

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (RFD)

Allegiant Air

$285

$513

One-way

Mon, Nov 9

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (MDW)

Allegiant Air

$358

$403

One-way

Mon, Nov 9

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$187

$503

One-way

Tue, Nov 10

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$186

$503

One-way

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

6 nights

Jan 28 - Feb 3

$298 → $240

20%

6 nights

Jan 21 - Jan 27

$291 → $250

14%

13 nights

Jan 21 - Feb 3

$265 → $231

13%

3 nights

Jan 10 - Jan 13

$291 → $257

12%

Popular Airports to fly from Colorado Springs to Chicago