Are there direct flights from Denver to Chicago?

Yes, direct flights are available from Denver to Chicago. Historically, approximately 50.2% of flights on this route have been direct. For flights that include stopovers, travelers typically experience a median of 2 stopovers in the trailing 90 days.

How long is the flight from Denver to Chicago?

The typical direct flight from Denver to Chicago has a duration of 2 hours and 39 minutes, covering a distance of 1437 kilometers. Flights with one stopover, however, tend to be considerably longer. Historically, these flights have a median duration of 10 hours and 26 minutes.

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 classified as one with consistent deal availability. Travelers can often find competitive fares when planning their trips, based on observations over a 30-day period.

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 6 days ago

451 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 17, 2026.)

Today’s best flight deals from Denver to Chicago

Explore current cheapest deals departing from Denver to Chicago

2026-09-15 – 2026-09-29
DEN - Chicago
76% AI deal score
$112
$67
Round trip
2026-10-03 – 2026-10-28
DEN - Chicago
72% AI deal score
$91
$67
Round trip
2026-09-10 – 2026-09-14
DEN - Chicago
78% AI deal score
$139
$68
Round trip
2026-09-12 – 2026-09-14
DEN - Chicago
78% AI deal score
$139
$68
Round trip
2026-10-15 – 2026-10-28
DEN - Chicago
73% AI deal score
$101
$70
Round trip
2026-11-11 – 2026-11-14
DEN - Chicago
75% AI deal score
$114
$70
Round trip
2026-11-03 – 2026-11-10
DEN - Chicago
74% AI deal score
$107
$70
Round trip
2026-09-19 – 2026-09-29
DEN - Chicago
75% AI deal score
$116
$70
Round trip
2026-10-28 – 2026-11-14
DEN - Chicago
72% AI deal score
$99
$70
Round trip
2026-10-28 – 2026-11-10
DEN - Chicago
73% AI deal score
$101
$70
Round trip

Denver to Chicago: Overview

Insights for flights from Denver to Chicago

A typical journey from Denver to Chicago takes 2h 39m, including itineraries with connections. While a meaningful share of flights are non-stop, about half of all itineraries involve at least one stop. For those connecting, the median number of stopovers is 2.

For travelers seeking cheap flights from Denver to Chicago, prices typically range from $157–$468, with a median of $289. Right now, current fares are near the typical level. Approximately 7% of recent fares from Denver to Chicago were classified as a good price, and new deals appear almost daily.

When is the cheapest time to fly from Denver to Chicago? The most affordable month to fly is typically August, with a median fare of $103. Following closely, November also offers competitive prices, with a median fare of $104. December is another relatively inexpensive option, with a median fare of $121.

The route from Denver to Chicago covers a distance of 1437 km. This falls into the short-haul category, indicating a relatively quick trip between the two cities.

How much is a round trip from Denver to Chicago

Regular price: $86 - $204

Prices are currently below the regular range.

The regular price range for flights from Denver to Chicago is $86 to $204. The current lowest deal is $67 with Frontier Airlines, for travel from Sep 15-Sep 29.

now $67

Low $86

High $204

The cheapest time to fly from Denver to Chicago

The cheapest month to fly from Denver to Chicago is January, with a median price of $123. The most expensive month is June, with a median price of $377. Prices are generally lower from January to December.

January

Cheapest

Flights from $123

June

Most Expensive

Flights from $377

Jan

Feb

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Denver to Chicago

Frontier Airlines

Last-minute flights going from Denver to Chicago

Mon, Aug 17

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$562

$300

One-way

Mon, Aug 17

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$549

$312

One-way

Wed, Aug 19

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$482

$282

One-way

Wed, Aug 19

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$546

$290

One-way

Thu, Aug 20

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$539

$302

One-way

Sat, Aug 22

⌛ Last-Minute

DEN - Chicago

Denver (DEN) - Chicago (ORD)

Frontier Airlines

$539

$282

One-way

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

3 nights

Aug 22 - Aug 25

$527 → $417

21%

2 nights

Aug 23 - Aug 25

$498 → $412

17%

4 nights

Aug 19 - Aug 23

$565 → $505

11%

3 nights

Sep 26 - Sep 29

$136 → $86

37%

Popular Airports to fly from Denver to Chicago

Denver - Chicago route insights

💸 Price insights

Recent fares are near the typical level.

Recent fares from Denver to Chicago are near the typical level, with 7% good prices.

📅 Best time to fly

Fly in August for deals around $103.

Historically, August, November, and December offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights average 2h 39m.

The median flight time for direct routes is 2h 39m, while connecting flights average 14h 41m.

✈️ Airlines & availability

Mixed availability of direct and connecting flights.

Approximately 50.2% of recent flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers direct flights.

Frontier Airlines has direct flight options available for the Denver to Chicago route.

🎯 Booking tip

Deals are frequent on this route.

Deals on flights from Denver to Chicago are frequent, appearing within a 30-day window.

Denver main airports to depart from

Denver International (DEN)

Cheapest

Denver International Airport is a convenient departure point for flights to Chicago.

📍 ~30 km from Denver (reachable by car or train)

💸 Flights from ~$60

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering many connections from Denver.

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

💸 Flights from ~$60

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 ~$303

Business & First Class Flight Deals to Chicago

78% AI deal score

$2,140

$1,184

Save $956

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Oct 27

Chicago, United States

78% AI deal score

$2,137

$1,185

Save $952

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Oct 29

Chicago, United States

78% AI deal score

$2,171

$1,188

Save $983

Alaska Airlines, Inc.

Business Class

From DEN

Elite

Oct 26

Chicago, United States

78% AI deal score

$2,137

$1,188

Save $949

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal time to book flights from Denver to Chicago is 60+ days out. Prices for this booking window average around $216. Booking within 14-27 days of departure typically sees an average price of $231. Conversely, waiting until 0-6 days before departure can result in significantly higher average prices, around $586.

Across the trailing quarter, a good price for a flight from Denver to Chicago is considered to be $157 or less. The median price for this route has been $289. Fares can go up to $468 or more, representing the higher end of prices observed over a 90-day period.

Historically, August has been the cheapest month to fly from Denver to Chicago, with a median price of $103. November also offers competitive prices, with a median of $104. December, while still relatively inexpensive compared to the annual median of $289, has a median price of $121.

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

The route from Denver to Chicago covers a distance of 1437 km. This falls into the short-haul category, indicating a relatively quick trip between the two cities.

How much is a round trip from Denver to Chicago

Regular price: $86 - $204

Prices are currently below the regular range.

The regular price range for flights from Denver to Chicago is $86 to $204. The current lowest deal is $67 with Frontier Airlines, for travel from Sep 15-Sep 29.

now $67

Low $86

High $204

The cheapest time to fly from Denver to Chicago

January

Cheapest

Flights from $123

June

Most Expensive

Flights from $377

Jan

Feb

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec