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Cheap flights from Winnipeg to Chicago from $197

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:35 pm - 12:10 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
15h 35m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:33 pm - 2:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
24h 07m1 stop Atlanta Hartsfield-Jackson
$402Multiple Airlines
Wed, Jan 6 - Tue, Jan 19
Multiple Airlines Logo
7:00 am - 11:23 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
17h 23m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 1:10 amORD  Chicago O'Hare Intl-YWG Winnipeg
18h 10m2 stops Atlanta Hartsfield-Jackson Calgary
$412Multiple Airlines
Fri, Jan 22 - Thu, Feb 4
Multiple Airlines Logo
9:35 pm - 12:10 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
15h 35m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 2:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
7h 40m1 stop Atlanta Hartsfield-Jackson
$413Multiple Airlines
Wed, Jan 6 - Fri, Jan 22
Multiple Airlines Logo
9:35 pm - 12:10 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
15h 35m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:00 am - 2:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
7h 40m1 stop Atlanta Hartsfield-Jackson
$413Multiple Airlines
Wed, Jan 6 - Mon, Jan 18
Air Canada Logo
8:15 am - 3:38 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
8h 23m1 stop Toronto Pearson Intl
Air Canada Logo
9:00 am - 10:24 pmORD  Chicago O'Hare Intl-YWG Winnipeg
12h 24m2 stops Newark Toronto Pearson Intl
$659Air Canada
Sat, Jan 9 - Sat, Jan 23
Air Canada Logo
6:15 am - 1:13 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
7h 58m1 stop Toronto Pearson Intl
Air Canada Logo
7:01 am - 3:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
7h 08m1 stop Toronto Pearson Intl
$667Air Canada
Thu, Jan 14 - Fri, Jan 15
United Airlines Logo
8:00 am - 9:45 amYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 45mnonstop
United Airlines Logo
3:50 pm - 7:28 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 38mnonstop
$673United Airlines
Thu, Jan 7 - Sat, Jan 23
United Airlines Logo
8:00 am - 9:45 amYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 45mnonstop
United Airlines Logo
3:50 pm - 7:28 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 38mnonstop
$673United Airlines
Tue, Jan 5 - Sun, Jan 17
United Airlines Logo
8:00 am - 9:45 amYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 45mnonstop
United Airlines Logo
3:50 pm - 7:28 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 38mnonstop
$673United Airlines
Tue, Jan 5 - Tue, Jan 19
Air Canada Logo
2:15 pm - 4:36 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 21mnonstop
Air Canada Logo
9:15 am - 11:39 amORD  Chicago O'Hare Intl-YWG Winnipeg
2h 24mnonstop
$690Air Canada
Mon, Apr 26 - Mon, May 3

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WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
Dec 3
YWG12:22 pmWinnipeg
5h 21m
1 stop
ORD4:43 pmChicago O'Hare Intl
Dec 10
ORD6:20 amChicago O'Hare Intl
4h 11m
1 stop
YWG11:31 amWinnipeg
$465
WestJet
Apr 26
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 3
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$470
WestJet
Apr 26
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 3
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$485

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets
Porter Airlines
Nov 20
YWG7:00 amWinnipeg
8h 36m
1 stop
ORD2:36 pmChicago O'Hare Intl
Nov 27
ORD2:50 pmChicago O'Hare Intl
7h 02m
1 stop
YWG10:52 pmWinnipeg
$640
Porter Airlines
Nov 20
YWG7:00 amWinnipeg
8h 36m
1 stop
ORD2:36 pmChicago O'Hare Intl
Nov 27
ORD2:50 pmChicago O'Hare Intl
7h 02m
1 stop
YWG10:52 pmWinnipeg
$652
Porter Airlines
Nov 22
YWG7:00 amWinnipeg
7h 10m
1 stop
ORD1:10 pmChicago O'Hare Intl
Nov 27
ORD6:20 pmChicago O'Hare Intl
23h 46m
2 stops
YWG7:06 pmWinnipeg
$666

momondo Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 1/6

9:35 pm-12:10 pm

2 stops15h 35m

Chicago O'Hare Intl

Tue 1/19

1:33 pm-2:40 pm

1 stop24h 07m

$402

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 1/22

7:00 am-11:23 pm

1 stop17h 23m

Chicago O'Hare Intl

Thu 2/4

6:00 am-1:10 am

2 stops18h 10m

$412

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 1/6

9:35 pm-12:10 pm

2 stops15h 35m

Chicago O'Hare Intl

Fri 1/22

6:00 am-2:40 pm

1 stop7h 40m

$413

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 1/6

9:35 pm-12:10 pm

2 stops15h 35m

Chicago O'Hare Intl

Mon 1/18

6:00 am-2:40 pm

1 stop7h 40m

$413

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 1/9

8:15 am-3:38 pm

1 stop8h 23m

Chicago O'Hare Intl

Sat 1/23

9:00 am-10:24 pm

2 stops12h 24m

$659

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 1/14

6:15 am-1:13 pm

1 stop7h 58m

Chicago O'Hare Intl

Fri 1/15

7:01 am-3:09 pm

1 stop7h 08m

$667

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 1/7

8:00 am-9:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Sat 1/23

3:50 pm-7:28 pm

Nonstop2h 38m

$673

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 1/5

8:00 am-9:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Sun 1/17

3:50 pm-7:28 pm

Nonstop2h 38m

$673

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 1/5

8:00 am-9:45 am

Nonstop2h 45m

Chicago O'Hare Intl

Tue 1/19

3:50 pm-7:28 pm

Nonstop2h 38m

$673
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 4/26

2:15 pm-4:36 pm

Nonstop2h 21m

Chicago O'Hare Intl

Mon 5/3

9:15 am-11:39 am

Nonstop2h 24m

$690

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 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 to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $523. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Winnipeg to Chicago during May average around $542.

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

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $609. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $723.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Winnipeg to Chicago during this time can be as low as $673. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $697.

What is the cheapest Winnipeg to Chicago flight route?

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

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

There are 4 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 42% 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 2026, prices for Winnipeg to Chicago flights are approximately 59% 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

$197

Fastest flight time

2h 31m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $197. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $402.
The fastest flight from Winnipeg to Chicago takes 2h 31m
Direct flights go from Winnipeg to Chicago every day.
There are 3 airports in Chicago. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Winnipeg to Chicago

  • How far is Winnipeg to Chicago by plane?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 2h 31m.

  • 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?

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
United AirlinesPriceFrom $517Free CancellationRating
7.3
10,472 reviews
Search United Airlines flights
Air CanadaPriceFrom $629Free CancellationRating
7.1
11,874 reviews
Search Air Canada flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $517 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $702 round-trip - but some users have found much cheaper deals with momondo.

  • Air Canada Flights From Winnipeg to Chicago

    Air Canada (7.1/10 from 11,874 reviews) operates around 7 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around $1,130, with deals from around $629 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Lansing
Benton Harbor
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport