Are there direct flights from Denver to Chicago?

Yes, direct flights are available from Denver to Chicago. Approximately 33.4% of flights on this route historically have been direct. For journeys involving stopovers, the median number of stopovers observed was 2. Travelers seeking a more direct route have a notable percentage of options available.

How long is the flight from Denver to Chicago?

The typical direct flight from Denver to Chicago has a median duration of 5 hours and 28 minutes. This covers a distance of 1437 kilometers. Flights with one stopover, however, historically take considerably longer, with a median duration of 11 hours and 34 minutes. Travelers should factor in these differences when planning their journey.

Are there frequently good prices on flights from Denver to Chicago?

Historically, good prices on flights from Denver to Chicago have been frequent. This route is consistently identified as one where favorable deals appear regularly. Travelers can typically expect to find competitive pricing options when planning their trip between these two cities. The availability of good prices has been a consistent trend across the trailing 30 days.

Flights From Denver

To Chicago

Cheap Flights from Denver to Chicago

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

Deals from

Denver

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

Prices updated 4 days ago

476 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 12, 2026.)

Today’s best flight deals from Denver to Chicago

Explore current cheapest deals departing from Denver to Chicago

2026-11-10 – 2026-12-09
DEN - Chicago
43% AI deal score
$84
$98
Round trip
2026-11-10 – 2026-11-16
DEN - Chicago
44% AI deal score
$102
$103
Round trip
2026-11-10 – 2026-12-02
DEN - Chicago
43% AI deal score
$84
$104
Round trip
2026-11-04 – 2026-12-02
DEN - Chicago
43% AI deal score
$84
$104
Round trip
2026-11-17 – 2026-12-15
DEN - Chicago
43% AI deal score
$84
$104
Round trip
2026-11-18 – 2026-12-15
DEN - Chicago
43% AI deal score
$84
$104
Round trip
2026-11-04 – 2026-11-10
DEN - Chicago
44% AI deal score
$102
$105
Round trip
2026-11-10 – 2026-12-08
DEN - Chicago
43% AI deal score
$84
$105
Round trip
2026-11-11 – 2026-12-02
DEN - Chicago
43% AI deal score
$84
$106
Round trip
2026-11-17 – 2026-12-02
DEN - Chicago
43% AI deal score
$87
$106
Round trip

Denver to Chicago: Overview

Insights for flights from Denver to Chicago

A typical journey from Denver to Chicago, including connections, takes about 5h 26m. Given that most itineraries connect at least once, this median duration accounts for the time spent during layovers. For connecting flights specifically, the median travel time extends to 21h 33m, while non-stop flights have a median duration of 5h 26m.

For travelers seeking cheap flights from Denver to Chicago, fares typically range from $273–$585, with a median of $386. Right now, current fares are above the typical level for this route. New deals for this route appear almost daily, offering frequent opportunities to find better prices.

When is the cheapest time to fly from Denver to Chicago? The data indicates that March is the most affordable month to fly, with a median fare of $243. Following closely, February also offers competitive prices, with a median fare of $265. Another relatively cheaper option is September, where the median fare is $352.

Regarding direct flights from Denver to Chicago, only 33.4% of recent fares are non-stop. This means that most itineraries connect at least once, with the typical connecting flight involving 2 stopovers. Travelers should factor in these connections when planning their journey.

The route from Denver to Chicago covers a distance of 1437 km. This classifies the journey as a short-haul flight, meaning it is a relatively brief trip suitable for quick getaways or business travel within the region.

How much is a round trip from Denver to Chicago

Regular price: $72 - $194

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

The regular price range for flights from Denver to Chicago is $72 to $194. The current lowest deal is $164 with Frontier Airlines, for travel from Feb 6-Feb 24.

now $164

Low $72

High $194

The cheapest time to fly from Denver to Chicago

The cheapest month to fly from Denver to Chicago is March, with a median price of $243. The most expensive month is April, with a median price of $1537. Prices are generally lower from January to December.

March

Cheapest

Flights from $243

April

Most Expensive

Flights from $1,537

Jan

Feb

Mar

Apr

May

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Denver to Chicago

Frontier Airlines

Last-minute flights going from Denver to Chicago

Wed, Oct 21

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$226

$183

One-way

Fri, Oct 23

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$124

$94

One-way

Fri, Oct 23

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$225

$178

One-way

Sat, Oct 24

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$123

$79

One-way

Mon, Oct 26

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$122

$76

One-way

Tue, Oct 27

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$120

$42

One-way

Biggest price drops on these dates for flights from Denver to Chicago

7 nights

Nov 10 - Nov 17

$102 → $40

61%

5 nights

Nov 19 - Nov 24

$199 → $139

30%

3 nights

Nov 21 - Nov 24

$204 → $149

27%

14 nights

Nov 4 - Nov 18

$89 → $40

55%

Popular Airports to fly from Denver to Chicago

Denver - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Denver to Chicago are above the typical level, with a median price of $386.

