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Cheap flights from Illinois to Winnipeg from $166

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Winnipeg departing on 6/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Illinois to Winnipeg

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:28 pm - 3:09 pm
ORD
-
YWG
22h 41m
1 stop
Multiple Airlines Logo
9:05 pm - 10:44 am
YWG
-
ORD
13h 39m
2 stops
$295Multiple Airlines
Tue, Apr 21 - Tue, May 5
Multiple Airlines Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m
1 stop
Multiple Airlines Logo
8:00 am - 10:36 am
YWG
-
ORD
26h 36m
1 stop
$318Multiple Airlines
Mon, Mar 16 - Mon, Mar 23
WestJet Logo
5:30 pm - 12:15 pm
ORD
-
YWG
18h 45m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$326WestJet
Mon, May 11 - Mon, Jun 1
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
$328WestJet
Fri, Jun 5 - Sun, Jun 7
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
9:05 pm - 2:15 pm
YWG
-
ORD
17h 10m
2 stops
$334Multiple Airlines
Fri, May 1 - Fri, May 15
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m
1 stop
$335WestJet
Wed, Jun 17 - Wed, Jun 24
Multiple Airlines Logo
4:42 pm - 3:09 pm
ORD
-
YWG
22h 27m
1 stop
Multiple Airlines Logo
8:00 am - 10:36 am
YWG
-
ORD
26h 36m
1 stop
$337Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Air Canada Logo
7:30 am - 2:18 pm
STL
-
YWG
6h 48m
1 stop
Air Canada Logo
11:00 am - 8:05 pm
YWG
-
STL
9h 05m
1 stop
$424Air Canada
Thu, May 14 - Wed, May 20
United Airlines Logo
6:25 am - 11:57 am
STL
-
YWG
5h 32m
1 stop
United Airlines Logo
2:00 pm - 9:08 pm
YWG
-
STL
7h 08m
1 stop
$427United Airlines
Sun, Mar 22 - Sun, Mar 29
Air Canada Logo
4:05 pm - 11:54 pm
STL
-
YWG
7h 49m
1 stop
Air Canada Logo
7:00 am - 3:29 pm
YWG
-
STL
8h 29m
1 stop
$428Air Canada
Mon, Mar 2 - Wed, Mar 4

WestJet flights from Illinois to Winnipeg

Our best WestJet deals on Illinois to Winnipeg flight tickets
WestJet
May 11
ORD5:30 pmChicago O'Hare Intl
18h 45m
1 stop
YWG12:15 pmWinnipeg
Jun 1
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$326
WestJet
Jun 5
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
Jun 7
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$328
WestJet
Jun 17
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
Jun 24
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
$335

United Airlines flights from Illinois to Winnipeg

Our best United Airlines deals on Illinois to Winnipeg flight tickets
United Airlines
Mar 22
STL6:25 amLambert-St Louis
5h 32m
1 stop
YWG11:57 amWinnipeg
Mar 29
YWG2:00 pmWinnipeg
7h 08m
1 stop
STL9:08 pmLambert-St Louis
$427
United Airlines
Mar 21
STL6:25 amLambert-St Louis
5h 32m
1 stop
YWG11:57 amWinnipeg
Mar 28
YWG2:20 pmWinnipeg
8h 39m
1 stop
STL10:59 pmLambert-St Louis
$601
United Airlines
Mar 2
STL9:55 amLambert-St Louis
11h 49m
2 stops
YWG9:44 pmWinnipeg
Mar 4
YWG11:05 amWinnipeg
10h 00m
2 stops
STL9:05 pmLambert-St Louis
$789

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 6, 2026.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 4/21

4:28 pm-3:09 pm

1 stop22h 41m

Winnipeg

Tue 5/5

9:05 pm-10:44 am

2 stops13h 39m

$295

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 3/16

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Mon 3/23

8:00 am-10:36 am

1 stop26h 36m

$318

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/11

5:30 pm-12:15 pm

1 stop18h 45m

Winnipeg

Mon 6/1

7:00 am-4:40 pm

1 stop9h 40m

$326

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/5

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sun 6/7

7:00 am-4:40 pm

1 stop9h 40m

$328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/1

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 5/15

9:05 pm-2:15 pm

2 stops17h 10m

$334

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 6/17

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Wed 6/24

8:30 am-4:43 pm

1 stop8h 13m

$335

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 3/5

4:42 pm-3:09 pm

1 stop22h 27m

Winnipeg

Mon 3/9

8:00 am-10:36 am

1 stop26h 36m

$337

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 5/14

7:30 am-2:18 pm

1 stop6h 48m

Winnipeg

Wed 5/20

11:00 am-8:05 pm

1 stop9h 05m

$424

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 3/22

6:25 am-11:57 am

1 stop5h 32m

Winnipeg

Sun 3/29

2:00 pm-9:08 pm

1 stop7h 08m

$427

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 3/2

4:05 pm-11:54 pm

1 stop7h 49m

Winnipeg

Wed 3/4

7:00 am-3:29 pm

1 stop8h 29m

$428

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Winnipeg from

How to get the cheapest flight ticket from Illinois to Winnipeg

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

What is the cheapest month to fly to Winnipeg?

In general, May is the cheapest month to fly from Illinois to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $271. If you’re not able to fly to Winnipeg in May, then August is your next best option. Flight prices from Illinois to Winnipeg during August average around $448.

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

The cheapest day to depart on your flight to Winnipeg is on a Saturday when prices can be found for as low as $584. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $675.

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

The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $543. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $699 on average. Flights to Winnipeg from Illinois in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Illinois to Winnipeg flight route?

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

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

There is only 1 cabin class available to choose from on Illinois to Winnipeg flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Illinois to Winnipeg flights?

You could potentially save up to 71% on your flight if you consider stops on a Illinois to Winnipeg flight.

Cheap Illinois to Winnipeg flight deals and tips

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

Best Price Found

$976

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Winnipeg

1 airport
The best flight deal from Illinois to Winnipeg found on momondo in the last 72 hours is $976
The fastest flight from Illinois to Winnipeg takes 2h 24m
Direct flights go from Illinois to Winnipeg every day.
There is 1 airport in Winnipeg. From Illinois there are direct flights to Winnipeg (YWG).
Search flight deals

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

    Prices for flights from Illinois to Winnipeg Airport refresh daily.

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

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

    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 Illinois to Winnipeg Airport.

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The travel and health documents you'll need for your trip to Winnipeg Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Winnipeg Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Illinois to Winnipeg?

Best airlines flying from Illinois to Winnipeg

Compare and see reviews for airlines that fly from Illinois to Winnipeg with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom $156Free CancellationRating
7.2
3,255 reviews
Search WestJet flights
Air CanadaPriceFrom $230Free CancellationRating
7.1
10,697 reviews
Search Air Canada flights
United AirlinesPriceFrom $263Free CancellationRating
7.4
9,245 reviews
Search United Airlines flights

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Scanterbury
Portage la Prairie
Selkirk
Morden

Why use momondo?

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

Finding the right flight to Winnipeg from Illinois is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Winnipeg quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Illinois to Winnipeg flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Illinois and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Illinois to Winnipeg flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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