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$78+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pueblo are usually found in September or November, booked 30 days in advance, depart on a Wednesday 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 June 12, 2025.

Round-trip from

$136
(Cheapflightsfares)

One-way from

$78
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$216
From Chicago (CHI) to Pueblo
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One-way flight from Chicago (CHI) to Pueblo
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High demand for flights, 0% potential price rise
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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 June 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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Wed 7/167:00 amORD - DEN
Nonstop2h 53mFrontier
Mon 7/218:31 pmDEN - ORD
Nonstop2h 39mFrontier
Deal found 6/10$136
This Priceline deal was found by Cheapflights users on 6/12. 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.
Sat 8/92:44 pmMDW - DEN
Nonstop2h 49mFrontier
Mon 8/118:15 amDEN - MDW
Nonstop2h 26mFrontier
Deal found 6/12$140
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 8/278:50 pmMDW - DEN
Nonstop2h 35mSouthwest
Tue 9/25:50 amDEN - MDW
Nonstop2h 20mSouthwest
Deal found 6/10$157
This Southwest deal was found by Cheapflights users on 6/10. 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 8/57:00 amORD - DEN
Nonstop2h 40mSouthwest
Sat 8/99:35 amDEN - ORD
Nonstop2h 30mSouthwest
Deal found 6/10$158
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 10/37:00 amORD - DEN
Nonstop2h 36mAmerican Airlines
Mon 10/67:27 amDEN - ORD
Nonstop2h 32mAmerican Airlines
Deal found 6/11$175
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 7/155:20 pmORD - DEN
1 stop6h 46mDelta
Sat 7/196:35 amDEN - ORD
1 stop7h 28mDelta
Deal found 6/10$217
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 7/156:20 pmMDW - DEN
1 stop5h 46mDelta
Mon 7/2112:55 amDEN - MDW
1 stop6h 49mDelta
Deal found 6/10$217
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 7/46:35 pmORD - DEN
Nonstop3h 01mUnited Airlines
Mon 7/78:55 pmDEN - ORD
Nonstop2h 35mUnited Airlines
Deal found 6/11$260
This Sun Country Air deal was found by Cheapflights users on 6/10. 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.
Wed 7/912:30 pmORD - DEN
1 stop21h 53mSun Country Air
Fri 7/185:49 pmDEN - ORD
1 stop22h 26mSun Country Air
Deal found 6/10$265

Cheapflights Fare Finder

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 June 12, 2025.
Use the filters below to find and compare flights from Chicago to Pueblo that are best for you.

Fly from

Chicago

Fly to

Pueblo

Route

Depart

Return

Price

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 7/16

7:00 am-8:53 am

Nonstop2h 53m

Denver Intl

Mon 7/21

8:31 pm-12:10 am

Nonstop2h 39m

$136

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 8/9

2:44 pm-4:33 pm

Nonstop2h 49m

Denver Intl

Mon 8/11

8:15 am-11:41 am

Nonstop2h 26m

$140

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 8/27

8:50 pm-10:25 pm

Nonstop2h 35m

Denver Intl

Tue 9/2

5:50 am-9:10 am

Nonstop2h 20m

$157

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Tue 8/5

7:00 am-8:40 am

Nonstop2h 40m

Denver Intl

Sat 8/9

9:35 am-1:05 pm

Nonstop2h 30m

$158

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Tue 8/5

6:48 am-8:22 am

Nonstop2h 34m

Denver Intl

Sat 8/9

5:32 pm-9:18 pm

Nonstop2h 46m

$168

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Tue 7/15

5:20 pm-11:06 pm

1 stop6h 46m

Denver Intl

Mon 7/21

12:55 am-7:49 am

1 stop5h 54m

$217

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 7/15

6:20 pm-11:06 pm

1 stop5h 46m

Denver Intl

Mon 7/21

12:55 am-8:44 am

1 stop6h 49m

$217

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Fri 7/4

6:35 pm-8:36 pm

Nonstop3h 01m

Denver Intl

Mon 7/7

8:55 pm-12:30 am

Nonstop2h 35m

$260

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 6/25

11:50 am-8:07 pm

1 stop9h 17m

Denver Intl

Thu 6/26

8:21 pm-11:59 pm

Nonstop2h 38m

$264

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 7/9

12:30 pm-9:23 am

1 stop21h 53m

Denver Intl

Fri 7/18

5:49 pm-5:15 pm

1 stop22h 26m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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.

Cheapflights Insights

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

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 June 9, 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 $413). 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 June 12, 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.

Weekly flight availability from Chicago to Pueblo

Explore weekly flight availability from Chicago to Pueblo. 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 June 12, 2025.

The most flights from CHI to PU5 are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

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 June 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
725 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 American Airlines, with whom users have recently found tickets for as low as $78. However, be on the lookout for offers from Southwest and United Airlines, 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: United Airlines (87%), SkyWest Airlines (86%), Emirates (75%).

  • What are the cheapest flights from Chicago to Pueblo?

    Looking at all options, your cheapest flight can be booked for $155. While the most popular route (Chicago O'Hare Intl - Denver Intl) can be booked for $130 on average our data indicates $526 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 $413). 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$251Average$333FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$266Average$421FlexibilityNo cancel feeOn-time69%

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