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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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pueblo are usually found in November or October, booked 30 days in advance, depart on a Wednesday or Saturday 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 September 15, 2025.

Round-trip from

$98
(CheapOair)

One-way from

$64
(United Airlines)

Popular in

December

Cheapest in

November

Average price

$181
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, 1% 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 September 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 September 15, 2025.

This CheapOair deal was found by Cheapflights users on 9/13. 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.
Sat 10/48:25 amORD - DEN
Nonstop2h 51mFrontier
Tue 10/78:22 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 9/13$98
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 12/87:39 pmORD - DEN
Nonstop2h 59mFrontier
Sat 12/132:59 pmDEN - ORD
Nonstop2h 35mFrontier
Deal found 9/13$102
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 11/712:30 pmMDW - DEN
Nonstop2h 46mFrontier
Fri 11/148:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 9/15$103
This Frontier deal was found by Cheapflights users on 9/14. 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.
Fri 10/2412:11 pmMDW - DEN
Nonstop2h 46mFrontier
Sat 10/2512:25 pmDEN - MDW
1 stop9h 22mFrontier
Deal found 9/14$104
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/25:35 amORD - DEN
Nonstop2h 45mFrontier
Sat 10/118:22 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 9/13$105
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Fri 10/316:00 amORD - DEN
Nonstop2h 41mFrontier
Sun 11/28:41 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 9/13$106
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Fri 10/246:50 amORD - DEN
Nonstop2h 41mFrontier
Sun 10/266:00 amDEN - ORD
Nonstop2h 36mFrontier
Deal found 9/13$107
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Fri 10/2410:51 amORD - DEN
Nonstop2h 47mFrontier
Sat 11/18:41 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 9/14$108
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/17:20 amORD - DEN
Nonstop2h 53mFrontier
Wed 10/88:22 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 9/14$109
This CheapOair deal was found by Cheapflights users on 9/14. 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 10/106:24 pmMDW - DEN
Nonstop2h 44mFrontier
Mon 10/136:05 amDEN - MDW
Nonstop2h 26mFrontier
Deal found 9/14$109
This Frontier deal was found by Cheapflights users on 9/14. 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 9/307:20 amORD - DEN
Nonstop2h 53mFrontier
Sun 10/56:00 amDEN - ORD
Nonstop2h 37mFrontier
Deal found 9/14$110
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 11/612:30 pmMDW - DEN
Nonstop2h 46mFrontier
Sun 11/98:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 9/15$110

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 September 15, 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

MDW - DEN

MDWDEN

Chicago Midway

Sat 12/13

5:15 pm-6:55 pm

Nonstop2h 40m

Denver Intl

Mon 12/15

2:35 pm-7:20 pm

1 stop3h 45m

$152

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 10/11

5:15 am-6:55 am

Nonstop2h 40m

Denver Intl

Sat 10/18

5:40 am-9:00 am

Nonstop2h 20m

$157

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 10/28

8:40 pm-10:20 pm

Nonstop2h 40m

Denver Intl

Mon 11/3

8:00 am-1:55 pm

1 stop4h 55m

$167

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 11/20

9:50 am-2:25 pm

1 stop5h 35m

Denver Intl

Sat 11/22

8:25 pm-11:45 pm

Nonstop2h 20m

$167

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 2/28

5:15 pm-7:05 pm

Nonstop2h 50m

Denver Intl

Tue 3/3

6:45 am-1:00 pm

1 stop5h 15m

$167

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Fri 12/12

9:40 pm-11:15 pm

Nonstop2h 35m

Denver Intl

Mon 12/15

10:15 am-5:00 pm

1 stop5h 45m

$171

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 1/24

6:15 pm-8:13 pm

Nonstop2h 58m

Denver Intl

Fri 1/30

5:42 pm-9:15 pm

Nonstop2h 33m

$179

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 1/14

1:45 pm-9:20 pm

2 stops8h 35m

Denver Intl

Wed 1/21

6:45 am-1:00 pm

1 stop5h 15m

$182

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Fri 10/24

7:05 pm-11:35 pm

1 stop5h 30m

Denver Intl

Sat 11/1

12:10 pm-7:05 pm

2 stops5h 55m

$197

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Fri 2/6

1:00 pm-9:30 pm

1 stop9h 30m

Denver Intl

Tue 2/10

6:45 am-1:00 pm

1 stop5h 15m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 41 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 September 12, 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 March is currently the most expensive (average of $412). 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 September 15, 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 September 15, 2025.

The most flights from CHI to PU5 are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 September 15, 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
4,242 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $152, Southwest can have you in Pueblo from Chicago in 2h 40m. There are 893 mi between Chicago and Pueblo. Most flights are nonstop.

  • 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 (71%), American Airlines (57%), SkyWest Airlines (55%).

  • What are the cheapest flights from Chicago to Pueblo?

    Looking at all options, your cheapest flight can be booked for $136. While the most popular route (Chicago O'Hare Intl - Denver Intl) can be booked for $77 on average, our data indicates $292 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 March is currently the most expensive (average of $412). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$244Average$353FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$248Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$271Average$417FlexibilityNo cancel feeOn-time69%

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