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$44+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Dec 29 — Jan 51
Sun 12/29
Sun 1/5
1 adult, Economy
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1. Tell us where you want to go
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The best prices from Denver Intl to Chicago are usually found in April or May, booked 61 days in advance, depart on a Wednesday or Saturday and return on a Saturday

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 December 24, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$81
(Trip.com)

One-way from

$44
(CheapOair)

Popular in

December

Cheapest in

April

Average price

$242
Provider with most accurate pricing for Denver Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Denver Intl-Chicago (CHI) flights.
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From Denver Intl to Chicago (CHI)
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One-way flight from Denver Intl to Chicago (CHI)
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High demand for flights, 13% potential price rise
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Best time to find cheap flights, 4% potential price drop
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Average for round-trip flights in December 2024
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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 December 24, 2024.

This Frontier deal was found by Cheapflights users on 12/23. 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.
Mon 12/3011:04 pmDEN - MDW
1 stop15h 09mFrontier
Mon 1/610:04 pmMDW - DEN
Nonstop2h 53mFrontier
Deal found 12/23$168
This Cheapflightsfares deal was found by Cheapflights users on 12/23. 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.
Tue 12/319:47 amDEN - ORD
Nonstop2h 33mFrontier
Wed 1/16:00 amORD - DEN
Nonstop2h 57mFrontier
Deal found 12/23$214
This CheapOair deal was found by Cheapflights users on 12/23. 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.
Tue 12/319:47 amDEN - ORD
Nonstop2h 33mMultiple Airlines
Sun 1/58:03 pmORD - DEN
1 stop22h 27mMultiple Airlines
Deal found 12/23$283
This American Airlines deal was found by Cheapflights users on 12/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/313:30 pmDEN - ORD
Nonstop2h 28mAmerican Airlines
Wed 1/19:19 pmORD - DEN
Nonstop2h 48mAmerican Airlines
Deal found 12/23$311
This Sun Country Air deal was found by Cheapflights users on 12/23. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3110:04 amDEN - ORD
1 stop6h 34mSun Country Air
Sun 1/58:03 pmORD - DEN
1 stop22h 27mSun Country Air
Deal found 12/23$328
This Southwest deal was found by Cheapflights users on 12/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:20 pmDEN - MDW
Nonstop2h 20mSouthwest
Sun 1/510:40 pmMDW - DEN
Nonstop2h 40mSouthwest
Deal found 12/23$336
This Southwest deal was found by Cheapflights users on 12/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:05 pmDEN - ORD
Nonstop2h 30mSouthwest
Sun 1/57:30 amORD - DEN
2 stops6h 40mSouthwest
Deal found 12/23$354
This Delta deal was found by Cheapflights users on 12/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3012:20 amDEN - MDW
1 stop7h 30mDelta
Sun 1/59:30 amMDW - DEN
1 stop5h 24mDelta
Deal found 12/23$368
This Delta deal was found by Cheapflights users on 12/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3012:20 amDEN - ORD
1 stop8h 01mDelta
Wed 1/17:00 amORD - DEN
1 stop8h 10mDelta
Deal found 12/23$442
This United Airlines deal was found by Cheapflights users on 12/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/286:00 pmDEN - ORD
Nonstop2h 30mUnited Airlines
Tue 1/288:05 pmORD - DEN
Nonstop2h 53mUnited Airlines
Deal found 12/24$445

Find flights from Denver to Chicago within your budget

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 December 24, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 1/9

