HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pueblo

$64+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Pueblo with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 Tuesday 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 April 24, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$116
(Cheapflightsfares)

One-way from

$64
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$195
Provider with most accurate pricing for Chicago (CHI)-Denver Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Denver Intl flights.
Search Deals
From Chicago (CHI) to Pueblo
Search Deals
One-way flight from Chicago (CHI) to Pueblo
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 April 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Thu 5/296:00 amORD - DEN
Nonstop3h 02mFrontier
Fri 5/308:22 pmDEN - ORD
Nonstop2h 30mFrontier
Deal found 4/23$116
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Sat 5/242:44 pmMDW - DEN
Nonstop2h 49mFrontier
Sat 5/315:26 pmDEN - MDW
Nonstop2h 27mFrontier
Deal found 4/23$141
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/217:10 amORD - DEN
Nonstop2h 56mUnited Airlines
Wed 5/284:17 pmDEN - ORD
Nonstop2h 43mUnited Airlines
Deal found 4/23$151
This Southwest deal was found by Cheapflights users on 4/23. 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.
Wed 5/145:50 amMDW - DEN
Nonstop2h 35mSouthwest
Mon 5/199:05 pmDEN - MDW
Nonstop2h 25mSouthwest
Deal found 4/23$160
This Southwest deal was found by Cheapflights users on 4/23. 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.
Wed 5/217:00 amORD - DEN
Nonstop2h 40mSouthwest
Wed 5/288:35 amDEN - ORD
1 stop5h 25mSouthwest
Deal found 4/23$161
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 5/179:45 pmORD - DEN
Nonstop2h 48mAmerican Airlines
Wed 5/211:45 pmDEN - ORD
Nonstop2h 46mAmerican Airlines
Deal found 4/22$165
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 6/73:45 pmORD - DEN
1 stop5h 13mDelta
Sun 6/812:59 amDEN - ORD
1 stop8h 10mDelta
Deal found 4/23$217
This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 6/71:55 pmMDW - DEN
1 stop7h 03mDelta
Fri 6/1312:59 amDEN - MDW
1 stop7h 42mDelta
Deal found 4/22$217
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Fri 7/255:40 amORD - DEN
Nonstop2h 50mMultiple Airlines
Sun 7/277:00 amDEN - ORD
1 stop9h 15mMultiple Airlines
Deal found 4/23$222
This Sun Country Air deal was found by Cheapflights users on 4/23. 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.
Sun 7/202:30 pmORD - DEN
1 stop19h 15mSun Country Air
Sun 7/277:00 amDEN - ORD
1 stop9h 15mSun Country Air
Deal found 4/23$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 April 24, 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

Thu 5/29

6:00 am-8:02 am

Nonstop3h 02m

Denver Intl

Fri 5/30

8:22 pm-11:52 pm

Nonstop2h 30m

$116

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 5/24

2:44 pm-4:33 pm

Nonstop2h 49m

Denver Intl

Sat 5/31

5:26 pm-8:53 pm

Nonstop2h 27m

$141

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 5/21

7:10 am-9:06 am

Nonstop2h 56m

Denver Intl

Wed 5/28

4:17 pm-8:00 pm

Nonstop2h 43m

$151

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 5/14

5:50 am-7:25 am

Nonstop2h 35m

Denver Intl

Mon 5/19

9:05 pm-12:30 am

Nonstop2h 25m

$160

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 5/21

7:00 am-8:40 am

Nonstop2h 40m

Denver Intl

Wed 5/28

8:35 am-3:00 pm

1 stop5h 25m

$161

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 5/17

9:45 pm-11:33 pm

Nonstop2h 48m

Denver Intl

Tue 5/20

7:00 am-10:32 am

Nonstop2h 32m

$165

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 6/7

3:45 pm-7:58 pm

1 stop5h 13m

Denver Intl

Sun 6/8

12:59 am-10:09 am

1 stop8h 10m

$217

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 6/7

1:55 pm-7:58 pm

1 stop7h 03m

Denver Intl

Fri 6/13

12:59 am-9:41 am

1 stop7h 42m

$217

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 7/19

7:00 am-8:53 am

Nonstop2h 53m

Denver Intl

Sun 7/27

7:00 am-5:15 pm

1 stop9h 15m

$225

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 6/28

6:10 am-4:07 pm

1 stop10h 57m

Denver Intl

Sun 6/29

6:15 am-7:17 pm

1 stop12h 02m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 24 results
1
2
3

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 April 18, 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 $437). 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 April 24, 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 April 24, 2025.

The most flights from CHI to PU5 are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 April 24, 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
9,918 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $64. 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 (76%), United Airlines (76%), Emirates (69%).

  • What are the cheapest flights from Chicago to Pueblo?

    Looking at all options, your cheapest flight can be booked for $157. While the most popular route (Chicago O'Hare Intl - Denver Intl) can be booked for $124 on average our data indicates $272 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 $437). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Pueblo

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Denver flights
St. Louis to Denver flights
Midway to Denver flights
O'Hare Intl to Colorado Springs flights
Peoria to Denver flights
Moline to Denver flights
O'Hare Intl to Montrose flights
O'Hare Intl to Aspen flights
O'Hare Intl to Grand Junction flights
Midway to Colorado Springs flights
Evansville to Denver flights
Bloomington to Denver flights
O'Hare Intl to Vail flights
O'Hare Intl to Durango flights
St. Louis to Durango flights
O'Hare Intl to Hayden flights
Midway to Aspen flights
St. Louis to Colorado Springs flights
Midway to Grand Junction flights
Dubuque to Denver flights
Peoria to Colorado Springs flights
St. Louis to Vail flights
O'Hare Intl to Gunnison flights
Decatur to Denver flights
Springfield to Denver flights
St. Louis to Aspen flights
St. Louis to Montrose flights
Moline to Colorado Springs flights
Bloomington to Colorado Springs flights
Champaign to Denver flights
Evansville to Colorado Springs flights
St. Louis to Grand Junction flights
St. Louis to Gunnison flights
Moline to Vail flights
Peoria to Grand Junction flights
Springfield to Colorado Springs flights
Paducah to Colorado Springs flights
Moline to Grand Junction flights
Bloomington to Montrose flights
O'Hare Intl to Cortez flights
St. Louis to Cortez flights
Evansville to Vail flights
Moline to Montrose flights
Marion to Denver flights
Evansville to Grand Junction flights
Peoria to Montrose flights
Champaign to Colorado Springs flights

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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$227Average$320FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$262Average$408FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$346FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.