Find Private Flights from chicago (ord) to winnipeg (ywg)

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Chicago to Winnipeg Charter Flights & Private Jets

Large Air Taxi

Speedy, powerful twin-engine aircraft for families and groups.

Piper Navajo, Cessna 402 or similar


3h 34m

7

4


$ 15,824USD
total for up to 7 travelers
Customize & Book

Light Jet

Medium-range flights with turbojet speed. Cruise above the weather with high-altitude comfort.

Hawker 400, Citation CJ, Phenom 300 or similar


2h 0m

7

4


$ 16,630USD
total for up to 7 travelers
Customize & Book

Personal Jet

A nice efficient jet option for a small group with a short to medium-range mission.

Cirrus Visionjet, Embraer Phenom, Citation Mustang, Eclipse 500 or similar


2h 5m

4

2


$ 16,931USD
total for up to 4 travelers
Customize & Book

Executive Air Taxi

Your turbo-powered hauler. Fits moderate groups with luggage, including car seats, strollers, bikes, skis, and golf clubs.

Pilatus PC-12, Beechcraft King Air, Piper Meridian, Cessna Conquest, Socata TBM or similar


2h 48m

5-8

6


$ 17,932USD
total for up to 5-8 travelers
Customize & Book

Midsize Jet

Many midsize and most "super midsize" jets have transcontinental range for your group of as many as 8 passengers.

Hawker 800, Citation Excel, Learjet 60 or similar


2h 0m

8

5


$ 20,220USD
total for up to 8 travelers
Customize & Book

Book private charter flights from Chicago, IL to Winnipeg, MB. Choose the most convenient airport serving the Winnipeg area, including Winnipeg / James Armstrong Richardson International Airport (CYWG), and Gimli Industrial Park Airport (CYGM). Pick the private plane best suited for your itinerary: from small piston engine planes, to turboprops, to light jets, midsize, large cabin, and ultra-long range business jets.

Linear Air offers air charter flights to destinations around the world, with a wide range of private planes and business jets available for flights when you want them.

How much does a private flight from Chicago to Winnipeg cost?

The total private charter cost between Chicago to Winnipeg ranges from $15824 to $20220 for the specified travel dates. The total fare price for the entire charter plane (price per person is based on the number of passengers entered above).

What are Winnipeg's surrounding cities and towns?

Brooklands
Assiniboia
City Centre
Lord Selkirk - West Kildonan
East Kildonan
Headingley
East Kildonan - Transcona
Oak Bluff
Riel

How long does a flight from Chicago to Winnipeg take?

Flight time depends on the aircraft class and model you choose from among single-engine or twin-engine propeller planes, turboprops, and private jets.

The flight distance from Chicago to Winnipeg is 615 miles and flight time ranges from 2h 0m to 3h 34m, based on plane type. If you were to drive from Chicago to Winnipeg, it would take 16 hours 58 minutes to drive 849 miles.

Popular Charter Flights for Airports Near Winnipeg

Easy Booking with Linear Air

1. FIND YOUR AIRPORTS

Simply enter your flight search above for destinations in the U.S., Canada, Mexico, Bermuda, the Caribbean and Europe. For more help on flight searches, please see How It Works. Air taxis fly to 10x more airports than airlines. Your search will help you find the closest one to you!

2. SELECT YOUR PLANE

Once you've searched above, select your flight. Choose your aircraft type: luxury jet, business-class turbo-prop, or affordable air taxi: based on number of seats, speed, and non-stop range. And the entire plane is yours!

3. SHARE SEATS & SAVE

Share extra seats and receive credit for future plane or jet rental. Simply enter your flight search above, select your flight, continue your purchase, and, as you enter your Billing Address, simply check "I would like to share my extra seat!"

Frequently Asked Questions: Private Flights from Chicago to Winnipeg

The total private charter flight cost from Chicago to Winnipeg ranges from $15,824 to $20,220 for the entire aircraft.
Large Air Taxi: $15,824
Light Jet: $16,630
Personal Jet: $16,931
Executive Air Taxi: $17,932
Midsize Jet: $20,220
Flight time depends on the aircraft class you choose from among single-engine or twin-engine propeller planes, turboprops and business jets. The flight distance from Chicago to Winnipeg is 849 miles and flight time ranges from 2h 0m to 3h 34m, based on type of plane. If you were to drive from Chicago to Winnipeg it would take 16 hours 58 minutes to drive 849 miles.
Large Air Taxi: 3h 34m
Light Jet: 2h 0m
Personal Jet: 2h 5m
Executive Air Taxi: 2h 48m
Midsize Jet: 2h 0m
Fly to Winnipeg to visit the following cities or towns:
Calgary Tower
Lake Agnes Tea House
Magnetawan Inn Restaurant
Oka Sushi
Le Jardin
Oregano Ristorante
Bistro 96 Wine Bar
Barbizon
Rosewood Bistro
Marlowe Restaurant
Napanee Golf Course
Playland at the PNE
University of Lethbridge
Canadian University College
University of Alberta
Mount Royal University
University of Windsor
University of Waterloo
McMaster University
University of Toronto
University of British Columbia Okanagan
University of Ottawa
Chicago to Winnipeg Private Flights