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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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Pueblo are usually found in November or September, booked 30 days in advance, depart on a Wednesday or Saturday and return on a Thursday

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 November 6, 2025.

This Frontier deal was found by Cheapflights users on 11/4. 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.
Mon 11/247:00 amORD - DEN
Nonstop3h 00mFrontier
Thu 11/278:45 pmDEN - ORD
Nonstop2h 25mFrontier
Deal found 11/4$95
This CheapOair deal was found by Cheapflights users on 11/6. 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 11/1712:30 pmMDW - DEN
Nonstop2h 46mFrontier
Thu 11/207:15 amDEN - MDW
1 stop14h 02mFrontier
Deal found 11/6$95
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/47:00 amORD - DEN
Nonstop2h 56mFrontier
Sun 12/148:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 11/4$96
This Super.com deal was found by Cheapflights users on 11/6. 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.
Fri 11/217:00 amORD - DEN
Nonstop3h 00mFrontier
Sun 11/238:45 pmDEN - ORD
Nonstop2h 25mFrontier
Deal found 11/6$97
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/58:42 pmMDW - DEN
1 stop13h 20mFrontier
Sun 12/77:45 amDEN - MDW
Nonstop2h 23mFrontier
Deal found 11/6$97
This Expedia deal was found by Cheapflights users on 11/5. 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.
Fri 12/56:00 amORD - DEN
1 stop15h 25mFrontier
Mon 12/88:45 pmDEN - ORD
Nonstop2h 27mFrontier
Deal found 11/5$98
This Frontier deal was found by Cheapflights users on 11/4. 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 12/57:00 amORD - DEN
Nonstop2h 56mFrontier
Tue 12/912:59 amDEN - ORD
1 stop12h 32mFrontier
Deal found 11/4$99
This Frontier deal was found by Cheapflights users on 11/4. 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 12/512:18 pmMDW - DEN
Nonstop2h 44mFrontier
Fri 12/512:59 amDEN - MDW
1 stop12h 00mFrontier
Deal found 11/4$99
This Frontier deal was found by Cheapflights users on 11/4. 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 11/216:00 amORD - DEN
1 stop6h 51mFrontier
Mon 11/248:45 pmDEN - ORD
Nonstop2h 25mFrontier
Deal found 11/4$101
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 12/812:18 pmMDW - DEN
Nonstop2h 44mFrontier
Fri 12/121:42 pmDEN - MDW
1 stop7h 30mFrontier
Deal found 11/6$101
This Booking.com deal was found by Cheapflights users on 11/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:00 amORD - DEN
Nonstop2h 56mFrontier
Sun 12/79:00 pmDEN - ORD
1 stop25h 57mFrontier
Deal found 11/5$102
This Super.com deal was found by Cheapflights users on 11/6. 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.
Thu 11/203:37 pmORD - DEN
1 stop10h 04mFrontier
Sun 11/238:45 pmDEN - ORD
Nonstop2h 25mFrontier
Deal found 11/6$103

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 November 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$94
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$163
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
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 6, 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 1/8

1:55 pm-3:52 pm

Nonstop2h 57m

Denver Intl

Thu 1/15

7:50 am-11:34 am

Nonstop2h 44m

$133

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Tue 1/20

1:45 pm-7:20 pm

1 stop6h 35m

Denver Intl

Tue 1/27

1:45 pm-10:35 pm

1 stop7h 50m

$153

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 1/29

6:00 am-7:50 am

Nonstop2h 50m

Denver Intl

Mon 2/2

6:25 pm-9:50 pm

Nonstop2h 25m

$155

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 12/3

7:10 am-8:55 am

Nonstop2h 45m

Denver Intl

Sun 12/7

6:00 am-9:40 am

Nonstop2h 40m

$165

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 12/11

7:05 am-8:45 am

Nonstop2h 40m

Denver Intl

Tue 12/16

8:00 am-11:25 am

Nonstop2h 25m

$177

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sun 12/7

7:45 am-9:25 am

Nonstop2h 40m

Denver Intl

Wed 12/10

4:45 pm-8:05 pm

Nonstop2h 20m

$177

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 1/31

9:45 am-1:50 pm

1 stop5h 05m

Denver Intl

Mon 2/9

7:05 pm-10:25 pm

Nonstop2h 20m

$186

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 2/26

5:15 am-10:25 am

1 stop6h 10m

Denver Intl

Sun 3/1

5:15 am-8:45 am

Nonstop2h 30m

$188

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 2/12

1:35 pm-5:45 pm

1 stop5h 10m

Denver Intl

Tue 2/17

7:35 am-11:10 am

Nonstop2h 35m

$188

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 1/7

1:45 pm-9:05 pm

2 stops8h 20m

Denver Intl

Sat 1/10

5:50 am-1:30 pm

1 stop6h 40m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 45 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 October 31, 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, February is the cheapest month in which you can book a flight from Chicago to Pueblo (average of $159). 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 November 6, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 53% on flights from Chicago to Pueblo by exploring options for tickets in the morning.

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 November 6, 2025.

The most flights from CHI to PU5 are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 November 6, 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
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

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
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

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
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

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
3,116 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

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 $133, United Airlines can have you in Pueblo from Chicago in 2h 57m. There are 886 mi between Chicago and Pueblo. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Pueblo one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $77. However, be on the lookout for offers from United Airlines and Delta, 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 (82%), SkyWest Airlines (81%), Lufthansa (72%).

  • What are the cheapest flights from Chicago to Pueblo?

    Looking at all options, your cheapest flight can be booked for $125. While the most popular route (Chicago O'Hare Intl - Denver Intl) can be booked for $78 on average, our data indicates $259 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, February is the cheapest month in which you can book a flight from Chicago to Pueblo (average of $159). 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

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$163Average$328FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$248Average$382FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$272Average$401FlexibilityNo cancel feeOn-time69%

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