$299 Cheap Flights from Telluride (TEX) to Chicago (ORD)

View $299 flight on Wed, Feb 25, 2026Opens in a new window

Popular airlines from Telluride, CO (TEX-Telluride Regional) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Telluride to Chicago (TEX-ORD)

Prices were available within the past 7 days and start at $299 for one-way flights and $691 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, Oct 22 - Tue, Oct 28
TEX
Telluride
ORD
Chicago
$691 Roundtrip, found 4 days ago
$691
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Oct 22 from Telluride to Chicago, returning Tue, Oct 28, priced at $691 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Feb 23 - Sat, Feb 28
TEX
Telluride
ORD
Chicago
$735 Roundtrip, found 1 day ago
$735
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Feb 23 from Telluride to Chicago, returning Sat, Feb 28, priced at $735 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sat, Oct 18 - Sat, Oct 25
TEX
Telluride
ORD
Chicago
$736 Roundtrip, found 6 days ago
$736
Roundtrip
found 6 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sat, Oct 18 from Telluride to Chicago, returning Sat, Oct 25, priced at $736 found 6 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Feb 23 - Sat, Feb 28
TEX
Telluride
ORD
Chicago
$740 Roundtrip, found 1 day ago
$740
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Feb 23 from Telluride to Chicago, returning Sat, Feb 28, priced at $740 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Feb 23 - Sat, Feb 28
TEX
Telluride
ORD
Chicago
$750 Roundtrip, found 1 day ago
$750
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Feb 23 from Telluride to Chicago, returning Sat, Feb 28, priced at $750 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Oct 22 - Mon, Oct 27
TEX
Telluride
ORD
Chicago
$753 Roundtrip, found 4 days ago
$753
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Oct 22 from Telluride to Chicago, returning Mon, Oct 27, priced at $753 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Oct 21 - Sun, Oct 26
TEX
Telluride
ORD
Chicago
$784 Roundtrip, found 4 days ago
$784
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Oct 21 from Telluride to Chicago, returning Sun, Oct 26, priced at $784 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Wed, Oct 22 - Thu, Oct 23
TEX
Telluride
ORD
Chicago
$784 Roundtrip, found 4 days ago
$784
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Oct 22 from Telluride to Chicago, returning Thu, Oct 23, priced at $784 found 4 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Feb 23 - Sat, Feb 28
TEX
Telluride
ORD
Chicago
$792 Roundtrip, found 1 day ago
$792
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Feb 23 from Telluride to Chicago, returning Sat, Feb 28, priced at $792 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Oct 20 - Tue, Oct 28
TEX
Telluride
ORD
Chicago
$806 Roundtrip, found 4 days ago
$806
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Oct 20 from Telluride to Chicago, returning Tue, Oct 28, priced at $806 found 4 days ago

Frequently asked questions

How much does a flight from Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $299 or cheap return flight from $691 from Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD) 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 Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD)?
Flying in October may help you find better deals, as it's the cheapest month for flights between TEX and ORD. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest TEX to ORD flight.
How many flights per day from Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD)?
There are no daily nonstop flights departing from Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD). But you can book flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time.
What day of the week has the most flights from TEX to ORD?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can change based on a range of factors, including the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD)?
To touch down at O'Hare Intl. Airport (ORD) on schedule, choose a flight that takes off from Telluride Regional Airport (TEX) before 3 PM. The chance 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 Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from TEX to ORD are usually more expensive. To lock in the best rates, start looking for flights early. That being said, if you're flexible with your travel dates, it's possible to find a cheap ticket right before your journey.
Is it cheaper to book a TEX to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a TEX to ORD flight and hotel package with Expedia could lead to significant savings. What's more, having everything in one place will take the stress out of planning your trip. Simply pick your flights and choose from our extensive range of hotels, then tailor your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Telluride Regional Airport (TEX) to O'Hare Intl. Airport (ORD)?
If you reserved your TEX to ORD flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Travel information

Origin airport
Telluride Regional
Destination airport
O'Hare Intl.
Roundtrip price
$691
Distance
1091 mi

Book with confidence

Telluride to Chicago Flights

The cheapest times to fly from Telluride 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 Telluride to Chicago are during the month of October. You can find some of the cheapest flights from Telluride to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Telluride to Chicago

Sunday is one of the best days to book for cheap flights from Telluride 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 Telluride 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 Telluride to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $299 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 Telluride 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 Telluride 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.

 

Telluride to Chicago Flights

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*Available to One Key members.