$116 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, Jan 9 - Sun, Jan 11
MDW
Midway Intl.
COS
Colorado Springs
$344 Roundtrip, found 6 days ago
$344
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jan 9 from Midway Intl. to Colorado Springs, returning Sun, Jan 11, priced at $344 found 6 days ago
Fri, Jan 9 - Sun, Jan 11
ORD
O'Hare Intl.
COS
Colorado Springs
$389 Roundtrip, found 6 days ago
$389
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Jan 9 from O'Hare Intl. to Colorado Springs, returning Sun, Jan 11, priced at $389 found 6 days ago

Airfares from $116 One Way, $232 Round Trip from Chicago to Pueblo

Prices starting at $232 for return flights and $116 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.

Fri, Jan 23 - Mon, Jan 26
ORD
Chicago
COS
Colorado Springs
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 23 from Chicago to Colorado Springs, returning Mon, Jan 26, priced at $232 found 1 day ago
Fri, Jan 23 - Mon, Jan 26
ORD
Chicago
COS
Colorado Springs
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select United flight, departing Fri, Jan 23 from Chicago to Colorado Springs, returning Mon, Jan 26, priced at $242 found 1 day ago
Sun, Jun 28 - Fri, Jul 3
ORD
Chicago
COS
Colorado Springs
$249 Roundtrip, found 10 hours ago
$249
Roundtrip
found 10 hours ago
Select Delta flight, departing Sun, Jun 28 from Chicago to Colorado Springs, returning Fri, Jul 3, priced at $249 found 10 hours ago
Sat, Jun 27 - Thu, Jul 2
ORD
Chicago
COS
Colorado Springs
$251 Roundtrip, found 10 hours ago
$251
Roundtrip
found 10 hours ago
Select United flight, departing Sat, Jun 27 from Chicago to Colorado Springs, returning Thu, Jul 2, priced at $251 found 10 hours ago
Tue, Jun 30 - Sun, Jul 5
ORD
Chicago
COS
Colorado Springs
$254 Roundtrip, found 10 hours ago
$254
Roundtrip
found 10 hours ago
Select United flight, departing Tue, Jun 30 from Chicago to Colorado Springs, returning Sun, Jul 5, priced at $254 found 10 hours ago

Pueblo economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Pueblo-Southgate
2.5-star property

Hampton Inn & Suites Pueblo-Southgate

8.2/10 Very Good! (922 reviews)

Feb 13 - Feb 17

4 night stay

Chicago (CHI) to Pueblo (PUB)

American Airlines • Non-stop • Coach

Pueblo (PUB) to Chicago (CHI)

Denver Air Connection • Non-stop • Coach
Price was $678, price is now $585 per person
$585
per person
found 15 hours ago
Staff was very good to everyone

Reviewed on Sep 24, 2024

Royal Gorge Cabins
3.5-star property

Royal Gorge Cabins

9.6/10 Exceptional! (244 reviews)

Feb 11 - Feb 14

3 night stay

Chicago (ORD) to Pueblo (PUB)

American Airlines • Non-stop • Coach

Pueblo (PUB) to Chicago (ORD)

Denver Air Connection • Non-stop • Coach
Price was $1,025, price is now $885 per person
$885
per person
found 12 hours ago
The cabin is so cute and cozy! We loved it!

Reviewed on Dec 22, 2025

Desert Reef Hot Springs
2.0-star property

Desert Reef Hot Springs

9.4/10 Exceptional! (9 reviews)

Feb 11 - Feb 14

3 night stay

Chicago (ORD) to Pueblo (PUB)

American Airlines • Non-stop • Coach

Pueblo (PUB) to Chicago (ORD)

Denver Air Connection • Non-stop • Coach
Price was $850, price is now $750 per person
$750
per person
found 12 hours ago
Last minute find on our Ladies Lunching Across America Tour. One of our favorite stops! Staff was friendly and helpful, our accommodations were lovely and the grounds a tranquil oasis!

Reviewed on Sep 3, 2024

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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

Great Deals on Flights From Chicago to Pueblo

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Flights That Fit Your Budget

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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.

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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.