$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, Apr 3 - Sun, Apr 5
ORD
O'Hare Intl.
COS
Colorado Springs
$986 Roundtrip, found 1 day ago
$986
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Apr 3 from O'Hare Intl. to Colorado Springs, returning Sun, Apr 5, priced at $986 found 1 day ago
Fri, Apr 3 - Sun, Apr 5
RFD
Greater Rockford
COS
Colorado Springs
$1,058 Roundtrip, found 1 day ago
$1,058
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Apr 3 from Greater Rockford to Colorado Springs, returning Sun, Apr 5, priced at $1,058 found 1 day ago
Fri, Apr 3 - Sun, Apr 5
MDW
Midway Intl.
COS
Colorado Springs
$1,083 Roundtrip, found 1 day ago
$1,083
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Apr 3 from Midway Intl. to Colorado Springs, returning Sun, Apr 5, priced at $1,083 found 1 day ago

Airfares from $116 One Way, $292 Round Trip from Chicago to Pueblo

Prices starting at $292 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.

Tue, Jun 16 - Tue, Jun 23
ORD
Chicago
COS
Colorado Springs
$292 Roundtrip, found 1 day ago
$292
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jun 16 from Chicago to Colorado Springs, returning Tue, Jun 23, priced at $292 found 1 day ago
Tue, Jun 16 - Tue, Jun 23
ORD
Chicago
COS
Colorado Springs
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jun 16 from Chicago to Colorado Springs, returning Tue, Jun 23, priced at $302 found 1 day ago
Tue, Jun 16 - Tue, Jun 23
MDW
Chicago
COS
Colorado Springs
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jun 16 from Chicago to Colorado Springs, returning Tue, Jun 23, priced at $312 found 1 day ago
Tue, Jun 16 - Tue, Jun 23
ORD
Chicago
COS
Colorado Springs
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jun 16 from Chicago to Colorado Springs, returning Tue, Jun 23, priced at $312 found 1 day ago
Tue, Jun 16 - Tue, Jun 23
MDW
Chicago
COS
Colorado Springs
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jun 16 from Chicago to Colorado Springs, returning Tue, Jun 23, priced at $317 found 1 day ago

Pueblo economy flight packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Pueblo
2.5-star property

Baymont by Wyndham Pueblo

8/10 Very Good! (1,173 reviews)

May 13 - May 16

3 night stay

Chicago (CHI) to Pueblo (PUB)

Southwest Airlines • Coach

Pueblo (PUB) to Chicago (CHI)

Frontier Airlines • Coach
Price was $273, price is now $258 per person
$258
per person
found 1 day ago
We had a king Bed which is very comfortable. Room is starting to show its age. Sink tap tended to Drip. Sink took a long time to drain. Carpet had major stains that need to be cleaned. Furniture showing its age by being shipped. TV and internet was good. Breakfast was good. It had hot and cold items. Hot Items included biscuits and gravy, Waffles, And Jimmy Dean's breakfast Sandwich which you heatup in microwave. Staff were friendly and accommodating.

Reviewed on Nov 1, 2025

Quality Inn & Suites Pueblo West
2.5-star property

Quality Inn & Suites Pueblo West

8.4/10 Very Good! (1,001 reviews)

May 13 - May 16

3 night stay

Chicago (CHI) to Pueblo (PUB)

Southwest Airlines • Coach

Pueblo (PUB) to Chicago (CHI)

Frontier Airlines • Coach
Price was $332, price is now $318 per person
$318
per person
found 1 day ago
We booked 3 rooms for a family weekend in Pueblo West. The rooms were clean, the breakfast was simple but good with waffles, eggs, sausage, hash browns, yogurt, breads and good coffee. We enjoyed our stay. The ice machine was out of order so we had to do without ice in our drinks.

Reviewed on Jul 14, 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.