$62 Cheap flight deals from Madison (MSN) to Winter Park (DEN)

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This Weekend's Flight Deals from Madison to Winter Park

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Oct 3 - Mon, Oct 6
MSN
Dane County Regional
DEN
Denver Intl.
$211 Roundtrip, found 9 hours ago
$211
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Fri, Oct 3 from Dane County Regional to Denver Intl., returning Mon, Oct 6, priced at $211 found 9 hours ago

Airfares from $62 One Way, $119 Round Trip from Madison to Winter Park

Prices starting at $119 for return flights and $62 for one-way flights to Winter Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Oct 27 - Fri, Oct 31
MSN
Madison
DEN
Denver
$119 Roundtrip, found 6 days ago
$119
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Oct 27 from Madison to Denver, returning Fri, Oct 31, priced at $119 found 6 days ago
Fri, Oct 31 - Fri, Nov 14
MSN
Madison
DEN
Denver
$121 Roundtrip, found 6 days ago
$121
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Madison to Denver, returning Fri, Nov 14, priced at $121 found 6 days ago
Mon, Nov 10 - Mon, Nov 17
MSN
Madison
DEN
Denver
$129 Roundtrip, found 6 days ago
$129
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Madison to Denver, returning Mon, Nov 17, priced at $129 found 6 days ago
Thu, Oct 30 - Fri, Oct 31
MSN
Madison
DEN
Denver
$133 Roundtrip, found 6 days ago
$133
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Madison to Denver, returning Fri, Oct 31, priced at $133 found 6 days ago
Mon, Nov 10 - Fri, Nov 14
MSN
Madison
DEN
Denver
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Madison to Denver, returning Fri, Nov 14, priced at $134 found 3 days ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Glenwood Springs Inn
2.0-star property

Glenwood Springs Inn

8.8/10 Excellent! (1,454 reviews)

Nov 20 - Nov 24

4 night stay

Madison (MSN) to Denver (DEN)

United • Non-stop roundtrip • Coach
Price was $745, price is now $543 per person
$543
per person
found 1 day ago
We have stayed in Glenwood Springs near the hot springs pool several times. This is the first time we have stayed at this property. The outside of this property has not changed for years and is certainly in need of a face;lift. That said, the room was comfortable and quiet. The environmental controls were good. There was a good-sized refrigerator with a small freezer. The breakfast was more than adequate. The property is within easy walking distance of the pool. All in all, this was a good place to stay and was a good value.

Reviewed on Sep 19, 2025

Cozy Edwards Retreat w/ Fireplace, Near Ski Resort Osprey Nest by Avantstay
3.0-star property

Cozy Edwards Retreat w/ Fireplace, Near Ski Resort Osprey Nest by Avantstay

No reviews

Nov 20 - Nov 24

4 night stay

Madison (MSN) to Denver (DEN)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,149, price is now $2,371 per person
$2,371
per person
found 1 day ago
Beaver Creek Village
3.5-star property

Beaver Creek Village

9/10 Wonderful! (2 reviews)

Nov 20 - Nov 24

4 night stay

Madison (MSN) to Denver (DEN)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,653, price is now $1,276 per person
$1,276
per person
found 1 day ago
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More About Flying To Winter Park from Madison

Route Information for Flights from Madison to Winter Park

Origin Airport IATA Code
MSN
Destination Airport IATA Code
DEN
Distance
823 mi
Direct Flight Airlines
United Airlines
Earliest Flight Arrival
4:25PM UTC
Latest Flight Arrival
11:57PM UTC

Madison to Winter Park

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.