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Cheap flights from Winnipeg to Chicago from $137

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago departing on 1/29. 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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Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Winnipeg to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Winnipeg to Chicago.

Cheap last minute flights

Planning a quick getaway from Winnipeg to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Winnipeg to Chicago

Find recent round-trip train or bus tickets from Winnipeg to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:35 am - 9:37 amYWG-ORD
22h 02m2 stops
5:00 am - 7:10 pmORD-YWG
14h 10m2 stops
Mon, Dec 9 - Tue, Dec 17
12:30 pm - 4:44 pmYWG-ORD
28h 14m1 stop
5:30 pm - 11:01 pmORD-YWG
29h 31m1 stop
$343WestJet
Find Deal
Wed, May 7 - Wed, May 14
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$358Air Canada
Find Deal
Fri, Jan 31 - Tue, Apr 22
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
10:40 am - 5:18 pmORD-YWG
6h 38m1 stop
$364Air Canada
Find Deal
Sun, Jan 26 - Sat, Apr 26
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
5:00 am - 1:03 pmORD-YWG
8h 03m1 stop
$419United Airlines
Find Deal
Wed, Jan 29 - Sun, Apr 20
2:15 pm - 4:37 pmYWG-ORD
2h 22mnonstop
5:00 am - 1:27 pmORD-YWG
8h 27m1 stop
$421United Airlines
Find Deal
Wed, Mar 26 - Sat, Mar 29
12:45 pm - 10:20 pmYWG-MDW
9h 35m2 stops
9:20 am - 4:53 pmMDW-YWG
7h 33m1 stop
$425Delta
Find Deal
Thu, Jan 30 - Sat, Apr 26
6:55 am - 1:31 pmYWG-MDW
6h 36m1 stop
4:50 pm - 11:43 pmMDW-YWG
6h 53m1 stop
$470Delta
Find Deal
Wed, Dec 18 - Wed, Dec 25
6:45 pm - 12:00 pmYWG-MDW
17h 15m1 stop
5:35 pm - 10:45 amMDW-YWG
17h 10m1 stop
$545Porter Airlines
Find Deal
Fri, Dec 6 - Mon, Dec 9
11:35 am - 10:30 amYWG-MDW
22h 55m2 stops
5:35 pm - 10:45 amMDW-YWG
17h 10m1 stop
$546Porter Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
7:30 am - 7:06 pmYWG-MDW
11h 36m1 stop
Wed, Jan 29
7:30 am - 5:57 pmYWG-MDW
10h 27m1 stop
Wed, Jan 15
7:45 am - 2:45 pmYWG-ORD
7h 00m1 stop
$203Air Canada
Find Deal
Wed, Jan 29
7:30 am - 1:11 pmYWG-ORD
5h 41m1 stop
$209Air Canada
Find Deal
Wed, Jan 15
6:55 am - 11:59 pmYWG-ORD
17h 04m2 stops
$213Delta
Find Deal
Tue, Jan 14
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$228United Airlines
Find Deal
Thu, Jan 9
6:55 am - 6:14 pmYWG-MDW
11h 19m2 stops
$240Delta
Find Deal
Tue, Jan 14
4:30 pm - 11:10 pmYWG-ORD
6h 40m1 stop
$243United Airlines
Find Deal
Thu, Dec 19
6:00 am - 9:58 pmYWG-ORD
15h 58m2 stops
$279WestJet
Find Deal
Wed, Jan 29
8:00 pm - 6:32 pmYWG-MDW
22h 32m2 stops
$286WestJet
Find Deal
Tue, Dec 3
11:35 am - 6:31 pmYWG-ORD
30h 56m3 stops
7:39 pm - 7:02 pmORD-YWG
23h 23m2 stops
Fri, Nov 22 - Sun, Nov 24
4:00 pm - 8:03 pmYWG-ORD
28h 03m2 stops
7:39 pm - 7:02 pmORD-YWG
23h 23m2 stops
Fri, Nov 22 - Sun, Nov 24
8:30 am - 5:09 pmYWG-ORD
8h 39m1 stop
9:14 pm - 8:28 amORD-YWG
11h 14m1 stop
$917Air Canada
Find Deal
Fri, Nov 22 - Mon, Nov 25
4:00 pm - 10:56 amYWG-ORD
18h 56m1 stop
7:39 pm - 7:02 pmORD-YWG
23h 23m2 stops
Fri, Nov 22 - Sun, Nov 24
11:35 am - 6:31 pmYWG-ORD
30h 56m3 stops
8:58 pm - 8:11 amORD-YWG
35h 13m3 stops
Fri, Nov 22 - Sun, Nov 24
8:45 am - 10:43 pmYWG-ORD
13h 58m2 stops
3:45 pm - 11:26 amORD-YWG
19h 41m2 stops
$1,021WestJet
Find Deal
Fri, Nov 22 - Mon, Nov 25
7:30 am - 2:25 pmYWG-ORD
6h 55m1 stop
7:05 am - 4:55 pmORD-YWG
9h 50m2 stops
$1,053Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
5:45 pm - 1:37 pmYWG-MDW
19h 52m1 stop
7:17 pm - 11:41 amMDW-YWG
16h 24m1 stop
$1,079WestJet
Find Deal
Fri, Nov 22 - Mon, Nov 25
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$1,114United Airlines
Find Deal
Fri, Nov 22 - Sun, Nov 24
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$1,487Air Canada
Find Deal
Fri, Nov 22 - Mon, Nov 25
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$358Air Canada
Find Deal
Fri, Jan 31 - Sat, Apr 26
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$389Air Canada
Find Deal
Wed, Apr 23 - Wed, Apr 30
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
Wed, Jan 29 - Wed, Apr 23
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$420Air Canada
Find Deal
Tue, Apr 1 - Tue, Apr 8
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$424Air Canada
Find Deal
Tue, Jan 21 - Tue, Jan 28
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
$430United Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
2:15 pm - 4:36 pmYWG-ORD
2h 21mnonstop
1:00 pm - 3:24 pmORD-YWG
2h 24mnonstop
$444United Airlines
Find Deal
Sat, Apr 5 - Sun, Apr 13
2:15 pm - 4:37 pmYWG-ORD
2h 22mnonstop
12:58 pm - 3:28 pmORD-YWG
2h 30mnonstop
$456United Airlines
Find Deal
Wed, Mar 26 - Sat, Mar 29
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$487Air Canada
Find Deal
Wed, Dec 4 - Wed, Dec 11
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
$489Air Canada
Find Deal
Fri, Dec 6 - Tue, Dec 10

