What is the cheapest airline that flies from Winnipeg to Illinois?

Delta, Porter Airlines, and WestJet are the most popular carriers operating from Winnipeg to Illinois

How many flights depart from Winnipeg to Illinois on average per day?

8 flights are operational daily from Winnipeg to Illinois as of July 2026. The most popular departure time for this route is 7:00AM, with 62% of flights per day taking off at noon.

How many flights depart from Winnipeg to Illinois on average per week?

The number of flights available between Winnipeg and Illinois is 56 per week as of July 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

When did momondo last update prices for flights from Winnipeg Airport to Illinois?

Prices for flights from Winnipeg Airport to Illinois refresh daily.

How many operators does momondo search for flights from Winnipeg Airport to Illinois?

The number of operators available for flights from Winnipeg Airport to Illinois is 1 as of July 2026.

How old do you have to be to fly from Winnipeg Airport to Illinois?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Illinois.

What documentation or ID do you need to fly to Illinois?

The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$189 Cheap Flights from Winnipeg to Illinois in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$271WestJet

Fri, Oct 2 - Sun, Oct 4

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$275WestJet

Thu, Oct 15 - Sun, Oct 18

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$280WestJet

Thu, Oct 15 - Fri, Oct 16

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$282WestJet

Thu, Sep 10 - Thu, Sep 17

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$289WestJet

Fri, Sep 25 - Mon, Sep 28

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$295WestJet

Sat, Sep 5 - Tue, Sep 8

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$297WestJet

Thu, Sep 10 - Thu, Sep 17

7:00 am - 4:40 pm

YWG

ORD

9h 40m

1 stop

5:30 pm - 12:55 am

ORD

YWG

7h 25m

1 stop

$305WestJet

Thu, Sep 24 - Sun, Sep 27

2:00 pm - 4:35 pm

YWG

ORD

2h 35mnonstop

7:54 pm - 10:33 pm

ORD

YWG

2h 39mnonstop

$674United Airlines

Thu, Sep 10 - Thu, Sep 17

2:00 pm - 4:35 pm

YWG

ORD

2h 35mnonstop

10:00 am - 12:37 pm

ORD

YWG

2h 37mnonstop

$674United Airlines

Wed, Sep 23 - Sat, Sep 26

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WestJet flights from Winnipeg to Illinois

Our best WestJet deals on Winnipeg to Illinois flight tickets

WestJet

Oct 2

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 4

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$271

WestJet

Oct 15

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 18

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$275

WestJet

Oct 15

YWG7:00 amWinnipeg

9h 40m

1 stop

ORD4:40 pmChicago O'Hare Intl

Oct 16

ORD5:30 pmChicago O'Hare Intl

7h 25m

1 stop

YWG12:55 amWinnipeg

$280

Porter Airlines flights from Winnipeg to Illinois

Our best Porter Airlines deals on Winnipeg to Illinois flight tickets

Porter Airlines

Oct 7

YWG9:20 amWinnipeg

6h 59m

1 stop

ORD4:19 pmChicago O'Hare Intl

Oct 14

ORD8:06 amChicago O'Hare Intl

7h 13m

1 stop

YWG3:19 pmWinnipeg

$450

Porter Airlines

Sep 2

YWG9:20 amWinnipeg

6h 59m

1 stop

ORD4:19 pmChicago O'Hare Intl

Sep 9

ORD9:45 amChicago O'Hare Intl

10h 09m

1 stop

YWG7:54 pmWinnipeg

$456

Porter Airlines

Sep 11

YWG4:15 pmWinnipeg

22h 20m

2 stops

MDW2:35 pmChicago Midway

Sep 18

MDW3:20 pmChicago Midway

26h 38m

2 stops

YWG5:58 pmWinnipeg

$532

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 10/2

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 10/4

5:30 pm-12:55 am

1 stop7h 25m

$271

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/15

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 10/18

5:30 pm-12:55 am

1 stop7h 25m

$275

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 10/15

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 10/16

5:30 pm-12:55 am

1 stop7h 25m

$280

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/10

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 9/17

5:30 pm-12:55 am

1 stop7h 25m

$282

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 9/25

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/28

5:30 pm-12:55 am

1 stop7h 25m

$289

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/5

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 9/8

5:30 pm-12:55 am

1 stop7h 25m

$295

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/10

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Thu 9/17

5:30 pm-12:55 am

1 stop7h 25m

$297

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/24

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Sun 9/27

5:30 pm-12:55 am

1 stop7h 25m

$305

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 9/10

2:00 pm-4:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Thu 9/17

7:54 pm-10:33 pm

Nonstop2h 39m

$674

Quickest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 9/23

2:00 pm-4:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 9/26

10:00 am-12:37 pm

Nonstop2h 37m

$674

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Winnipeg to Illinois

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Winnipeg is in September. Flight prices, which tend to average around $379, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $387.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Winnipeg to Illinois is on a Saturday when prices can be found for as low as $605. Flights from Winnipeg to Illinois on a Tuesday will generally be more expensive and average around $786. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Winnipeg to Illinois during this time can be as low as $647. Flights in the morning are often more expensive with an average ticket price of $654.

What is the cheapest Winnipeg to Illinois flight route?

Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Illinois flight prices

What cabin class options are available on Winnipeg to Illinois flights?

There are 4 cabin classes available to choose from on Winnipeg to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Winnipeg to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Illinois

Best Price Found	$361
Fastest flight time	2h 34m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Winnipeg in the past 72 hours is $361. The best round-trip flight deal from Winnipeg to Illinois found on momondo in the last 72 hours is $528.

The fastest flight from Winnipeg to Illinois takes 2h 34m

Direct flights go from Winnipeg to Illinois every day.

There are 98 airports in Illinois. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Winnipeg to Illinois

When did momondo last update prices for flights from Winnipeg Airport to Illinois?
Prices for flights from Winnipeg Airport to Illinois refresh daily.
How many operators does momondo search for flights from Winnipeg Airport to Illinois?
The number of operators available for flights from Winnipeg Airport to Illinois is 1 as of July 2026.
How old do you have to be to fly from Winnipeg Airport to Illinois?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Winnipeg to Illinois?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Winnipeg to Illinois is Embraer 175 (Enhanced Winglets) (81.36% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (6.78%), Boeing 737 MAX 8 (5.08%), and Boeing 737 MAX 9 (1.69%).

Best airlines flying from Winnipeg to Illinois

Compare and see reviews for airlines that fly from Winnipeg to Illinois with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $335	Free Cancellation	Rating 7.4 10,052 reviews		Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Illinois?

It is quick and easy to find Winnipeg to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

Can I find flights from Winnipeg to Illinois with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Illinois from Winnipeg with this policy.

How can momondo help me find flights from Winnipeg to Illinois?

Once all potential Winnipeg to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Winnipeg to Illinois right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Winnipeg to Illinois now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Illinois and let you know when they change.