$74 Cheap flight deals from Chicago (CHI) to Winter Park (DEN)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
This Weekend's Flight Deals from Chicago 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.
Airfares from $74 One Way, $141 Round Trip from Chicago to Winter Park
Prices starting at $141 for return flights and $74 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.
Winter Park economy flight packages
The Slate Denver, Tapestry Collection By Hilton
Aug 7 - Aug 10
Chicago (CHI) to Denver (DEN)
Reviewed on Apr 8, 2025
The Rally Hotel at McGregor Square
Aug 7 - Aug 10
Chicago (CHI) to Denver (DEN)
Reviewed on Apr 22, 2025
Winter Park first class flight packages
DoubleTree by Hilton Denver International Airport
Aug 9 - Aug 14
Chicago (ORD) to Denver (DEN)
Denver (DEN) to Chicago (ORD)
Reviewed on Apr 14, 2025
The Crawford Hotel
Aug 9 - Aug 14
Chicago (ORD) to Denver (DEN)
Denver (DEN) to Chicago (ORD)
Reviewed on May 26, 2025
The Slate Denver, Tapestry Collection By Hilton
Aug 9 - Aug 14
Chicago (ORD) to Denver (DEN)
Denver (DEN) to Chicago (ORD)
Reviewed on Apr 8, 2025
More About Flying To Winter Park from Chicago
Route Information for Flights from Chicago to Winter Park
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | DEN |
Distance | 886 mi |
Direct Flight Airlines | American Airlines, Qatar Airways, JAL, Air Canada, Austrian, Aer Lingus, Emirates, Copa Airlines, Swiss, United Airlines, Frontier Airlines, Cathay Pacific, Turkish Airlines, Southwest Airlines, Royal Jordanian, Iberia, Brussels Airlines, Lufthansa, Gulf Air, British Airways |
Earliest Flight Arrival | 12:43PM UTC |
Latest Flight Arrival | 5:22AM UTC |
Chicago to Winter Park
Rack up your savings with low-cost flights from Chicago to Winter Park with Orbitz On-the-Go. Orbitz On-the-Go offers mobile-only deals and cutting edge mobile tools to help you find bargain flights from Chicago to Winter Park.
Mobile-Only Deals on Chicago to Winter Park flights
Find guaranteed low prices on Chicago to Winter Park flights using Orbitz On-the-Go. You can book discount domestic flights from Chicago to Winter Park, and international tickets on Chicago to Winter Park flights using our mobile site and apps.
Free Alerts Are No Surprise
Not only will you find cheap tickets on flights from Chicago to Winter Park, but Orbitz free alerts will keep you up to speed on flight status, plus gate and baggage claim details. Receive instant updates via your choice of email, voice or text. Orbitz keeps you easily on task and on budget.
Share Itineraries on Flights from Chicago to Winter Park
Are you traveling for business, pleasure or a combination of both? Keep family, friends and business contacts posted on flight and gate info. Just use MyTrips for iPhone, Android and web phones like Blackberry and Windows.
Add Smiles to Your Miles with Sales and Deals on Chicago to Winter Park Flights
Travel planning is easy when you store your frequent flyer and loyalty program information on your Orbitz account. Then snag a low-fare air ticket on Chicago to Winter Park flights, and you’re done. No muss, no fuss. Your miles will fly by with Orbitz On-the-Go cutting edge mobile tools and guaranteed low prices.
Flights from Chicago
- Chicago to New York
- Chicago to Orlando
- Chicago to Houston
- Chicago to Phoenix
- Chicago to Los Angeles
- Chicago to London
- Chicago to Dallas
- Chicago to Washington
- Chicago to Toronto
- Chicago to Paris
- Chicago to New Orleans
- Chicago to Rome
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Kansas City
- Chicago to Sacramento
- Chicago to Hartford
- Chicago to Atlantic City
Top Trending
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.