How does KAYAK find such low prices on flights from Illinois 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 Illinois to Winnipeg.

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

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

What is the Hacker Fare option on flights from Illinois 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 Illinois with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois 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 Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$145 CHEAP FLIGHTS from Illinois to Winnipeg

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Cheap Flights from Illinois to Winnipeg

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Illinois to Winnipeg

Thu, Oct 15 - Mon, Oct 19

5:30 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

$316WestJet

Sun, Oct 11 - Sun, Oct 18

5:30 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

$327WestJet

Sun, Oct 11 - Sun, Oct 18

5:30 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

$333WestJet

Fri, Oct 9 - Mon, Oct 12

3:20 pm - 9:45 amMDW Chicago Midway-YWG Winnipeg

18h 25m1 stop Toronto Island

7:45 am - 11:00 amYWG Winnipeg-MDW Chicago Midway

27h 15m1 stop Toronto Pearson Intl

$345Multiple Airlines

Fri, Oct 2 - Mon, Oct 5

5:30 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

7:45 am - 3:20 pmYWG Winnipeg-ORD Chicago O'Hare Intl

31h 35m2 stops Toronto Pearson Intl Fort Lauderdale

$350Multiple Airlines

Fri, Oct 2 - Wed, Oct 7

5:30 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

7h 25m1 stop Calgary

10:10 am - 5:17 amYWG Winnipeg-ORD Chicago O'Hare Intl

19h 07m2 stops Calgary Las Vegas Harry Reid Intl

$354Multiple Airlines

Fri, Oct 30 - Fri, Nov 6

6:21 am - 11:48 amSTL Lambert-St Louis-YWG Winnipeg

5h 27m1 stop Minneapolis St Paul

5:40 pm - 11:21 pmYWG Winnipeg-STL Lambert-St Louis

5h 41m1 stop Minneapolis St Paul

$729Delta

Fri, Nov 13 - Sat, Nov 21

6:13 am - 12:00 pmSTL Lambert-St Louis-YWG Winnipeg

5h 47m1 stop Minneapolis St Paul

5:32 pm - 11:18 pmYWG Winnipeg-STL Lambert-St Louis

5h 46m1 stop Minneapolis St Paul

$767Delta

Fri, Oct 2 - Tue, Oct 6

1:55 pm - 11:47 pmORD Chicago O'Hare Intl-YWG Winnipeg

9h 52m2 stops Boston Logan Intl Toronto Pearson Intl

2:05 pm - 7:59 amYWG Winnipeg-ORD Chicago O'Hare Intl

17h 54m2 stops Toronto Pearson Intl Boston Logan Intl

$816United Airlines

Wed, Dec 23 - Sun, Jan 10

6:00 pm - 2:09 pmORD Chicago O'Hare Intl-YWG Winnipeg

20h 09m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl

2:40 pm - 9:09 amYWG Winnipeg-ORD Chicago O'Hare Intl

18h 29m2 stops Toronto Pearson Intl New York LaGuardia

$867United Airlines

Recent last minute flight deals from Illinois to Winnipeg

Mon, Sep 21 - Wed, Sep 23

8:30 pm - 3:19 pmORD Chicago O'Hare Intl-YWG Winnipeg

18h 49m1 stop Toronto Pearson Intl

9:20 am - 4:18 pmYWG Winnipeg-ORD Chicago O'Hare Intl

6h 58m1 stop Toronto Pearson Intl

$871Porter Airlines

Mon, Sep 21 - Tue, Sep 22

7:20 am - 12:35 amORD Chicago O'Hare Intl-YWG Winnipeg

17h 15m2 stops San Diego Las Vegas Harry Reid Intl

7:00 am - 4:40 pmYWG Winnipeg-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

$884Multiple Airlines

Mon, Sep 21 - Tue, Sep 22

8:30 pm - 3:19 pmORD Chicago O'Hare Intl-YWG Winnipeg

18h 49m1 stop Toronto Pearson Intl

8:45 pm - 7:40 amYWG Winnipeg-ORD Chicago O'Hare Intl

10h 55m1 stop Toronto Pearson Intl

$896Porter Airlines

Fri, Sep 18 - Mon, Sep 21

6:10 am - 9:40 pmORD Chicago O'Hare Intl-YWG Winnipeg

15h 30m2 stops Minneapolis St Paul Edmonton

6:00 am - 9:33 pmYWG Winnipeg-ORD Chicago O'Hare Intl

15h 33m2 stops Calgary Minneapolis St Paul

$1,273WestJet

Fri, Sep 18 - Mon, Sep 21

1:55 pm - 12:55 amORD Chicago O'Hare Intl-YWG Winnipeg

11h 00m2 stops Detroit Metropolitan Wayne County Calgary

7:00 am - 9:33 pmYWG Winnipeg-ORD Chicago O'Hare Intl

14h 33m2 stops Calgary Minneapolis St Paul

$1,454WestJet

Fri, Sep 18 - Mon, Sep 21

7:13 pm - 11:30 pmMDW Chicago Midway-YWG Winnipeg

4h 17m1 stop Minneapolis St Paul

7:10 pm - 4:15 pmYWG Winnipeg-MDW Chicago Midway

21h 05m2 stops Calgary Atlanta Hartsfield-Jackson

$1,457WestJet

Fri, Sep 18 - Mon, Sep 21

9:15 am - 11:52 amORD Chicago O'Hare Intl-YWG Winnipeg

2h 37mnonstop

7:00 am - 9:35 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$1,515United Airlines

Fri, Sep 18 - Mon, Sep 21

7:13 pm - 11:30 pmMDW Chicago Midway-YWG Winnipeg

4h 17m1 stop Minneapolis St Paul

12:41 pm - 10:44 pmYWG Winnipeg-MDW Chicago Midway

10h 03m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

$1,518Delta

Fri, Sep 18 - Mon, Sep 21

2:32 pm - 8:57 pmORD Chicago O'Hare Intl-YWG Winnipeg

6h 25m1 stop Denver Intl

7:00 am - 9:35 amYWG Winnipeg-ORD Chicago O'Hare Intl

2h 35mnonstop

$1,525United Airlines

Fri, Sep 18 - Mon, Sep 21

7:13 pm - 11:30 pmMDW Chicago Midway-YWG Winnipeg

4h 17m1 stop Minneapolis St Paul

12:41 pm - 6:19 pmYWG Winnipeg-MDW Chicago Midway

5h 38m1 stop Minneapolis St Paul

$1,740Delta

Useful Info

Low season	January
High season	August
Cheapest flight	$145

Best time to beat the crowds with an average 21% drop in price.

Most popular time to fly with an average 11% increase in price.

Flight from Chicago Midway Airport to Winnipeg

How does KAYAK find such low prices on flights from Illinois 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 Illinois to Winnipeg.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Winnipeg?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Illinois is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Illinois 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 Illinois with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois 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 Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.