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Pueblo

$68+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pueblo are usually found in January or October, booked 35 days in advance, depart on a Wednesday or Saturday and return on a Thursday

Cheap 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 December 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Wed 12/317:00 amORD - DEN
Nonstop2h 56mFrontier
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/25$173
This Expedia deal was found by Cheapflights users on 12/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amORD - DEN
Nonstop2h 56mFrontier
Mon 1/57:00 amDEN - ORD
1 stop26h 49mFrontier
Deal found 12/25$234
This Super.com deal was found by Cheapflights users on 12/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amORD - DEN
Nonstop2h 56mFrontier
Thu 1/18:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/25$242
This Frontier deal was found by Cheapflights users on 12/25. 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.
Tue 12/307:00 amORD - DEN
Nonstop2h 56mFrontier
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/25$259
This CheapOair deal was found by Cheapflights users on 12/25. 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.
Wed 12/317:00 amORD - DEN
Nonstop2h 56mFrontier
Sun 1/49:00 pmDEN - ORD
1 stop25h 54mFrontier
Deal found 12/25$269
This CheapOair deal was found by Cheapflights users on 12/25. 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 12/265:45 amORD - DEN
1 stop9h 30mFrontier
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/25$281
This CheapOair deal was found by Cheapflights users on 12/24. 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.
Wed 12/317:00 amORD - DEN
Nonstop2h 56mFrontier
Tue 1/611:59 pmDEN - ORD
1 stop15h 20mFrontier
Deal found 12/24$284
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Sun 12/286:10 amORD - DEN
1 stop16h 39mFrontier
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/25$292
This CheapOair deal was found by Cheapflights users on 12/25. 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.
Tue 12/302:01 pmMDW - DEN
Nonstop2h 45mFrontier
Thu 1/811:59 pmDEN - MDW
1 stop22h 10mFrontier
Deal found 12/25$292
This Cheapflightsfares deal was found by Cheapflights users on 12/25. 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.
Mon 12/297:00 amORD - DEN
Nonstop2h 56mFrontier
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 12/25$293
This Super.com deal was found by Cheapflights users on 12/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - DEN
1 stop8h 54mFrontier
Wed 1/710:29 pmDEN - MDW
1 stop12h 16mFrontier
Deal found 12/26$323
This CheapOair deal was found by Cheapflights users on 12/26. 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 12/292:16 pmMDW - DEN
1 stop19h 11mFrontier
Thu 1/811:59 pmDEN - MDW
1 stop22h 10mFrontier
Deal found 12/26$324

Find flight deals from Chicago to Pueblo

Keep the following information in mind while searching for Chicago to Pueblo flight deals. Data was last updated December 27, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$112
(Cheapflightsfares)

One-way from

$68
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$275
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. 7% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 27, 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

Fri 2/27

2:35 pm-4:44 pm

Nonstop3h 09m

Denver Intl

Mon 3/2

11:59 pm-3:52 pm

1 stop14h 53m

$124

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Fri 1/30

12:07 pm-2:05 pm

Nonstop2h 58m

Denver Intl

Mon 2/2

3:06 pm-11:47 am

1 stop19h 41m

$142

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 2/14

2:40 pm-4:36 pm

Nonstop2h 56m

Denver Intl

Wed 2/18

7:24 pm-10:53 pm

Nonstop2h 29m

$157

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sun 1/11

10:07 pm-11:58 pm

Nonstop2h 51m

Denver Intl

Thu 1/15

5:41 pm-9:24 pm

Nonstop2h 43m

$168

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 2/11

1:55 pm-3:52 pm

Nonstop2h 57m

Denver Intl

Tue 2/17

7:45 am-11:19 am

Nonstop2h 34m

$179

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Thu 1/8

7:50 pm-9:49 pm

Nonstop2h 59m

Denver Intl

Fri 1/9

7:26 pm-10:56 pm

Nonstop2h 30m

$182

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 2/11

2:15 pm-9:05 pm

1 stop7h 50m

Denver Intl

Sat 2/14

10:25 am-2:05 pm

Nonstop2h 40m

$186

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 2/10

10:05 am-11:50 am

Nonstop2h 45m

Denver Intl

Fri 2/13

7:55 pm-11:10 pm

Nonstop2h 15m

$188

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Fri 1/30

7:00 am-8:49 am

Nonstop2h 49m

Denver Intl

Tue 2/3

4:15 pm-7:51 pm

Nonstop2h 36m

$188

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Thu 1/15

6:20 am-12:21 pm

1 stop7h 01m

Denver Intl

Tue 1/20

7:30 am-11:46 pm

2 stops15h 16m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 44 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 December 19, 2025.

The best time to book flights from Chicago to Pueblo is 35 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, November is the cheapest month in which you can book a flight from Chicago to Pueblo (average of $139). Flying from Chicago to Pueblo in July is currently the most expensive (average of $311). 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 December 27, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 48% on flights from Chicago to Pueblo by exploring options for tickets in the afternoon.

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 December 27, 2025.

The most flights from CHI to PU5 are scheduled on a Monday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Chicago to Pueblo?

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 December 27, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Pueblo have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,114 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,066 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,071 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago to Pueblo?

    For as low as $188, Frontier can have you in Pueblo from Chicago in 2h 45m. There are 893 mi between Chicago and Pueblo. Most flights are nonstop.

  • 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 $38. However, be on the lookout for offers from Southwest and American 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 (62%), SkyWest Airlines (60%), American Airlines (59%).

  • What are the cheapest flights from Chicago to Pueblo?

    Looking at all options, your cheapest flight can be booked for $93. While the most popular route (Chicago O'Hare Intl - Denver Intl) can be booked for $112 on average, our data indicates $352 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, November is the cheapest month in which you can book a flight from Chicago to Pueblo (average of $139). Flying from Chicago to Pueblo in July is currently the most expensive (average of $311). 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

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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 December 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$163Average$346FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$241Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$271Average$394FlexibilityNo cancel feeOn-time69%

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