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$43+ Cheap flights from Chicago (CHI) to Pueblo, CO

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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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The best prices from Chicago to Pueblo are usually found in May or April, booked 30 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap flight deals from Chicago to Pueblo

Keep the following information in mind while searching for Chicago to Pueblo flight deals. Data was last updated febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$73
(Frontier)

One-way from

$44
(Cheapflightsfares)

Popular in

December

Cheapest in

May

Average price

$191
Provider with most accurate pricing for Chicago (CHI)-Denver Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Denver Intl flights.
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From Chicago (CHI) to Pueblo
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One-way flight from Chicago (CHI) to Pueblo
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Highest demand for flights based on searches. 7% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Chicago to Pueblo

Cheapest flights from Chicago to Pueblo
Explore the most affordable flight options available from Chicago to Pueblo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/66:40 amMDW - DEN
Nonstop2h 52mFrontier
lun. 3/108:55 pmDEN - MDW
Nonstop2h 22mFrontier
Deal found 2/20$71
This Frontier deal was found by Cheapflights users on 2/20. 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.
vie. 3/76:30 amORD - DEN
Nonstop3h 03mFrontier
lun. 3/109:08 pmDEN - ORD
Nonstop2h 36mFrontier
Deal found 2/20$73
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/3112:10 pmORD - DEN
1 stop7h 43mMultiple Airlines
mié. 4/29:08 pmDEN - ORD
Nonstop2h 34mMultiple Airlines
Deal found 2/19$144
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/18:40 pmORD - DEN
Nonstop2h 53mAmerican Airlines
mié. 4/95:26 pmDEN - ORD
Nonstop2h 34mAmerican Airlines
Deal found 2/20$159
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/2610:05 amMDW - DEN
1 stop4h 25mSouthwest
mié. 4/27:45 pmDEN - MDW
Nonstop2h 20mSouthwest
Deal found 2/19$170
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/107:10 pmORD - DEN
Nonstop2h 50mSouthwest
mar. 3/185:55 amDEN - ORD
1 stop5h 50mSouthwest
Deal found 2/20$179
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/110:25 amORD - DEN
1 stop7h 51mDelta
vie. 4/412:55 amDEN - ORD
1 stop7h 17mDelta
Deal found 2/19$217
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/11:16 pmMDW - DEN
1 stop7h 42mDelta
mié. 4/166:20 amDEN - MDW
1 stop5h 15mDelta
Deal found 2/20$217

Find flights from Chicago to Pueblo within your budget

Customize your flight search to find flights from Chicago to Pueblo 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 febrero 20, 2025.

Fly from

Chicago

Fly to

Pueblo

Route

Depart

Return

Price

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

jue. 3/6

6:40 am-8:32 am

Nonstop2h 52m

Denver Intl

lun. 3/10

8:55 pm-12:17 am

Nonstop2h 22m

$71

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

vie. 3/7

6:30 am-8:33 am

Nonstop3h 03m

Denver Intl

lun. 3/10

9:08 pm-12:44 am

Nonstop2h 36m

$73

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

lun. 3/31

12:10 pm-6:53 pm

1 stop7h 43m

Denver Intl

mié. 4/2

9:08 pm-12:42 am

Nonstop2h 34m

$144

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

mar. 4/1

8:40 pm-10:33 pm

Nonstop2h 53m

Denver Intl

mié. 4/9

5:26 pm-9:00 pm

Nonstop2h 34m

$159

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

mié. 3/26

10:05 am-1:30 pm

1 stop4h 25m

Denver Intl

mié. 4/2

7:45 pm-11:05 pm

Nonstop2h 20m

$170

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

lun. 3/10

7:10 pm-9:00 pm

Nonstop2h 50m

Denver Intl

mar. 3/18

5:55 am-12:45 pm

1 stop5h 50m

$179

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

mar. 4/1

9:34 am-1:57 pm

1 stop5h 23m

Denver Intl

lun. 4/7

12:55 am-8:34 am

1 stop6h 39m

$217

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

mar. 4/1

1:16 pm-7:58 pm

1 stop7h 42m

Denver Intl

mié. 4/16

6:20 am-12:35 pm

1 stop5h 15m

$217

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

vie. 2/28

6:45 pm-9:01 pm

1 stop27h 16m

Denver Intl

sáb. 3/8

8:00 am-7:30 am

1 stop22h 30m

$225

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

sáb. 3/15

8:04 pm-10:00 pm

Nonstop2h 56m

Denver Intl

lun. 3/17

8:55 pm-12:23 am

Nonstop2h 28m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 24 results
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Best time to book a flight from Chicago to Pueblo

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

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Pueblo. Price data was last updated on February 14, 2025.

The best time to book flights from Chicago to Pueblo is 30 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Pueblo (average of $316). Flying from Chicago to Pueblo in June is currently the most expensive (average of $443). 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 CHI to PU5?

Find hourly flight availability from Chicago to Pueblo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 20, 2025.

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

Rainfall in Pueblo by month

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

In terms of precipitation, rainfall in Pueblo ranges from 0.5 - 2.3 inches per month. May is typically the wettest month, when rainfall can reach 2.3 in. January is typically the driest time to visit Pueblo when rainfall is around 0.5 in.

Temperature in Pueblo by month

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

If weather is an important factor for your trip to Pueblo, 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 30.2 F).

Reviews of airlines servicing Pueblo

Get insights into the airlines that provide service to Pueblo. 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 Pueblo. Reviews last updated febrero 20, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta from Chicago to Pueblo by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Pueblo. 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 Chicago to Pueblo 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 United Airlines and Southwest, as they are both options that can get you from Chicago to Pueblo for a low price.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Pueblo on time: SkyWest Airlines (69%), United Airlines (69%), Emirates (47%).

  • What are the cheapest flights from Chicago to Pueblo?

    Looking at all options, your cheapest flight can be booked for $190. While the most popular route (Chicago O'Hare Intl - Denver Intl) can be booked for $111 on average our data indicates $341 when flying from Chicago to Pueblo.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Pueblo (average of $316). Flying from Chicago to Pueblo in June is currently the most expensive (average of $443). 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 Chicago to Pueblo

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Pueblo

Discover the top 3 airlines that operate flights from Chicago to Pueblo. 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$205Average$321FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$412FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$270Average$356FlexibilityNo cancel feeOn-time63%
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