Question 1

How long does a flight from Chicago to Winnipeg take?

Accepted Answer

A direct flight to Winnipeg will take on average 2h 24m to travel the 1,829 km flying distance from Chicago. Visit our flight page for the latest deals!>/a>

Question 2

How many flights are there between Chicago O'Hare Intl Airport and Winnipeg per day?

Accepted Answer

There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Winnipeg, with an average flight time of 2h 35m. The most common departure time is 9:00 a.m. and most flights take off in the morning. Each week, there are 7 flights. Visit our flight page for the latest deals!>/a>

Question 3

How many flights are there between Chicago O'Hare Intl Airport and Winnipeg per day?

Accepted Answer

There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Winnipeg, with an average flight time of 2h 35m. The most common departure time is 9:00 a.m. and most flights take off in the morning. Each week, there are 7 flights. Visit our flight page for the latest deals!>/a>

Question 4

What is the cheapest flight from Chicago O'Hare Intl Airport to Winnipeg?

Accepted Answer

In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was C$ 111 for a one-way ticket and C$ 299 for a round-trip. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Winnipeg-YWG'>Visit our flight page for the latest deals!>/a>

Question 5

What’s the cheapest day of the week to fly from Chicago to Winnipeg?

Accepted Answer

If your flying dates are flexible, you should consider flying to Winnipeg on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Chicago to Winnipeg. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals. Visit our flight page for the latest deals!>/a>

Question 6

What’s the cheapest day of the week to fly from Chicago to Winnipeg?

Accepted Answer

If your flying dates are flexible, you should consider flying to Winnipeg on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Chicago to Winnipeg. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals. Visit our flight page for the latest deals!>/a>

Question 7

Which airports will I be using when flying from Chicago to Winnipeg?

Accepted Answer

Chicago airport is called Chicago O'Hare Intl and the only airport in Winnipeg is Winnipeg. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Winnipeg-YWG'>Visit our flight page for the latest deals!>/a>

Question 8

What’s the earliest departure time from Chicago to Winnipeg?

Accepted Answer

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 9:22 am and will be landing in Winnipeg at 11:57 am.

Question 9

What’s the latest departure time from Chicago to Winnipeg?

Accepted Answer

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Winnipeg jets off at 9:22 am and lands at 11:57 am.

Question 10

Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?

Accepted Answer

Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

Question 11

Which aircraft models fly most regularly from Chicago to Winnipeg?

Accepted Answer

The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Winnipeg flight route.

Question 12

On which days can I fly direct from Chicago to Winnipeg?

Accepted Answer

There are direct flights from Chicago to Winnipeg on a daily basis.

Question 13

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?

Accepted Answer

The cheapest month for flights from Chicago O'Hare Intl Airport to Winnipeg is May, where tickets cost C$ 323 (return) on average. On the other hand, the most expensive months are November and July, where the average cost of round-trip tickets is C$ 1,060 and C$ 985 respectively.

Question 14

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?

Accepted Answer

The cheapest month for flights from Chicago O'Hare Intl Airport to Winnipeg is May, where tickets cost C$ 323 (return) on average. On the other hand, the most expensive months are November and July, where the average cost of round-trip tickets is C$ 1,060 and C$ 985 respectively.

Question 15

How does KAYAK find such low prices on flights from Chicago to Winnipeg?

Accepted Answer

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Winnipeg. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Winnipeg-YWG'>Visit our flight page for the latest deals!>/a>

Question 16

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Winnipeg?

Accepted Answer

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago is likely to change within 7 days, so travellers know whether to wait or book now. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Winnipeg-YWG'>Visit our flight page for the latest deals!>/a>

Question 17

What is the Hacker Fare option on flights from Chicago to Winnipeg?

Accepted Answer

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago with another airline. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Winnipeg-YWG'>Visit our flight page for the latest deals!>/a>

Question 18

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Winnipeg?

Accepted Answer

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Winnipeg-YWG'>Visit our flight page for the latest deals!>/a>

Question 19

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Winnipeg?

Accepted Answer

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 20

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Winnipeg?

Accepted Answer

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 21

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Winnipeg?

Accepted Answer

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 422 on average.

Question 22

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Winnipeg?

Accepted Answer

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 422 on average.

Low season	January
High season	July
Cheapest flight	C$ 111

ORD - YWG

C$ 111 Find Cheap Flights from Chicago to Winnipeg

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KAYAK's insights & trends for Chicago to Winnipeg flights

Get data-powered insights and trends into flights from Chicago to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Winnipeg?

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?

The cheapest month for flights from Chicago O'Hare Intl Airport to Winnipeg is May, where tickets cost C$ 323 (return) on average. On the other hand, the most expensive months are November and July, where the average cost of round-trip tickets is C$ 1,060 and C$ 985 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Winnipeg?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 422 on average.

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Winnipeg?

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How many flights are there between Chicago O'Hare Intl Airport and Winnipeg per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Winnipeg, with an average flight time of 2h 35m. The most common departure time is 9:00 a.m. and most flights take off in the morning. Each week, there are 7 flights.

How long does a flight from Chicago to Winnipeg take?

A direct flight to Winnipeg will take on average 2h 24m to travel the 1,829 km flying distance from Chicago.

What’s the earliest departure time from Chicago to Winnipeg?

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 9:22 am and will be landing in Winnipeg at 11:57 am.

What’s the latest departure time from Chicago to Winnipeg?

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Winnipeg jets off at 9:22 am and lands at 11:57 am.

Expert advice for your flight from Chicago to Winnipeg

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When to book flights from Chicago to Winnipeg

FAQs for booking Chicago to Winnipeg flights

What is the cheapest flight from Chicago O'Hare Intl Airport to Winnipeg?

In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Winnipeg was C$ 111 for a one-way ticket and C$ 299 for a round-trip.

Which airports will I be using when flying from Chicago to Winnipeg?

Chicago airport is called Chicago O'Hare Intl and the only airport in Winnipeg is Winnipeg.

Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?

Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

Which aircraft models fly most regularly from Chicago to Winnipeg?

The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Winnipeg flight route.

On which days can I fly direct from Chicago to Winnipeg?

There are direct flights from Chicago to Winnipeg on a daily basis.

How does KAYAK find such low prices on flights from Chicago to Winnipeg?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Winnipeg.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Winnipeg?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

What is the Hacker Fare option on flights from Chicago to Winnipeg?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Winnipeg?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Chicago to Winnipeg?

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