$81 Cheap flight deals from Chicago (CHI) to Pueblo (COS)

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Airfares from $81 One Way, $177 Round Trip from Chicago to Pueblo

Prices starting at $177 for return flights and $81 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.

Wed, Feb 11 - Wed, Feb 18
ORD
Chicago
COS
Colorado Springs
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select United flight, departing Wed, Feb 11 from Chicago to Colorado Springs, returning Wed, Feb 18, priced at $177 found 1 day ago
Wed, Feb 11 - Wed, Feb 18
ORD
Chicago
COS
Colorado Springs
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select United flight, departing Wed, Feb 11 from Chicago to Colorado Springs, returning Wed, Feb 18, priced at $179 found 1 day ago
Wed, Feb 25 - Sat, Feb 28
ORD
Chicago
COS
Colorado Springs
$190 Roundtrip, found 9 hours ago
$190
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Feb 25 from Chicago to Colorado Springs, returning Sat, Feb 28, priced at $190 found 9 hours ago
Wed, Feb 11 - Wed, Feb 18
ORD
Chicago
COS
Colorado Springs
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select United flight, departing Wed, Feb 11 from Chicago to Colorado Springs, returning Wed, Feb 18, priced at $196 found 1 day ago
Wed, Feb 25 - Sat, Feb 28
MDW
Chicago
COS
Colorado Springs
$201 Roundtrip, found 9 hours ago
$201
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Feb 25 from Chicago to Colorado Springs, returning Sat, Feb 28, priced at $201 found 9 hours ago

Pueblo economy flight packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn Pueblo North
2.5-star property

Quality Inn Pueblo North

8.6/10 Excellent! (1,000 reviews)

Feb 26 - Mar 2

4 night stay

Chicago (ORD) to Pueblo (PUB)

Southwest Airlines • Coach

Pueblo (PUB) to Chicago (ORD)

Frontier Airlines • Coach
Price was $398, price is now $352 per person
$352
per person
found 15 hours ago
Room was clean. Bed was good. Noise from nearby roads was noticeable, but not too bad. The door keys didn’t work well.

Reviewed on Nov 7, 2025

Motel 6 Canon City, CO
2.0-star property

Motel 6 Canon City, CO

7/10 Good! (427 reviews)

Mar 14 - Mar 17

3 night stay

Chicago (MDW) to Pueblo (PUB)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $405, price is now $393 per person
$393
per person
found 1 day ago
Floor in room not very clean. Property was as expected for a cheaper motel. they definitely need need beds. Sagging and soft

Reviewed on Aug 11, 2023

Extended Stay America Premier Suites - Pueblo
2.5-star property

Extended Stay America Premier Suites - Pueblo

8.8/10 Excellent! (379 reviews)

Mar 15 - Mar 17

2 night stay

Chicago (ORD) to Pueblo (PUB)

American Airlines • Roundtrip • Coach
Price was $418, price is now $414 per person
$414
per person
found 1 day ago
good service -good area

Reviewed on Mar 13, 2025

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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

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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.