Question 1

How long does a flight from Chicago to Winnipeg take?

Accepted Answer

Direct flights cover the 720 miles separating Chicago to Winnipeg in about 2h 38m.

Question 2

How many flights are there between Chicago and Winnipeg per day?

Accepted Answer

Each day, there are 2 nonstop flights that take off from Chicago and land in Winnipeg, with an average flight time of 2h 38m. The most common departure time is 7:00 pm and most flights take off in the morning. Each week, there are 14 flights and there are the same amount of flights each day (2).

Question 3

How many flights are there between Chicago and Winnipeg per day?

Accepted Answer

Each day, there are 2 nonstop flights that take off from Chicago and land in Winnipeg, with an average flight time of 2h 38m. The most common departure time is 7:00 pm and most flights take off in the morning. Each week, there are 14 flights and there are the same amount of flights each day (2).

Question 4

What is the cheapest flight from Chicago to Winnipeg?

Accepted Answer

In the last 5 days, the lowest price for a flight from Chicago to Winnipeg was $148 for a one-way ticket and $337 for a round-trip.

Question 5

Do I need a passport to fly between Chicago and Winnipeg?

Accepted Answer

Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Winnipeg.

Question 6

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

Accepted Answer

If you are looking for a flight deal from Chicago to Winnipeg, look for departures on Tuesdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Winnipeg, Saturday is the cheapest day to fly and Tuesday is the most expensive.

Question 7

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

Accepted Answer

If you are looking for a flight deal from Chicago to Winnipeg, look for departures on Tuesdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Winnipeg, Saturday is the cheapest day to fly and Tuesday is the most expensive.

Question 8

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

Accepted Answer

On your way to Winnipeg, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Winnipeg.

Question 9

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

Accepted Answer

Early birds can take the earliest flight from Chicago at 9:14 am and will be landing in Winnipeg at 11:52 am.

Question 10

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

Accepted Answer

If you prefer to fly at night, the latest flight from Chicago to Winnipeg jets off at 8:00 pm and lands at 10:38 pm.

Question 11

Which airlines fly non-stop between Chicago and Winnipeg?

Accepted Answer

There is just one airline that flies from Chicago to Winnipeg direct and that is United Airlines. The best round-trip deal found from United Airlines for the route is $362.

Question 12

Which airlines fly non-stop between Chicago and Winnipeg?

Accepted Answer

There is just one airline that flies from Chicago to Winnipeg direct and that is United Airlines. The best round-trip deal found from United Airlines for the route is $362.

Question 13

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

Accepted Answer

Only Cathay Pacific offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

Question 14

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 15

Which airline alliances offer flights from Chicago to Winnipeg?

Accepted Answer

Star Alliance is the only airline alliance operating flights between Chicago and Winnipeg.

Question 16

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

Accepted Answer

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

Question 17

What is the cheapest month to fly from Chicago to Winnipeg?

Accepted Answer

The cheapest month for flights from Chicago to Winnipeg is September, where tickets cost $435 (return) on average. On the other hand, the most expensive months are January and May, where the average cost of round-trip tickets is $1,231 and $863 respectively.

Question 18

What is the cheapest month to fly from Chicago to Winnipeg?

Accepted Answer

The cheapest month for flights from Chicago to Winnipeg is September, where tickets cost $435 (return) on average. On the other hand, the most expensive months are January and May, where the average cost of round-trip tickets is $1,231 and $863 respectively.

Question 19

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.

Question 20

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 travelers know whether to wait or book now.

Question 21

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.

Question 22

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.

Question 23

What is the cheapest layover airport when flying from Chicago to Winnipeg?

Accepted Answer

Flights via Calgary (YYC) offer the most affordable fares, with an average round-trip price of $443.

Question 24

What is the most popular layover airport when flying from Chicago to Winnipeg?

Accepted Answer

Minneapolis (MSP) is the top choice – 48% of KAYAK users who clicked on 1-stop flights from Chicago to Winnipeg picked an itinerary connecting there.

Question 25

Which layover airport has the quickest connection when flying from Chicago to Winnipeg?

Accepted Answer

If you prefer a quick connection, Minneapolis (MSP) often has the shortest layovers from Chicago to Winnipeg, with an average of 1h 21m.

Question 26

Which layover airport offers the shortest total travel time from Chicago to Winnipeg?

Accepted Answer

Consider flying via Minneapolis (MSP) for the shortest journey. The average one-way travel time for flights connecting there is 4h 40m.

Question 27

Which cabin class options are there for flights between Chicago 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 28

Which cabin class options are there for flights between Chicago 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 29

Which airlines provide the cheapest flights from Chicago to Winnipeg?

Accepted Answer

In the past 5 days, the cheapest round-trip tickets from Chicago to Winnipeg were found on WestJet ($389) and Porter Airlines ($478).

Question 30

Which airlines provide the cheapest flights from Chicago to Winnipeg?

Accepted Answer

In the past 5 days, the cheapest round-trip tickets from Chicago to Winnipeg were found on WestJet ($389) and Porter Airlines ($478).

Question 31

What is the cheapest Chicago to Winnipeg flight route?

Accepted Answer

The cheapest return flight from Chicago to Winnipeg costs $1,042 on the route between Chicago O'Hare Intl Airport (ORD) and Winnipeg (YWG). It is also the most popular route.

Question 32

What is the cheapest Chicago to Winnipeg flight route?

Accepted Answer

The cheapest return flight from Chicago to Winnipeg costs $1,042 on the route between Chicago O'Hare Intl Airport (ORD) and Winnipeg (YWG). It is also the most popular route.

Question 33

Can I save money by flying with a layover from Chicago 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 $696 on average.

Question 34

Can I save money by flying with a layover from Chicago 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 $696 on average.

Question 35

What are the most popular airlines flying to Winnipeg?

Accepted Answer

The most popular airline among KAYAK users flying to Winnipeg is United Airlines, followed by WestJet.

Low season	September
High season	May
Cheapest flight	$148

CHI - YWG

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Everything you should know

Cheap Flights from Chicago to Winnipeg (CHI-YWG)

Recent round-trip flight deals from Chicago to Winnipeg

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KAYAK's insights & trends for Chicago to Winnipeg flights

What is the cheapest Chicago to Winnipeg flight route?

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

What is the cheapest month to fly from Chicago to Winnipeg?

Can I save money by flying with a layover from Chicago to Winnipeg?

Which airlines provide the cheapest flights from Chicago to Winnipeg?

Which airlines fly non-stop between Chicago and Winnipeg?

What is the most popular layover airport when flying from Chicago to Winnipeg?

What is the cheapest layover airport when flying from Chicago to Winnipeg?

Which layover airport offers the shortest total travel time from Chicago to Winnipeg?

Which layover airport has the quickest connection when flying from Chicago to Winnipeg?

Which cabin class options are there for flights between Chicago and Winnipeg?

How many flights are there between Chicago and Winnipeg per day?

How long does a flight from Chicago to Winnipeg take?

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

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

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