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$60+ Cheap flights from Denver (DEN) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Aug 27 — Sep 31
Wed 8/27
Wed 9/3
1 adult, Economy
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Cheapflights Tip: The best prices from Denver Intl to Chicago are usually found in October or September, booked 69 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Denver to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Denver (DEN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 22, 2025.

Round-trip from

$115
(CheapOair)

One-way from

$60
(Flightnetwork)

Popular in

May

Cheapest in

October

Average price

$181

Good round-trip deal

$166 or less

Good one-way deal

$126 or less
From Denver Intl to Chicago (CHI)
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One-way flight from Denver Intl to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Denver Intl to Chicago (CHI).
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Price to beat on a one-way flight from Denver Intl to Chicago (CHI).
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Find flight deals from Denver to Chicago

Cheapest flights from Denver to Chicago
Explore the most affordable flight options available from Denver to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2025.

This Priceline deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:50 pmDEN - ORD
Nonstop2h 38mFrontier
Sat 9/1312:22 pmORD - DEN
1 stop7h 40mFrontier
Deal found 8/21$115
This Mytrip deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/51:12 pmDEN - MDW
1 stop9h 08mFrontier
Mon 9/84:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/21$115
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:50 pmDEN - ORD
Nonstop2h 38mFrontier
Mon 9/157:40 amORD - DEN
1 stop12h 27mFrontier
Deal found 8/21$116
This Mytrip deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1212:28 pmDEN - MDW
Nonstop2h 25mFrontier
Mon 9/154:48 pmMDW - DEN
Nonstop2h 38mFrontier
Deal found 8/20$116
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:44 pmDEN - ORD
Nonstop2h 31mFrontier
Sun 11/91:36 pmORD - DEN
1 stop19h 00mFrontier
Deal found 8/21$117
This Cheapflightsfares deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:15 pmDEN - MDW
Nonstop2h 21mFrontier
Mon 12/152:45 pmMDW - DEN
Nonstop2h 45mFrontier
Deal found 8/19$117
This Cheapflightsfares deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:44 pmDEN - ORD
Nonstop2h 31mFrontier
Fri 11/146:20 pmORD - DEN
1 stop6h 28mFrontier
Deal found 8/21$118
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/108:58 pmDEN - MDW
Nonstop2h 26mFrontier
Mon 10/1310:31 amMDW - DEN
Nonstop2h 41mFrontier
Deal found 8/21$118
This Priceline deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/51:12 pmDEN - ORD
1 stop9h 58mFrontier
Tue 9/97:20 amORD - DEN
Nonstop2h 53mFrontier
Deal found 8/21$119
This Priceline deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:15 pmDEN - MDW
Nonstop2h 21mFrontier
Sun 12/142:45 pmMDW - DEN
Nonstop2h 45mFrontier
Deal found 8/21$119
This Frontier deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:30 pmDEN - ORD
Nonstop2h 29mFrontier
Sun 9/146:00 amORD - DEN
Nonstop2h 45mFrontier
Deal found 8/20$120
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:05 amDEN - MDW
Nonstop2h 25mFrontier
Mon 11/101:37 pmMDW - DEN
1 stop8h 51mFrontier
Deal found 8/21$120

Cheapflights Fare Finder

 
Customize your flight search to find flights from Denver to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 22, 2025.
Use the filters below to find and compare flights from Denver to Chicago that are best for you.

Fly from

Denver

Fly to

Chicago

Route

Depart

Return

Price

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 10/15

8:10 pm-12:26 am

1 stop27h 16m

Chicago O'Hare Intl

Sat 10/18

7:05 am-8:54 am

Nonstop2h 49m

$115

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sun 9/14

12:59 am-10:31 am

1 stop8h 32m

Chicago O'Hare Intl

Wed 9/17

7:20 am-9:13 am

Nonstop2h 53m

$115

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 11/12

12:59 am-10:41 am

1 stop8h 42m

Chicago O'Hare Intl

Sat 11/15

7:15 am-9:04 am

Nonstop2h 49m

$115

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 9/16

5:50 pm-9:28 pm

Nonstop2h 38m

Chicago O'Hare Intl

Fri 9/19

4:03 pm-10:53 pm

1 stop7h 50m

$115

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 10/31

1:42 pm-12:11 am

1 stop9h 29m

Chicago O'Hare Intl

Sat 11/1

7:15 am-9:04 am

Nonstop2h 49m

$115

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sun 10/19

12:59 am-10:41 am

1 stop8h 42m

Chicago O'Hare Intl

Wed 10/22

7:15 am-9:04 am

Nonstop2h 49m

$115

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 9/18

6:00 am-9:37 am

Nonstop2h 37m

Chicago O'Hare Intl

Tue 9/30

7:20 am-9:13 am

Nonstop2h 53m

$115

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 9/20

5:50 pm-9:28 pm

Nonstop2h 38m

Chicago O'Hare Intl

Sat 9/27

12:22 pm-7:02 pm

1 stop7h 40m

$115

DenverChicago

DEN - ORD

DENORD

Denver Intl

Mon 9/29

7:40 am-10:45 pm

1 stop14h 05m

Chicago O'Hare Intl

Tue 9/30

7:20 am-9:13 am

Nonstop2h 53m

$115

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 9/5

1:12 pm-11:20 pm

1 stop9h 08m

Chicago Midway

Mon 9/8

4:48 pm-6:26 pm

Nonstop2h 38m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/21

Showing 1-10 of 52 results
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The best insider tips for Denver to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Denver to Chicago trip
Airlines
Frontier

Frontier's UpFront Plus offers a guaranteed empty middle seat for extra comfort.


Early check-in helps secure your place as Frontier often overbooks flights.

Read more about Frontierby Marisa Garcia
United Airlines

Basic Economy allows only a personal item; no carry-on bags unless exceptions apply.


United Club access includes healthy snacks and comfortable seating, but may be limited when full.

Read more about United Airlinesby Harriet Baskas
Airports
DEN

For a quick departure, use the A Line train to reach DEN from Union Station in 37 minutes, running every 15 minutes.

Read more about DENby Emily Zemler
ORD

For a smooth arrival at ORD, take the “L” train from the airport to downtown Chicago to avoid traffic delays.

Read more about ORDby Ramsey Qubein
MDW

Use the Orange Line train for a quick 30-minute ride from MDW to downtown Chicago, operating nearly 24 hours a day.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Emily Zemler

Emily Zemler

Expert on DEN

Emily Zemler

Emily Zemler

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more

Best time to book a flight from Denver to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Denver with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Denver to Chicago

How far ahead should I book a flight from Denver to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Denver to Chicago. Price data was last updated on August 8, 2025.

The price you pay for your flight from Denver to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 21 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Denver to Chicago?

Currently, August is the cheapest month in which you can book a flight from Denver to Chicago (average of $245). Flying from Denver to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DEN to CHI?

Find hourly flight availability from Denver to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 22, 2025.

It’s optimal to fly from Denver to Chicago in the evening. By choosing this option you can save up to 70% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Denver to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Denver to Chicago. Price data was last updated on August 17, 2025.

Travelers seeking maximum savings on their Denver to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Denver to Chicago

Explore weekly flight availability from Denver to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 22, 2025.

The most flights from DEN to CHI are scheduled on a Thursday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

How much does it cost to fly round-trip from Denver to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 22, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Denver to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,934 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,205 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Denver to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Denver to Chicago?

    Most people fly from Denver Intl (DEN) if they book a flight from Denver to Chicago. On average, Denver Intl has 56 outbound flights to Chicago per day from 4 airlines. Denver Intl is conveniently located just 18.5 mi from Denver’s city center.

  • How long is the flight from Denver to Chicago?

    Departing from Denver to Chicago will take you 27h 16m. There are 886 mi between Denver and Chicago.

  • What are the cheapest airlines flying from Denver to Chicago round-trip?

    Flying on Frontier is currently your cheapest option to Chicago, with prices starting at $57. Additional round-trip tickets that might be worth considering are offered by Southwest and American Airlines, with the lowest prices starting at $153 and $154, respectively. You may be able to fly from Denver to Chicago for 71% less than the average price by searching for these airlines.

  • What are the most popular routes from Denver to Chicago?

    When deciding which route to take from Denver to Chicago consider Denver Intl - Chicago O'Hare Intl, Denver Intl - Chicago Midway or Denver Intl - Chicago Greater Rockford as they are the most popular.

  • What are the most reliable airlines from Denver to Chicago?

    The top 3 most reliable airlines when flying from Denver to Chicago are Japan Airlines (80%), Cathay Pacific (80%) and Turkish Airlines (77%).

  • What are the cheapest flights from Denver to Chicago?

    Looking at all options, your cheapest flight can be booked for $63. While the most popular route (Denver Intl - Chicago O'Hare Intl) can be booked for $40 on average our data indicates $887 when flying from Denver to Chicago.

  • Can I find deals for flights from Denver to Chicago that include hotel bookings?

    Yes. In addition to deals on Denver to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Denver to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Denver to Chicago.

  • Can I find deals for business class flights from Denver to Chicago?

    Yes. Cheapflights offers flight deals from Denver to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Denver to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Denver to Chicago (average of $245). Flying from Denver to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Denver to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Denver to Chicago

Discover the top 4 airlines that operate flights from Denver to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$161FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$153Average$248FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$154Average$234FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$165Average$303FlexibilityNo cancel feeOn-time69%

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