8:55 pm-12:13 am

Nonstop2h 18m

Chicago Midway

Mon 1/13

7:15 am-9:05 am

Nonstop2h 50m

$81

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 3/12

9:08 pm-12:44 am

Nonstop2h 36m

Chicago O'Hare Intl

Wed 3/19

6:45 am-8:48 am

Nonstop3h 03m

$82

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 2/4

5:55 pm-9:25 pm

Nonstop2h 30m

Chicago O'Hare Intl

Tue 2/11

5:50 pm-7:40 pm

Nonstop2h 50m

$139

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 2/1

6:10 pm-9:30 pm

Nonstop2h 20m

Chicago Midway

Tue 2/4

8:35 pm-10:25 pm

Nonstop2h 50m

$140

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 1/15

8:07 am-11:45 am

Nonstop2h 38m

Chicago O'Hare Intl

Sat 1/18

5:35 pm-7:16 pm

Nonstop2h 41m

$159

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 2/15

6:20 am-10:00 am

Nonstop2h 40m

Chicago O'Hare Intl

Sun 2/16

7:45 pm-9:40 pm

Nonstop2h 55m

$169

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sun 1/5

7:15 pm-6:05 pm

1 stop21h 50m

Chicago O'Hare Intl

Sun 1/12

7:25 am-9:26 am

Nonstop3h 01m

$191

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 1/9

2:21 pm-9:58 pm

1 stop6h 37m

Chicago O'Hare Intl

Wed 1/15

10:30 am-5:43 pm

1 stop8h 13m

$216

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 1/15

7:10 am-4:21 pm

1 stop8h 11m

Chicago Midway

Tue 1/21

1:26 pm-8:25 pm

1 stop7h 59m

$216

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 6/19

12:16 pm-7:11 pm

1 stop5h 55m

Chicago O'Hare Intl

Sun 6/22

8:10 pm-9:19 am

1 stop14h 09m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 26 results
1
2
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Compare providers for flights from Denver to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Denver to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Denver-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Denver-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Denver-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Denver-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Denver-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Denver to Chicago flights

Find out what our experts recommend to make the most of your Denver to Chicago trip
Airlines
Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for added comfort.


Consider early check-in to secure your place on overbooked flights.

Read more about Frontierby Marisa Garcia
United Airlines

United's Economy Plus offers extra legroom, enhancing comfort on domestic flights.


United Club lounges provide healthy snacks and comfortable seating for a relaxing wait.

Read more about United Airlinesby Harriet Baskas
American Airlines

American Airlines offers Main Cabin Extra seats with more legroom for added comfort.


Access Admirals Club Lounges for a relaxing pre-flight experience with refreshments and entertainment.

Read more about American Airlinesby Marisa Garcia
Airports
DEN

Parking at DEN is extensive. For budget options, use the Pikes Peak Lot or Longs Peak Lot, both under 10 minutes by shuttle.

Read more about DENby Emily Zemler
ORD

For a quick city transfer from ORD, use the 'L' train. It's often faster than taxis due to traffic.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line train is the easiest way to reach downtown Chicago from MDW, taking less than 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and American Airlines

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

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.

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.

Travel insights for flights from Denver to Chicago

Get recent, data-driven insights about flights from Denver to Chicago including ideal travel times, pricing trends, and more.

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 December 20, 2024.

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 61 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 $317). 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 December 24, 2024.

It’s optimal to fly from Denver to Chicago in the evening. By choosing this option you can save up to 27% 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 December 16, 2024.

Travelers seeking maximum savings on their Denver to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday 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 December 24, 2024.

The most flights from DEN to CHI are scheduled on a Monday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 December 24, 2024.
Read through reviews of airlines operating flights from Denver to Chicago, such as United Airlines, American Airlines and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,765 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,765 reviews
Southwest
8.1
Very good
4,765 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,555 reviews
Southwest
8.1
Very good
4,765 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,580 reviews
Southwest
8.1
Very good
4,765 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,260 reviews
Southwest
8.1
Very good
4,765 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,009 reviews
Southwest
8.1
Very good
4,765 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 46 outbound flights to Chicago per day from 4 airlines. Denver Intl is conveniently located just 18.5 mi from Denver’s city center.

  • 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 $81. Additional round-trip tickets that might be worth considering are offered by United Airlines and Southwest, with the lowest prices starting at $139 and $140, respectively. You may be able to fly from Denver to Chicago for 50% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Denver to Chicago one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $44. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Denver to Chicago for a low price.

  • 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 (94%), Copa Airlines (94%) and Cathay Pacific (93%).

  • What are the cheapest flights from Denver to Chicago?

    Looking at all options, your cheapest flight can be booked for $84. While the most popular route (Denver Intl - Chicago O'Hare Intl) can be booked for $103 on average our data indicates $1,387 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 $317). 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

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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.
Denver to O'Hare Intl flights
Denver to Midway flights
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Colorado Springs to Bloomington flights
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Colorado Springs to Moline flights
Denver to Rockford flights
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Durango to Moline flights
Montrose to Springfield flights
Montrose to Peoria flights
Colorado Springs to Springfield flights
Colorado Springs to Peoria flights
Vail to Midway flights
Colorado Springs to Champaign flights
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Durango to Midway flights
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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 December 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$132FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$232FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$142Average$306FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$143Average$242FlexibilityNo cancel feeOn-time63%
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