$45 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.

Sun, Nov 23 - Fri, Nov 28
MSN
Dane County Regional
DEN
Denver Intl.
$91 Roundtrip, found 5 days ago
$91
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Nov 23 from Dane County Regional to Denver Intl., returning Fri, Nov 28, priced at $91 found 5 days ago

Airfares from $45 One Way, $90 Round Trip from Madison to Winter Park

Prices starting at $90 for return flights and $45 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, Nov 24 - Tue, Nov 25
MSN
Madison
DEN
Denver
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 24 from Madison to Denver, returning Tue, Nov 25, priced at $90 found 1 day ago
Sun, Dec 21 - Tue, Dec 30
MSN
Madison
DEN
Denver
$114 Roundtrip, found 1 hour ago
$114
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Dec 21 from Madison to Denver, returning Tue, Dec 30, priced at $114 found 1 hour ago
Tue, Nov 25 - Wed, Nov 26
MSN
Madison
DEN
Denver
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Nov 25 from Madison to Denver, returning Wed, Nov 26, priced at $117 found 5 days ago
Sun, Dec 21 - Mon, Jan 5
MSN
Madison
DEN
Denver
$119 Roundtrip, found 5 days ago
$119
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Dec 21 from Madison to Denver, returning Mon, Jan 5, priced at $119 found 5 days ago
Sun, Dec 21 - Mon, Dec 29
MSN
Madison
DEN
Denver
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Dec 21 from Madison to Denver, returning Mon, Dec 29, priced at $120 found 5 days ago

Winter Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Denver Downtown by IHG
3.0-star property

Holiday Inn Express Denver Downtown by IHG

14/10 Exceptional! (1,558 reviews)

Dec 27 - Jan 3

7 night stay

Madison (MSN) to Denver (DEN)

United • Roundtrip • Coach
Price was $1,476, price is now $1,161 per person
$1,161
per person
found 2 hours ago
the refrigerator was not connected. there were no cups, coffee maker, and air conditioning was central so the rooms were pretty cold. but those are minor things overall service was good and the rooms were nice and clean.

Reviewed on Nov 8, 2025

The Brown Palace Hotel and Spa, Autograph Collection
4.5-star property

The Brown Palace Hotel and Spa, Autograph Collection

17.2/10 Exceptional! (1,007 reviews)

Dec 27 - Jan 3

7 night stay

Madison (MSN) to Denver (DEN)

United • Roundtrip • Coach
Price was $1,581, price is now $1,235 per person
$1,235
per person
found 2 hours ago
Clean room. Great staff. Seemed confused tho at time. Dinner at the Palace Arms was ok. Oyster Rock were horrible. Cold. Gross. Dessert menu at Ships Tavern was awful. Food was great tho. Room water a complete failure.

Reviewed on Nov 11, 2025

Hilton Denver City Center
4.0-star property

Hilton Denver City Center

17.2/10 Exceptional! (1,092 reviews)

Dec 27 - Jan 3

7 night stay

Madison (MSN) to Denver (DEN)

United • Roundtrip • Coach
Price was $1,659, price is now $1,313 per person
$1,313
per person
found 2 hours ago
I enjoyed the staff. Everyone was very friendly and helpful. The hotel food was ok, but the near dining options were great.

Reviewed on Sep 3, 2025

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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

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.