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
May 7
YWG12:30 pmWinnipeg
28h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
May 14
ORD5:30 pmChicago O'Hare Intl
29h 31m
1 stop
YWG11:01 pmWinnipeg
WestJet
Jan 29
YWG5:37 pmWinnipeg
24h 10m
1 stop
MDW5:47 pmChicago Midway
Apr 23
MDW9:30 amChicago Midway
15h 04m
2 stops
YWG12:34 amWinnipeg
WestJet
May 7
YWG12:30 pmWinnipeg
28h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
May 14
ORD7:00 amChicago O'Hare Intl
8h 58m
2 stops
YWG3:58 pmWinnipeg

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets
Air Canada
Jan 31
YWG7:45 amWinnipeg
7h 00m
1 stop
ORD2:45 pmChicago O'Hare Intl
Apr 22
ORD1:00 pmChicago O'Hare Intl
2h 24m
YWG3:24 pmWinnipeg
Air Canada
Jan 26
YWG7:45 amWinnipeg
7h 00m
1 stop
ORD2:45 pmChicago O'Hare Intl
Apr 26
ORD10:40 amChicago O'Hare Intl
6h 38m
1 stop
YWG5:18 pmWinnipeg
Air Canada
Apr 23
YWG7:45 amWinnipeg
7h 09m
1 stop
ORD2:54 pmChicago O'Hare Intl
Apr 30
ORD7:20 amChicago O'Hare Intl
9h 04m
1 stop
YWG4:24 pmWinnipeg

See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago

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 from Winnipeg to Chicago?

June. The cheapest time of year to fly to Chicago from Winnipeg is June. Most expensive is January

What is the cheapest day to depart Winnipeg for Chicago?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday

When is the cheapest time to fly from Winnipeg to Chicago?

In the afternoon. Winnipeg to Chicago flights are approximately 4% more expensive at noon than in the afternoon

What is the cheapest Winnipeg to Chicago flight route?

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

How far in advance should you book Winnipeg to Chicago flights?

14 days before. The cheapest time to buy a flight from Winnipeg to Chicago is approximately 14 days to departure

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

There are 2 cabin classes available to choose from on Winnipeg to Chicago 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 Winnipeg to Chicago flights?

You could potentially save up to 32% on your flight if you consider stops on a Winnipeg to Chicago flight.

How have Winnipeg to Chicago flight prices changed over time?

As of November 2024, prices for Winnipeg to Chicago flights are approximately 17% more expensive when compared to flights at the same time last year.

When to book flights from Winnipeg to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips

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

Best Price Found

$137

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $137. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $338.
The fastest flight from Winnipeg to Chicago takes 2h 21m
Direct flights go from Winnipeg to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Winnipeg to Chicago by plane?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 2h 21m.

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

    Prices for flights from Winnipeg Airport to Chicago are refreshed on a daily basis.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Winnipeg Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

  • What is the most popular airline from Winnipeg to Chicago?


Best airlines flying from Winnipeg to Chicago

Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $289Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
DeltaPriceFrom $370Free CancellationRating
8.0
8,756 reviews
Search Delta flights
United AirlinesPriceFrom $441Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $441 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $533 round-trip - but some users have found much cheaper deals with momondo.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.0/10 from 8,237 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around $550, with deals from around $289 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.


Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Winnipeg.

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

momondo does allow users to show only those flights to Chicago from Winnipeg which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Chicago from Winnipeg. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Winnipeg are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago