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$63+ Cheap flights from Colorado 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Colorado to Chicago

Keep the following information in mind while searching for Colorado to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$116
(CheapOair)

One-way from

$63
(Kiwi.com)

Popular in

May

Cheapest in

October

Average price

$195

Good round-trip deal

$165 or less

Good one-way deal

$115 or less
From Colorado to Chicago (CHI)
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One-way flight from Colorado to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Colorado to Chicago (CHI).
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Price to beat on a one-way flight from Colorado to Chicago (CHI).
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Find flight deals from Colorado to Chicago

Cheapest flights from Colorado to Chicago
Explore the most affordable flight options available from Colorado to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This CheapOair deal was found by Cheapflights users on 9/13. 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 10/109:19 pmDEN - ORD
Nonstop2h 40mFrontier
Fri 10/176:42 pmORD - DEN
1 stop6h 30mFrontier
Deal found 9/13$116
This CheapOair deal was found by Cheapflights users on 9/13. 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.
Mon 10/277:49 amDEN - MDW
Nonstop2h 27mFrontier
Fri 10/311:37 pmMDW - DEN
1 stop8h 53mFrontier
Deal found 9/13$116
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Sat 9/275:50 pmDEN - ORD
Nonstop2h 38mFrontier
Tue 9/307:20 amORD - DEN
Nonstop2h 53mFrontier
Deal found 9/13$117
This CheapOair deal was found by Cheapflights users on 9/14. 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
Sun 11/96:30 amMDW - DEN
1 stop26h 06mFrontier
Deal found 9/14$117
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/78:22 pmDEN - ORD
Nonstop2h 31mFrontier
Tue 10/147:15 amORD - DEN
Nonstop2h 49mFrontier
Deal found 9/15$118
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/712:36 amDEN - ORD
1 stop13h 32mFrontier
Tue 10/147:15 amORD - DEN
Nonstop2h 49mFrontier
Deal found 9/13$119
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:05 amDEN - MDW
Nonstop2h 25mFrontier
Sun 11/1612:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/14$119
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/118:22 pmDEN - ORD
Nonstop2h 31mFrontier
Sun 10/125:50 amORD - DEN
1 stop20h 01mFrontier
Deal found 9/14$120
This CheapOair deal was found by Cheapflights users on 9/14. 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 11/78:05 amDEN - MDW
Nonstop2h 25mFrontier
Fri 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/14$120
This Frontier deal was found by Cheapflights users on 9/14. 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.
Wed 10/15:50 pmDEN - ORD
Nonstop2h 38mFrontier
Fri 10/310:42 amORD - DEN
Nonstop2h 51mFrontier
Deal found 9/14$122
This Frontier deal was found by Cheapflights users on 9/13. 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.
Wed 10/2212:36 amDEN - MDW
1 stop8h 11mFrontier
Fri 10/3112:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/13$122
This Frontier deal was found by Cheapflights users on 9/14. 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.
Wed 10/15:50 pmDEN - ORD
Nonstop2h 38mFrontier
Thu 10/22:07 pmORD - DEN
1 stop8h 05mFrontier
Deal found 9/14$123

Cheapflights Fare Finder

 
Customize your flight search to find flights from Colorado 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 September 15, 2025.
Use the filters below to find and compare flights from Colorado to Chicago that are best for you.

Fly from

Colorado

Fly to

Chicago

Route

Depart

Return

Price

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 11/4

10:15 am-5:15 pm

1 stop6h 00m

Chicago Midway

Thu 11/6

9:40 pm-11:15 pm

Nonstop2h 35m

$152

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 12/3

6:00 am-9:40 am

Nonstop2h 40m

Chicago O'Hare Intl

Mon 12/8

8:07 pm-9:56 pm

Nonstop2h 49m

$157

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 10/16

4:45 pm-8:25 pm

Nonstop2h 40m

Chicago O'Hare Intl

Mon 10/20

9:44 pm-11:30 pm

Nonstop2h 46m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 10/18

8:15 am-11:40 am

Nonstop2h 25m

Chicago Midway

Mon 10/20

9:50 pm-11:25 pm

Nonstop2h 35m

$157

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

Sat 10/11

3:40 pm-9:30 pm

1 stop4h 50m

Chicago O'Hare Intl

Sat 10/18

9:10 am-11:15 am

Nonstop3h 05m

$165

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 10/7

1:30 pm-7:25 pm

1 stop4h 55m

Chicago Midway

Sat 10/11

12:20 pm-2:00 pm

Nonstop2h 40m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 10/7

7:55 am-12:40 pm

1 stop3h 45m

Chicago Midway

Tue 10/7

8:40 pm-10:20 pm

Nonstop2h 40m

$167

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/29

5:30 pm-10:40 pm

1 stop4h 10m

Chicago Midway

Sat 11/1

6:00 pm-7:35 pm

Nonstop2h 35m

$167

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 10/7

6:00 am-3:20 pm

2 stops8h 20m

Chicago O'Hare Intl

Tue 10/7

6:55 pm-8:55 pm

Nonstop3h 00m

$172

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 11/13

8:45 pm-12:05 am

Nonstop2h 20m

Chicago Midway

Sun 11/16

7:45 am-9:25 am

Nonstop2h 40m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
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Best time to book a flight from Colorado to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Colorado 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 Colorado to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Colorado to Chicago (average of $245). Flying from Colorado 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 CO to CHI?

Find hourly flight availability from Colorado 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 September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Colorado to Chicago as you normally would.

Weekly flight availability from Colorado to Chicago

Explore weekly flight availability from Colorado 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 September 15, 2025.

The most flights from USCO to CHI are scheduled on a Friday (77 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (42 on average).

Related info for your journey

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

  • How long is the flight from Colorado to Chicago?

    Departing from Colorado to Chicago will take you 2h 40m. The distance from Colorado to Chicago is about 886 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The most popular route from Colorado to Chicago is Denver Intl - Chicago O'Hare Intl. You may also consider Denver Intl - Chicago Midway or Colorado Springs - Chicago O'Hare Intl.

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

    Consider Cathay Pacific (85%), Japan Airlines (84%) or Turkish Airlines (77%) when booking your flight. These represent the most reliable airlines when flying from Colorado to Chicago.

  • What are the cheapest flights from Colorado to Chicago?

    The cheapest flight price from Colorado to Chicago is $61. On average you can expect to pay $1,041. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $77.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Colorado 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 Colorado to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Colorado to Chicago (average of $245). Flying from Colorado 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 Colorado 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 Colorado to Chicago

Discover the top 4 airlines that operate flights from Colorado 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$165FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$152Average$295FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$388FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$165Average$445FlexibilityNo cancel feeOn-time69%

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