$375 Cheap Flights from Pueblo (PUB) to Chicago (ORD)

View $375 flight on Fri, Oct 24, 2025Opens in a new window

Popular airlines from Pueblo, CO (PUB-Pueblo Memorial) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Pueblo to Chicago (PUB-ORD)

Prices were available within the past 7 days and start at $375 for one-way flights and $358 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Dec 11 - Tue, Dec 16
PUB
Pueblo
ORD
Chicago
$358 Roundtrip, found 4 days ago
$358
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Dec 11 from Pueblo to Chicago, returning Tue, Dec 16, priced at $358 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Dec 12 - Sat, Dec 13
PUB
Pueblo
ORD
Chicago
$364 Roundtrip, found 4 days ago
$364
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Dec 12 from Pueblo to Chicago, returning Sat, Dec 13, priced at $364 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Dec 14 - Mon, Dec 15
PUB
Pueblo
ORD
Chicago
$366 Roundtrip, found 4 days ago
$366
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Dec 14 from Pueblo to Chicago, returning Mon, Dec 15, priced at $366 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Dec 13 - Tue, Dec 16
PUB
Pueblo
ORD
Chicago
$368 Roundtrip, found 4 days ago
$368
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Dec 13 from Pueblo to Chicago, returning Tue, Dec 16, priced at $368 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Oct 31 - Thu, Nov 6
PUB
Pueblo
ORD
Chicago
$372 Roundtrip, found 3 days ago
$372
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Oct 31 from Pueblo to Chicago, returning Thu, Nov 6, priced at $372 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Dec 4 - Tue, Dec 9
PUB
Pueblo
ORD
Chicago
$378 Roundtrip, found 3 hours ago
$378
Roundtrip
found 3 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Dec 4 from Pueblo to Chicago, returning Tue, Dec 9, priced at $378 found 3 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Dec 24 - Mon, Jan 5
PUB
Pueblo
ORD
Chicago
$379 Roundtrip, found 3 hours ago
$379
Roundtrip
found 3 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Dec 24 from Pueblo to Chicago, returning Mon, Jan 5, priced at $379 found 3 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Dec 14 - Tue, Dec 16
PUB
Pueblo
ORD
Chicago
$380 Roundtrip, found 4 days ago
$380
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Dec 14 from Pueblo to Chicago, returning Tue, Dec 16, priced at $380 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Nov 30 - Tue, Dec 9
PUB
Pueblo
ORD
Chicago
$390 Roundtrip, found 3 hours ago
$390
Roundtrip
found 3 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Nov 30 from Pueblo to Chicago, returning Tue, Dec 9, priced at $390 found 3 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Dec 13 - Mon, Dec 15
PUB
Pueblo
ORD
Chicago
$391 Roundtrip, found 4 days ago
$391
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Dec 13 from Pueblo to Chicago, returning Mon, Dec 15, priced at $391 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Dec 3 - Wed, Dec 10
PUB
Pueblo
ORD
Chicago
$393 Roundtrip, found 3 hours ago
$393
Roundtrip
found 3 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Dec 3 from Pueblo to Chicago, returning Wed, Dec 10, priced at $393 found 3 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Dec 4 - Wed, Dec 10
PUB
Pueblo
ORD
Chicago
$399 Roundtrip, found 3 hours ago
$399
Roundtrip
found 3 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Dec 4 from Pueblo to Chicago, returning Wed, Dec 10, priced at $399 found 3 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Fri, Dec 26 - Mon, Jan 5
PUB
Pueblo
ORD
Chicago
$402 Roundtrip, found 3 hours ago
$402
Roundtrip
found 3 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Dec 26 from Pueblo to Chicago, returning Mon, Jan 5, priced at $402 found 3 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Dec 11 - Mon, Dec 15
PUB
Pueblo
ORD
Chicago
$403 Roundtrip, found 4 days ago
$403
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Dec 11 from Pueblo to Chicago, returning Mon, Dec 15, priced at $403 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Dec 14 - Mon, Dec 15
PUB
Pueblo
ORD
Chicago
$404 Roundtrip, found 4 days ago
$404
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Dec 14 from Pueblo to Chicago, returning Mon, Dec 15, priced at $404 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Dec 13 - Sun, Dec 14
PUB
Pueblo
ORD
Chicago
$405 Roundtrip, found 4 days ago
$405
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Dec 13 from Pueblo to Chicago, returning Sun, Dec 14, priced at $405 found 4 days ago

Frequently asked questions

How much does a flight from Pueblo Memorial Airport (PUB) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $375 or cheap return flight from $358 from Pueblo Memorial Airport (PUB) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Pueblo Memorial Airport (PUB) to O'Hare Intl. Airport (ORD)?
December is the most affordable month to fly from PUB to ORD. Avoiding peak travel times is often the key to finding better deals on flights.
Which airlines fly direct from Pueblo Memorial Airport (PUB) to O'Hare Intl. Airport (ORD)?
You can't fly directly from Pueblo, CO (PUB-Pueblo Memorial) to O'Hare Intl. Airport (ORD). However, you can find other airports with nonstop flights. Hop on your plane at Colorado Springs Airport (COS) and fly straight to Chicago without a layover.
What is the cheapest airline that flies from Pueblo Memorial Airport (PUB) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest PUB to ORD flight.
How many flights per day from Pueblo Memorial Airport (PUB) to O'Hare Intl. Airport (ORD)?
Direct flights from Pueblo Memorial Airport (PUB) to O'Hare Intl. Airport (ORD) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from PUB to ORD?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can change based on a number of factors, including the season and airline.*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 O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) without delays, choose a flight that leaves from Pueblo Memorial Airport (PUB) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 O'Hare Intl. Airport (ORD) last-minute?
Booking your plane ticket from PUB to ORD shortly before your journey is usually more expensive. But if there's some wiggle room with your departure dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a PUB to ORD flight and hotel package?
You'll typically save money by securing a PUB to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. Once you've chosen your preferred accommodations and flights, consider adding extras including activities, car rentals and tours.
Can I cancel or change the date of my flight from Pueblo Memorial Airport (PUB) to O'Hare Intl. Airport (ORD)?
It's generally possible to cancel or reschedule your PUB to ORD flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
Pueblo Memorial
Destination airport
O'Hare Intl.
Roundtrip price
$358
Distance
911 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 December. 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 $375 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.