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

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

Cheap Flights from Pueblo to Chicago (PUB-MDW)

Prices were available within the past 7 days and start at for one-way flights and $378 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Jan 7 - Sat, Jan 17
PUB
Pueblo
MDW
Chicago
$378 Roundtrip, found 6 days ago
$378
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Jan 7 from Pueblo to Chicago, returning Sat, Jan 17, priced at $378 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Jan 6 - Tue, Feb 3
PUB
Pueblo
MDW
Chicago
$385 Roundtrip, found 3 days ago
$385
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Jan 6 from Pueblo to Chicago, returning Tue, Feb 3, priced at $385 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Jan 13 - Sat, Jan 24
PUB
Pueblo
MDW
Chicago
$387 Roundtrip, found 6 days ago
$387
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Jan 13 from Pueblo to Chicago, returning Sat, Jan 24, priced at $387 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Jan 20 - Fri, Feb 6
PUB
Pueblo
MDW
Chicago
$393 Roundtrip, found 6 days ago
$393
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Jan 20 from Pueblo to Chicago, returning Fri, Feb 6, priced at $393 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Jan 13 - Fri, Jan 30
PUB
Pueblo
MDW
Chicago
$402 Roundtrip, found 6 days ago
$402
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Jan 13 from Pueblo to Chicago, returning Fri, Jan 30, priced at $402 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Dec 24 - Tue, Jan 6
PUB
Pueblo
MDW
Chicago
$413 Roundtrip, found 6 days ago
$413
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Dec 24 from Pueblo to Chicago, returning Tue, Jan 6, priced at $413 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Jan 10 - Fri, Jan 30
PUB
Pueblo
MDW
Chicago
$417 Roundtrip, found 6 days ago
$417
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Jan 10 from Pueblo to Chicago, returning Fri, Jan 30, priced at $417 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Jan 20 - Thu, Feb 5
PUB
Pueblo
MDW
Chicago
$420 Roundtrip, found 6 days ago
$420
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Jan 20 from Pueblo to Chicago, returning Thu, Feb 5, priced at $420 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Jan 7 - Thu, Jan 22
PUB
Pueblo
MDW
Chicago
$429 Roundtrip, found 6 days ago
$429
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Jan 7 from Pueblo to Chicago, returning Thu, Jan 22, priced at $429 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Jan 3 - Sat, Jan 17
PUB
Pueblo
MDW
Chicago
$433 Roundtrip, found 6 days ago
$433
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Jan 3 from Pueblo to Chicago, returning Sat, Jan 17, priced at $433 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Jan 3 - Mon, Jan 19
PUB
Pueblo
MDW
Chicago
$442 Roundtrip, found 6 days ago
$442
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Jan 3 from Pueblo to Chicago, returning Mon, Jan 19, priced at $442 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Jan 18 - Fri, Feb 6
PUB
Pueblo
MDW
Chicago
$444 Roundtrip, found 6 days ago
$444
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Jan 18 from Pueblo to Chicago, returning Fri, Feb 6, priced at $444 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Jan 3 - Fri, Jan 23
PUB
Pueblo
MDW
Chicago
$457 Roundtrip, found 6 days ago
$457
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Jan 3 from Pueblo to Chicago, returning Fri, Jan 23, priced at $457 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Dec 24 - Fri, Jan 9
PUB
Pueblo
MDW
Chicago
$468 Roundtrip, found 6 days ago
$468
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Dec 24 from Pueblo to Chicago, returning Fri, Jan 9, priced at $468 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Jan 18 - Thu, Feb 5
PUB
Pueblo
MDW
Chicago
$471 Roundtrip, found 6 days ago
$471
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Jan 18 from Pueblo to Chicago, returning Thu, Feb 5, priced at $471 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Jan 3 - Thu, Jan 22
PUB
Pueblo
MDW
Chicago
$484 Roundtrip, found 6 days ago
$484
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Jan 3 from Pueblo to Chicago, returning Thu, Jan 22, priced at $484 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Jan 7 - Thu, Jan 8
PUB
Pueblo
MDW
Chicago
$497 Roundtrip, found 3 days ago
$497
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Jan 7 from Pueblo to Chicago, returning Thu, Jan 8, priced at $497 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Dec 27 - Sat, Jan 10
PUB
Pueblo
MDW
Chicago
$498 Roundtrip, found 6 days ago
$498
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Dec 27 from Pueblo to Chicago, returning Sat, Jan 10, priced at $498 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Jan 2 - Sat, Jan 17
PUB
Pueblo
MDW
Chicago
$500 Roundtrip, found 6 days ago
$500
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Jan 2 from Pueblo to Chicago, returning Sat, Jan 17, priced at $500 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Jan 27 - Thu, Feb 12
PUB
Pueblo
MDW
Chicago
$509 Roundtrip, found 6 days ago
$509
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Jan 27 from Pueblo to Chicago, returning Thu, Feb 12, priced at $509 found 6 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $500
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $500

Frequently asked questions

How much does a flight from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight or cheap return flight from $378 from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW)?
The cheapest month to fly from PUB to MDW is January, when demand is low. Off-peak months are usually when you'll find lower airfares between these airports.
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 Pueblo Memorial Airport (PUB) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest PUB to MDW flight.
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.

Travel information

Origin airport
Pueblo Memorial
Destination airport
Midway Intl.
Roundtrip price
$378
Distance
917 mi

Book with confidence

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 January. 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 2026. 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.

 

Pueblo to Chicago Flights

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*Available to One Key members.