Cheap flights from Chicago (CHI) to Telluride (DRO)

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Lowest round trip fares by airline from Chicago and Telluride

Cheapest prices ($183 One Way, $403 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Telluride

Mountainside Inn

Mountainside Inn

2.5 out of 5
333 S Davis St, Telluride, CO, 81435
Stay at this ski hotel in Telluride. Enjoy free WiFi, free parking, and a terrace. Our guests praise the helpful staff and the overall value in our reviews. ...
3.5/5 Good! (4 reviews)
"Great location, friendly staff, complimentary tea and coffee"

Reviewed on Sep 29, 2020

Mountainside Inn
The Victorian Inn

The Victorian Inn

3.5 out of 5
401 W Pacific Ave, Telluride, CO, 81435
The price is $225 per night from Jun 6 to Jun 7
Stay at this 3.5-star business-friendly hotel in Telluride. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
3.8/5 Good! (4 reviews)
CLOSE TO EVERYTHING OLD BUILDING NOT SO WELL KEPT
"WE STAYED 4 NIGHTS, SECOND DAY THEY FORGOT TO CLEAN OUR ROOM, THIRD DAY 12 PM AND STILL NOT CLEANED I WENT TO THE OFFICE TO MAKE SURE THEY WOULD CLEAN, SHE WAS UPSET, EVEN THOUGH I MADE A POINT OF LETTING HER KNOW THE PREVIOUS DAY IT WAS NOT DONE. CONTINENTAL BREAKFAST VERY POOR. WENT TO GET COFFEE ..."

Reviewed on Aug 7, 2018

The Victorian Inn
The Angler Inn

The Angler Inn

3 out of 5
22332 Hwy 145, Placerville, CO, 81430
Stay at this 3-star hotel in Placerville. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the comfy rooms in our reviews. Popular attractions ...
5/5 Exceptional! (1 review)
"The staff were extremely helpful to us, especially after you guys (cheaptickets) failed to communicate the message about having a dog with us. We actually wound up with a BETTER room, thanks to Julie. And Amy was willing to hook us up with some furniture for our daughter/son-in-law, who recently ..."

Reviewed on May 31, 2017

The Angler Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Telluride

Origin Chicago
Destination Telluride
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
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Cheap flights from Chicago to Telluride

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Save Even More Time and Money With a Telluride Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Telluride vacation that you can't get when you book flights and hotel separately.

Relax in Telluride With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.