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$78+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$130
(FlightHub)

One-way from

$77
(Orbitz)

Popular in

May

Cheapest in

September

Average price

$221

Good round-trip deal

$158 or less

Good one-way deal

$106 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. 11% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/275:50 pmDEN - ORD
Nonstop2h 52mFrontier
sáb. 8/307:00 amORD - DEN
Nonstop2h 53mFrontier
Deal found 7/30$130
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
jue. 10/167:10 pmDEN - MDW
Nonstop2h 28mFrontier
vie. 10/174:29 pmMDW - DEN
Nonstop2h 48mFrontier
Deal found 7/29$131
This Southwest deal was found by Cheapflights users on 7/29. 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.
sáb. 9/137:25 pmDEN - MDW
Nonstop2h 25mSouthwest
mié. 9/178:50 pmMDW - DEN
Nonstop2h 35mSouthwest
Deal found 7/29$157
This Southwest deal was found by Cheapflights users on 7/29. 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.
mar. 8/267:30 pmDEN - ORD
Nonstop2h 35mSouthwest
mié. 8/2712:40 pmORD - DEN
Nonstop2h 40mSouthwest
Deal found 7/29$161
This American Airlines deal was found by Cheapflights users on 7/30. 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.
sáb. 8/305:32 pmDEN - ORD
Nonstop2h 46mAmerican Airlines
dom. 8/3111:50 amORD - DEN
Nonstop2h 35mAmerican Airlines
Deal found 7/30$168
This American Airlines deal was found by Cheapflights users on 7/29. 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.
vie. 9/512:14 pmASE - ORD
Nonstop2h 58mAmerican Airlines
dom. 9/79:31 amORD - ASE
Nonstop3h 10mAmerican Airlines
Deal found 7/29$191
This United Airlines deal was found by Cheapflights users on 7/29. 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.
vie. 9/56:15 pmASE - ORD
1 stop4h 44mUnited Airlines
dom. 9/77:15 amORD - ASE
1 stop4h 35mUnited Airlines
Deal found 7/29$211
This Southwest deal was found by Cheapflights users on 7/30. 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.
mié. 9/1011:55 amCOS - MDW
Nonstop2h 20mSouthwest
sáb. 9/205:35 pmMDW - COS
Nonstop2h 30mSouthwest
Deal found 7/30$217
This American Airlines deal was found by Cheapflights users on 7/31. 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.
sáb. 9/612:25 pmCOS - ORD
Nonstop2h 45mAmerican Airlines
mar. 9/99:56 amORD - COS
Nonstop2h 55mAmerican Airlines
Deal found 7/31$217
This United Airlines deal was found by Cheapflights users on 7/31. 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.
lun. 8/2512:02 pmCOS - ORD
Nonstop2h 41mUnited Airlines
mar. 8/265:00 amORD - COS
1 stop5h 04mUnited Airlines
Deal found 7/31$227
This Delta deal was found by Cheapflights users on 7/28. 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.
mié. 9/108:00 amCOS - ORD
1 stop8h 30mDelta
sáb. 9/133:45 pmORD - COS
1 stop5h 54mDelta
Deal found 7/28$237
This American Airlines deal was found by Cheapflights users on 7/28. 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.
mié. 9/244:59 pmDRO - ORD
1 stop6h 00mAmerican Airlines
mié. 10/13:08 pmORD - DRO
1 stop5h 51mAmerican Airlines
Deal found 7/28$238

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 julio 31, 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 - ORD

DENORD

Denver Intl

mié. 8/27

5:50 pm-9:42 pm

Nonstop2h 52m

Chicago O'Hare Intl

sáb. 8/30

7:00 am-8:53 am

Nonstop2h 53m

$130

DenverChicago

DEN - MDW

DENMDW

Denver Intl

jue. 10/16

7:10 pm-10:38 pm

Nonstop2h 28m

Chicago Midway

vie. 10/17

4:29 pm-6:17 pm

Nonstop2h 48m

$131

DenverChicago

DEN - MDW

DENMDW

Denver Intl

sáb. 9/13

8:00 am-11:25 am

Nonstop2h 25m

Chicago Midway

mar. 9/16

8:20 am-9:55 am

Nonstop2h 35m

$157

DenverChicago

DEN - ORD

DENORD

Denver Intl

mar. 8/26

7:30 pm-11:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

mié. 8/27

12:40 pm-2:20 pm

Nonstop2h 40m

$161

DenverChicago

DEN - ORD

DENORD

Denver Intl

sáb. 8/30

12:04 pm-3:47 pm

Nonstop2h 43m

Chicago O'Hare Intl

dom. 8/31

7:10 am-8:51 am

Nonstop2h 41m

$168

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

vie. 9/5

12:14 pm-4:12 pm

Nonstop2h 58m

Chicago O'Hare Intl

dom. 9/7

9:31 am-11:41 am

Nonstop3h 10m

$191

AspenChicago

ASE - ORD

ASEORD

Aspen Pitkin County

vie. 9/5

6:15 pm-11:59 pm

1 stop4h 44m

Chicago O'Hare Intl

dom. 9/7

7:15 am-10:50 am

1 stop4h 35m

$211

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

mié. 9/10

11:55 am-3:15 pm

Nonstop2h 20m

Chicago Midway

sáb. 9/20

5:35 pm-7:05 pm

Nonstop2h 30m

$217

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

sáb. 9/6

12:25 pm-4:10 pm

Nonstop2h 45m

Chicago O'Hare Intl

mar. 9/9

9:56 am-11:51 am

Nonstop2h 55m

$217

Colorado SpringsChicago

COS - ORD

COSORD

Colorado Springs

lun. 8/25

12:02 pm-3:43 pm

Nonstop2h 41m

Chicago O'Hare Intl

mar. 8/26

5:00 am-9:04 am

1 stop5h 04m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 59 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 julio 31, 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 julio 31, 2025.

The most flights from USCO to CHI are scheduled on a Thursday (81 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (42 on average).

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 julio 31, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Colorado to Chicago have to say. 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    One-way options have recently been found by users for as low as $77 on Frontier. Other airlines that offer cheap prices include United Airlines from $79 and Southwest from $79 one-way.

  • 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 Japan Airlines (88%), Turkish Airlines (88%) or Copa Airlines (87%) 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 $78. On average you can expect to pay $1,131. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $99.

  • 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
Valparaiso
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 5 airlines flying from Colorado to Chicago

Discover the top 5 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$56Average$156FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$151Average$386FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$154Average$292FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$162Average$441FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$216FlexibilityNo cancel feeOn-timeN/A

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