Pueblo

$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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — COS
Jul 7 — Jul 141
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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 Friday or Wednesday 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 July 2, 2025.

Round-trip from

$128
(Frontier)

One-way from

$78
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$197
From Chicago (CHI) to Pueblo
One-way flight from Chicago (CHI) to Pueblo
High demand for flights, 0% potential price rise
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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 July 2, 2025.

This Priceline deal was found by Cheapflights users on 7/2. 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.
Wed 7/307:00 amORD - DEN
Nonstop2h 53mFrontier
Tue 8/512:59 amDEN - ORD
1 stop8h 26mFrontier
Deal found 7/2$126
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:40 amMDW - DEN
1 stop7h 47mFrontier
Mon 8/188:15 amDEN - MDW
Nonstop2h 26mFrontier
Deal found 7/2$128
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Wed 8/67:10 amORD - DEN
Nonstop2h 41mAmerican Airlines
Wed 8/132:05 pmDEN - ORD
Nonstop2h 39mAmerican Airlines
Deal found 6/30$157
This Southwest deal was found by Cheapflights users on 6/30. 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 7/305:25 pmMDW - DEN
Nonstop2h 50mSouthwest
Mon 8/49:55 amDEN - MDW
Nonstop2h 25mSouthwest
Deal found 6/30$167
This Southwest deal was found by Cheapflights users on 6/30. 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 8/207:30 amORD - DEN
2 stops8h 30mSouthwest
Mon 8/2510:35 amDEN - ORD
Nonstop2h 30mSouthwest
Deal found 6/30$172

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 July 2, 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 7/30

7:00 am-8:53 am

Nonstop2h 53m

Denver Intl

Tue 8/5

12:59 am-10:25 am

1 stop8h 26m

$126

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 8/14

7:40 am-2:27 pm

1 stop7h 47m

Denver Intl

Mon 8/18

8:15 am-11:41 am

Nonstop2h 26m

$128

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 8/6

7:10 am-8:51 am

Nonstop2h 41m

Denver Intl

Wed 8/13

2:05 pm-5:44 pm

Nonstop2h 39m

$157

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 7/30

5:25 pm-7:15 pm

Nonstop2h 50m

Denver Intl

Mon 8/4

9:55 am-1:20 pm

Nonstop2h 25m

$167

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 8/20

7:30 am-3:00 pm

2 stops8h 30m

Denver Intl

Mon 8/25

10:35 am-2:05 pm

Nonstop2h 30m

$172

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Fri 10/31

12:47 pm-9:49 pm

1 stop10h 02m

$78

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Mon 8/18

5:00 am-6:43 am

Nonstop2h 43m

$79

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 8/27

8:20 am-9:55 am

Nonstop2h 35m

$79

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Mon 8/11

4:01 pm-11:48 pm

1 stop8h 47m

$82

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 11/5

1:45 pm-10:40 pm

1 stop9h 55m

$94

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 14 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 27, 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 July 2, 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 July 2, 2025.

The most flights from CHI to PU5 are scheduled on a Monday (8 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (3 on average).

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 July 2, 2025.
See what other customers who have flown with Southwest, Delta, and United 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.

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
8.0
Very good

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $78. 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: United Airlines (84%), SkyWest Airlines (82%), American Airlines (82%).

  • What are the cheapest flights from Chicago to Pueblo?

    Looking at all options, your cheapest flight can be booked for $71. While the most popular route (Chicago O'Hare Intl - Denver Intl) can be booked for $97 on average our data indicates $310 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.

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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$251Average$331FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$267Average$421FlexibilityNo cancel feeOn-time69%

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