$297 Cheap Flights from Chicago (MDW) to Pueblo (PUB)

View $297 flight on Tue, Oct 7, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Pueblo, CO (PUB-Pueblo Memorial)

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Cheap Flights from Chicago to Pueblo (MDW-PUB)

Prices were available within the past 7 days and start at $297 for one-way flights and $389 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Dec 3 - Wed, Dec 10
MDW
Chicago
PUB
Pueblo
$389 Roundtrip, found 3 days ago
$389
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Dec 3 from Chicago to Pueblo, returning Wed, Dec 10, priced at $389 found 3 days ago
Delta
Sun, Jan 11 - Tue, Jan 13
MDW
Chicago
PUB
Pueblo
$439 Roundtrip, found 5 days ago
$439
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Jan 11 from Chicago to Pueblo, returning Tue, Jan 13, priced at $439 found 5 days ago
Delta
Fri, Dec 5 - Mon, Dec 8
MDW
Chicago
PUB
Pueblo
$460 Roundtrip, found 3 days ago
$460
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 5 from Chicago to Pueblo, returning Mon, Dec 8, priced at $460 found 3 days ago
Delta
Fri, Dec 5 - Mon, Dec 8
MDW
Chicago
PUB
Pueblo
$495 Roundtrip, found 3 days ago
$495
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 5 from Chicago to Pueblo, returning Mon, Dec 8, priced at $495 found 3 days ago
Delta
Fri, Dec 5 - Mon, Dec 8
MDW
Chicago
PUB
Pueblo
$501 Roundtrip, found 3 days ago
$501
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 5 from Chicago to Pueblo, returning Mon, Dec 8, priced at $501 found 3 days ago
Delta
Fri, Dec 5 - Mon, Dec 8
MDW
Chicago
PUB
Pueblo
$536 Roundtrip, found 3 days ago
$536
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 5 from Chicago to Pueblo, returning Mon, Dec 8, priced at $536 found 3 days ago
Delta
Fri, Dec 5 - Mon, Dec 8
MDW
Chicago
PUB
Pueblo
$566 Roundtrip, found 3 days ago
$566
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 5 from Chicago to Pueblo, returning Mon, Dec 8, priced at $566 found 3 days ago
Delta
Fri, Dec 5 - Mon, Dec 8
MDW
Chicago
PUB
Pueblo
$601 Roundtrip, found 3 days ago
$601
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 5 from Chicago to Pueblo, returning Mon, Dec 8, priced at $601 found 3 days ago
Delta
Fri, Nov 28 - Mon, Dec 1
MDW
Chicago
PUB
Pueblo
$801 Roundtrip, found 3 days ago
$801
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Nov 28 from Chicago to Pueblo, returning Mon, Dec 1, priced at $801 found 3 days ago
Delta
Fri, Nov 28 - Mon, Dec 1
MDW
Chicago
PUB
Pueblo
$891 Roundtrip, found 3 days ago
$891
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Nov 28 from Chicago to Pueblo, returning Mon, Dec 1, priced at $891 found 3 days ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB) cost?
Grab a cheap one-way flight from $297 or cheap return flight from $389 from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB)?
Planning your trip for December can help you save, as it's the cheapest month for flights between MDW and PUB. You'll typically find the lowest fares during the off-season.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB)?
To find the cheapest airline flying from MDW to PUB, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB)?
Direct flights from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to PUB?
Generally you'll have the most choice when it comes to flights on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB)?
Choose a flight from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB) that takes off before 3 PM to reduce the risk of delays and cancellations. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Pueblo from Midway Intl. Airport (MDW)?
Browse your flight options from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS). This is the only Pueblo airport you can touch down at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB) last-minute?
Last-minute fares from MDW to PUB are generally more expensive. To secure the lowest rates, start searching for flights well ahead of time. That being said, if your travel plans are flexible, you may land a cheap ticket right before your trip.
Is it cheaper to book a MDW to PUB flight and hotel package?
Securing a MDW to PUB flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our impressive range of hotels and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Pueblo Memorial Airport (PUB)?
If you booked your MDW to PUB flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Pueblo Memorial
Roundtrip price
$389
Distance
917 mi

Book with confidence

Book with confidence

Chicago to Pueblo Flights

The cheapest times to fly from Chicago to Pueblo

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Pueblo are during the month of December. You can find some of the cheapest flights from Chicago to Pueblo with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Pueblo

Sunday is one of the best days to book for cheap flights from Chicago to Pueblo: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Pueblo

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Pueblo in 2025. You can also book with separate airlines for your outbound and return journeys, from $297 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Pueblo flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Pueblo airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Pueblo Flights

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Explore a world of travel with Expedia

*Available to One Key members.