📅 Best time to fly

Cheapest months: March, February, September

Historically, the cheapest months to fly from Denver to Chicago are March ($243), February ($265), and September ($352).

⏱️ Flight duration

Nonstop flights average 5h 26m

Nonstop flights from Denver to Chicago typically take 5h 26m, while connecting flights average 21h 33m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 66.6% of recent routes, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines provides direct flights on this route, with recent deals as low as $164.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Denver to Chicago are frequently available, especially within a 30-day window.

Denver main airports to depart from

Denver International (DEN)

Cheapest

Denver International Airport is a convenient choice for flights from Denver to Chicago.

📍 ~30 km from city center (reachable by car)

💸 Flights from ~$147

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering a wide range of flights to Chicago.

📍 ~25 km from Chicago city center (reachable by public transport, taxi, car rental).

💸 Flights from ~$40

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 car or train)

💸 Flights from ~$297

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From DEN

Elite

Oct 28

Chicago, United States

80% AI deal score

$1,429

$524

Save $905

From DEN

Elite

Oct 27

Chicago, United States

78% AI deal score

$1,193

$469

Save $724

From DEN

Elite

Dec 07

Chicago, United States

76% AI deal score

$2,195

$1,265

Save $930

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Oct 19

Chicago, United States

75% AI deal score

$1,271

$684

Save $587

From DEN

Elite

Dec 15

Chicago, United States

72% AI deal score

$1,986

$1,193

Save $793

From DEN

Elite

Dec 15

Chicago, United States

72% AI deal score

$1,986

$1,193

Save $793

From DEN

Elite

Dec 14

Chicago, United States

72% AI deal score

$1,986

$1,203

Save $783

From DEN

Elite

Dec 14

Chicago, United States

72% AI deal score

$1,986

$1,203

Save $783

From DEN

Elite

Oct 14

Chicago, United States

72% AI deal score

$1,685

$1,179

Save $506

From DEN

Elite

Dec 07

Chicago, United States

70% AI deal score

$1,987

$1,395

Save $592

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Dec 07

Chicago, United States

70% AI deal score

$2,044

$1,430

Save $614

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Nov 15

Chicago, United States

69% AI deal score

$1,852

$1,451

Save $401

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal window for booking flights from Denver to Chicago is typically 28-59 days prior to departure. During this period, the average price observed was around $469. Prices tend to increase as the departure date approaches, with flights booked 0-6 days out averaging $775. Even booking more than 60 days in advance saw slightly higher average prices at $474.

Across the trailing quarter, a good price for a flight from Denver to Chicago is considered to be $273 or less. The median price for this route was $386. Fares can go higher, with 75% of prices observed being $585 or less. Travelers aiming for the most economical options should target prices at or below the $273 threshold.

Historically, March has been the cheapest month to fly from Denver to Chicago, with a median price of $243. February also offered competitive fares, with a median price of $265. While September had a median price of $352, it was also identified as the most expensive month, indicating price variability. The annual median price for this route was $386.

Related routes

More routes from Denver

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Flights to Chicago from other cities

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Denver to Chicago: Overview

Insights for flights from Denver to Chicago

How much is a round trip from Denver to Chicago

Regular price: $72 - $194

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

The regular price range for flights from Denver to Chicago is $72 to $194. The current lowest deal is $164 with Frontier Airlines, for travel from Feb 6-Feb 24.

now $164

Low $72

High $194

The cheapest time to fly from Denver to Chicago

March

Cheapest

Flights from $243

April

Most Expensive

Flights from $1,537

Jan

Feb

Mar

Apr

May

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Denver to Chicago

Frontier Airlines

Last-minute flights going from Denver to Chicago

Wed, Oct 21

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$226

$183

One-way

Fri, Oct 23

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$124

$94

One-way

Fri, Oct 23

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$225

$178

One-way

Sat, Oct 24

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$123

$79

One-way

Mon, Oct 26

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$122

$76

One-way

Tue, Oct 27

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$120

$42

One-way

Biggest price drops on these dates for flights from Denver to Chicago

7 nights

Nov 10 - Nov 17

$102 → $40

61%

5 nights

Nov 19 - Nov 24

$199 → $139

30%

3 nights

Nov 21 - Nov 24

$204 → $149

27%

14 nights

Nov 4 - Nov 18

$89 → $40

55%

Popular Airports to fly from Denver to Chicago

Denver - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Denver to Chicago are above the typical level, with a median price of $386.

