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

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Pueblo to Chicago (PUB-MDW)

Prices were available within the past 7 days and start at for one-way flights and $616 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Aug 15 - Mon, Aug 18
PUB
Pueblo
MDW
Chicago
$616 Roundtrip, found 19 hours ago
$616
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Aug 15 from Pueblo to Chicago, returning Mon, Aug 18, priced at $616 found 19 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Aug 15 - Mon, Aug 18
PUB
Pueblo
MDW
Chicago
$686 Roundtrip, found 19 hours ago
$686
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Aug 15 from Pueblo to Chicago, returning Mon, Aug 18, priced at $686 found 19 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Jul 18 - Fri, Jul 25
PUB
Pueblo
MDW
Chicago
$726 Roundtrip, found 19 hours ago
$726
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Jul 18 from Pueblo to Chicago, returning Fri, Jul 25, priced at $726 found 19 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Aug 15 - Mon, Aug 18
PUB
Pueblo
MDW
Chicago
$766 Roundtrip, found 19 hours ago
$766
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Aug 15 from Pueblo to Chicago, returning Mon, Aug 18, priced at $766 found 19 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Jul 18 - Fri, Jul 25
PUB
Pueblo
MDW
Chicago
$806 Roundtrip, found 19 hours ago
$806
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Jul 18 from Pueblo to Chicago, returning Fri, Jul 25, priced at $806 found 19 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Jul 18 - Fri, Jul 25
PUB
Pueblo
MDW
Chicago
$906 Roundtrip, found 19 hours ago
$906
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Jul 18 from Pueblo to Chicago, returning Fri, Jul 25, priced at $906 found 19 hours ago
Flights from Pueblo (PUB) to Chicago (MDW)
Origin airport
Pueblo Memorial
Destination airport
Midway Intl.
Roundtrip price
$616
Distance
917 mi

Pueblo to Chicago Flights

The cheapest times to fly from Pueblo to Chicago

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 Pueblo to Chicago are during the month of August. You can find some of the cheapest flights from Pueblo to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Pueblo to Chicago

Sunday is one of the best days to book for cheap flights from Pueblo to Chicago: 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 Pueblo to Chicago

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 Pueblo to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from 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 Pueblo to Chicago 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 Pueblo to Chicago 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.

 

Frequently asked questions

How much does a flight from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from PUB to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from PUB to MDW?
The cheapest flights from PUB to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW)?
Although Pueblo, CO (PUB-Pueblo Memorial) has no direct flights to Midway Intl. Airport (MDW), other airports have nonstop options. Taking off from Colorado Springs Airport (COS) will get you to Chicago without any detours.
What is the cheapest airline that flies from PUB to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from PUB to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW)?
There aren't any daily direct flights departing from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from PUB to MDW?
Usually you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary depending on the airline, time of year 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 Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Later departures have a 22% higher chance of being canceled.**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.
Is it cheaper to buy a plane ticket from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from PUB to MDW are typically more expensive. For the best rates, start looking for flights well in advance. That being said, if you can play around with your travel dates, it's possible to score a cheap ticket right before your trip.
Is it cheaper to book a PUB to MDW flight and hotel package?
Securing a PUB to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Choose from our extensive range of hotels and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW)?
In most instances, you can cancel or modify your PUB to MDW flight. However, additional fees may apply, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you need more information, visit our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.