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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 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 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

September 9 - September 10

Cheapest

Best

COS - Chicago

$353

$259

Round trip

July 15 - July 29

COS - Chicago

$180

$271

Round trip

October 22 - October 24

COS - Chicago

$242

$272

Round trip

September 9 - September 11

COS - Chicago

$195

$273

Round trip

October 10 - October 17

COS - Chicago

$229

$273

Round trip

September 5 - September 8

COS - Chicago

$203

$279

Round trip

July 14 - July 21

Earliest

COS - Chicago

$297

$282

Round trip

July 14 - July 28

Earliest

COS - Chicago

$266

$282

Round trip

July 15 - July 22

COS - Chicago

$297

$282

Round trip

July 21 - July 28

COS - Chicago

$290

$282

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Colorado Springs to Chicago

Right now, 13% of recent fares from Colorado Springs to Chicago are classified as a good price. For travelers looking for cheap flights from Colorado Springs to Chicago, fares typically range from $227–$406, with a median of $360. Current fares are below the typical level.

A typical journey from Colorado Springs to Chicago takes about 4h 55m, including connections. This is considered a short-haul route, covering a distance of 1472 kilometers.

Most itineraries for flights from Colorado Springs to Chicago connect at least once, with only 29.3% of recent fares being non-stop. When connecting, the typical 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. Other budget-friendly months include February, with a median of $176, and January, where the median fare is $267.

How much is a round trip from Colorado Springs to Chicago

Regular price: $297 - $441

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

The regular price range for this route is between $297 and $441. The current lowest deal is $259 with Southwest Airlines, for travel from September 9 to September 10, 2026.

now $259

Low $297

High $441

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

Tue, Jun 30

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

United Airlines

$366

$369

One-way

Wed, Jul 1

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

American Airlines

$335

$308

One-way

Sat, Jul 4

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

$324

$289

One-way

Sat, Jul 4

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

$324

$289

One-way

Sat, Jul 4

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

United Airlines

$183

$315

One-way

Sat, Jul 11

⌛ Last-Minute

COS - Chicago

Colorado Springs (COS) - Chicago (ORD)

United Airlines

$312

$332

One-way

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

3 nights

Aug 8 - Aug 11

$404 → $294

27%

6 nights

Dec 3 - Dec 9

$388 → $290

25%

4 nights

Aug 6 - Aug 10

$391 → $295

25%

1 night

Sep 9 - Sep 10

$353 → $259

27%

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 from Colorado Springs to Chicago are below the typical level, with 13% good prices.

📅 Best time to fly

October is historically the cheapest month to fly.

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

⏱️ Flight duration

Flights are typically 4h 55m long.

The typical flight duration from Colorado Springs to Chicago is 4h 55m.

✈️ Airlines & availability

Connecting flights are more common than direct flights.

Connecting flights are more common, making up 70.7% of recent deals.

🏆 Airline highlight

Southwest Airlines offers direct flights.

Southwest Airlines is one of the carriers that historically offers direct flights on this route.

🎯 Booking tip

Deals appear frequently for this route.

Historically, deals for flights from Colorado Springs to Chicago appear frequently, about 0.8 times per day.

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 offers excellent proximity to Chicago with high-frequency flight options and direct rail access.

📍 ~135 km from Chicago (reachable by rail; travel time can be affected by heavy traffic on the I-94 corridor).

💸 Flights from ~$219

South Bend International (SBN)

South Bend International is geographically the closest alternative to Chicago, with direct commuter rail links.

📍 ~120 km from Chicago (reachable by rail; fewer direct flight destinations compared to Milwaukee or Chicago).

💸 Flights from ~$291

Gerald R. Ford International (GRR)

Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes for travelers.

📍 ~200 km from Chicago (requires a significant drive, over 2 hours, from central Chicago).

💸 Flights from ~$335

Dane County Regional (MSN)

Dane County Regional is a reliable regional airport with consistent service and less congestion than major hubs.

📍 ~205 km from Chicago (distance exceeds 190km, making it a secondary choice to MKE).

💸 Flights from ~$309

Fort Wayne International (FWA)

Fort Wayne International provides stable regional service and is an alternative for southeastern Chicago suburbs.

📍 ~240 km from Chicago (significant distance from Chicago and limited flight frequency).

💸 Flights from ~$338

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 best prices for flights from Colorado Springs to Chicago are found when booking 14-27 days in advance, with an average price of $309. Booking 7-13 days out typically sees an average price of $395. For those booking 0-6 days before departure, the average price rises to $470. Planning your trip within the 14-27 day window generally offers the most favorable rates across the trailing quarter.

Across the trailing quarter, a good price for a flight from Colorado Springs to Chicago is considered to be $227 or less. The median price for this route historically stands at $360. Prices typically range, with 75% of fares being $406 or less. Aiming for a fare around $227 can help secure a more economical journey.

Historically, October is the cheapest month to fly from Colorado Springs to Chicago, with a median price of $135. February also offers lower fares, with a median price of $176. The annual median price for this route is $360, indicating that October and February provide significant savings compared to other times of the year.

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