$74 Cheap flight deals from Chicago (CHI) to Pueblo (COS)

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This Weekend's Flight Deals from Chicago to Pueblo

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Dec 12 - Sun, Dec 14
ORD
O'Hare Intl.
COS
Colorado Springs
$982 Roundtrip, found 1 day ago
$982
Roundtrip
found 1 day ago
Select United flight, departing Fri, Dec 12 from O'Hare Intl. to Colorado Springs, returning Sun, Dec 14, priced at $982 found 1 day ago

Airfares from $74 One Way, $186 Round Trip from Chicago to Pueblo

Prices starting at $186 for return flights and $74 for one-way flights to Pueblo were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Feb 14 - Tue, Feb 17
ORD
Chicago
COS
Colorado Springs
$186 Roundtrip, found 6 days ago
$186
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Feb 14 from Chicago to Colorado Springs, returning Tue, Feb 17, priced at $186 found 6 days ago
Fri, Jan 9 - Mon, Jan 12
ORD
Chicago
COS
Colorado Springs
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Select United flight, departing Fri, Jan 9 from Chicago to Colorado Springs, returning Mon, Jan 12, priced at $191 found 5 days ago
Sat, Feb 14 - Tue, Feb 17
ORD
Chicago
COS
Colorado Springs
$200 Roundtrip, found 6 days ago
$200
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Feb 14 from Chicago to Colorado Springs, returning Tue, Feb 17, priced at $200 found 6 days ago
Fri, Jan 9 - Mon, Jan 12
ORD
Chicago
COS
Colorado Springs
$205 Roundtrip, found 5 days ago
$205
Roundtrip
found 5 days ago
Select United flight, departing Fri, Jan 9 from Chicago to Colorado Springs, returning Mon, Jan 12, priced at $205 found 5 days ago
Fri, Jan 9 - Mon, Jan 12
ORD
Chicago
COS
Colorado Springs
$215 Roundtrip, found 5 days ago
$215
Roundtrip
found 5 days ago
Select United flight, departing Fri, Jan 9 from Chicago to Colorado Springs, returning Mon, Jan 12, priced at $215 found 5 days ago

Pueblo economy flight packages

Price found within the past 48 hours. Click for updated prices.
La Junta Colorado Cabins
3.0-star property

La Junta Colorado Cabins

8.6/10 Excellent! (41 reviews)

Jan 15 - Jan 18

3 night stay

Chicago (CHI) to Pueblo (PUB)

Frontier Airlines • Roundtrip • Coach
Price was $257, price is now $253 per person
$253
per person
found 19 hours ago
Clean cabin, pool was great for the kids, easy check-in! We'd definitely stay here again!

Reviewed on Aug 30, 2025

Royal Gorge Cabins
3.5-star property

Royal Gorge Cabins

9.6/10 Exceptional! (244 reviews)

Jan 15 - Jan 18

3 night stay

Chicago (CHI) to Pueblo (PUB)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $812, price is now $658 per person
$658
per person
found 19 hours ago
Cabin was roomy, clean and had an excellent layout. The Mountain View in the background was spectacular. We thoroughly enjoyed our stay there. The only thing that we didn’t like was the properties’ close proximity to Hwy 50. If you were sitting in the back porch in the evening you could hear cars. That’s only a minor issue and did not prevent us from enjoying our stay.

Reviewed on Jun 23, 2023

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More About Flying To Pueblo from Chicago

Route Information for Flights from Chicago to Pueblo

Origin Airport IATA Code
CHI
Destination Airport IATA Code
COS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Pueblo

Looking for guaranteed low prices on Chicago to Pueblo flights? Orbitz is your source and much more. From cutting-edge mobile tools to great deals, Orbitz makes it easy to book your dream vacation.

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Easily Plan Your Vacation

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Orbitz combines low prices on Chicago to Pueblo flights with discounts on quality hotels. Using Orbitz’s Display Matrix, you can see all your options and savings easily. With our low price guarantee, you know you have the best deals at your fingertips.

Frequently asked questions

Are there non-stop flights from Chicago to Pueblo?
Yes, there are two airlines that offer nonstop flights from Chicago, IL (ORD-O'Hare Intl.) to City of Colorado Springs Municipal Airport. Look for a bargain fare and take to the skies with United Airlines or American Airlines.
What is the shortest flight from Chicago to Pueblo?
Traveling from Chicago, IL (ORD-O'Hare Intl.) to City of Colorado Springs Municipal Airport takes at least 3 hours and 15 minutes. Indulge in a tipple and read a few magazines — it's the perfect opportunity to chill out.
What airlines fly from Chicago to Pueblo most frequently?
The carriers that fly frequently between Chicago, IL (ORD-O'Hare Intl.) and Colorado Springs Airport (COS) include United Airlines (UA). This popular option offers 60 flights on the route each month. If you can't find the right flight there, check out American Airlines (AA). This airline is a fantastic alternative and operates 30 flights from Chicago to Pueblo each month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.