📅 Best time to fly

Cheapest months: March, February, September

Historically, the cheapest months to fly from Denver to Chicago are March ($243), February ($265), and September ($352).

⏱️ Flight duration

Nonstop flights average 5h 26m

Nonstop flights from Denver to Chicago typically take 5h 26m, while connecting flights average 21h 33m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 66.6% of recent routes, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines provides direct flights on this route, with recent deals as low as $164.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Denver to Chicago are frequently available, especially within a 30-day window.

Denver main airports to depart from

Denver International (DEN)

Cheapest

Denver International Airport is a convenient choice for flights from Denver to Chicago.

📍 ~30 km from city center (reachable by car)

💸 Flights from ~$147

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering a wide range of flights to Chicago.

📍 ~25 km from Chicago city center (reachable by public transport, taxi, car rental).

💸 Flights from ~$40

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 car or train)

💸 Flights from ~$297

Business & First Class Flight Deals to Chicago

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

Elite

Best Elite deals to Chicago

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

From DEN

Elite

Oct 28

Chicago, United States

80% AI deal score

$1,429

$524

Save $905

From DEN

Elite

Oct 27

Chicago, United States

78% AI deal score

$1,193

$469

Save $724

From DEN

Elite

Dec 07

Chicago, United States

76% AI deal score

$2,195

$1,265

Save $930

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Oct 19

Chicago, United States

75% AI deal score

$1,271

$684

Save $587

From DEN

Elite

Dec 15

Chicago, United States

72% AI deal score

$1,986

$1,193

Save $793

From DEN

Elite

Dec 15

Chicago, United States

72% AI deal score

$1,986

$1,193

Save $793

From DEN

Elite

Dec 14

Chicago, United States

72% AI deal score

$1,986

$1,203

Save $783

From DEN

Elite

Dec 14

Chicago, United States

72% AI deal score

$1,986

$1,203

Save $783

From DEN

Elite

Oct 14

Chicago, United States

72% AI deal score

$1,685

$1,179

Save $506

From DEN

Elite

Dec 07

Chicago, United States

70% AI deal score

$1,987

$1,395

Save $592

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Dec 07

Chicago, United States

70% AI deal score

$2,044

$1,430

Save $614

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Nov 15

Chicago, United States

69% AI deal score

$1,852

$1,451

Save $401

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Denver to Chicago

Today’s best flight deals from Denver to Chicago

Denver to Chicago: Overview

Insights for flights from Denver to Chicago

How much is a round trip from Denver to Chicago

The cheapest time to fly from Denver to Chicago

Direct flights from Denver to Chicago

Last-minute flights going from Denver to Chicago

Biggest price drops on these dates for flights from Denver to Chicago

Popular Airports to fly from Denver to Chicago

Denver - Chicago route insights

Recent fares are above the typical level

Cheapest months: March, February, September

Nonstop flights average 5h 26m

Connecting flights are dominant

Frontier Airlines offers direct flights

Deals are frequent on this route

Denver main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Oct 28

Oct 27

Dec 07

Oct 19

Dec 15

Dec 15

Dec 14

Dec 14

Oct 14

Dec 07

Dec 07

Nov 15

Frequently Asked Questions About Flights to Chicago

When is the best time to book flights from Denver to Chicago?

What's a cheap fare from Denver to Chicago?

What's the cheapest month to fly from Denver to Chicago?

Are there direct flights from Denver to Chicago?

How long is the flight from Denver to Chicago?

Are there frequently good prices on flights from Denver to Chicago?

Related routes

More routes from Denver

Flights to Chicago from other cities

Denver to Chicago: Overview

Insights for flights from Denver to Chicago

How much is a round trip from Denver to Chicago

The cheapest time to fly from Denver to Chicago

Direct flights from Denver to Chicago

Last-minute flights going from Denver to Chicago

Biggest price drops on these dates for flights from Denver to Chicago

Popular Airports to fly from Denver to Chicago

Denver - Chicago route insights

Recent fares are above the typical level

Cheapest months: March, February, September

Nonstop flights average 5h 26m

Connecting flights are dominant

Frontier Airlines offers direct flights

Deals are frequent on this route

Denver main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Oct 28

Oct 27

Dec 07

Oct 19

Dec 15

Dec 15

Dec 14

Dec 14

Oct 14

Dec 07

Dec 07

Nov 15

Frequently Asked Questions About Flights to Chicago

When is the best time to book flights from Denver to Chicago?

What's a cheap fare from Denver to Chicago?

What's the cheapest month to fly from Denver to Chicago?