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Cheap flights from Winnipeg to Chicago from $165

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.
Porter Airlines Logo
11:40 am - 11:40 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
12:20 pm - 9:57 pmORD  Chicago O'Hare Intl-YWG Winnipeg
9h 37m1 stop Toronto Island
$361Porter Airlines
Sat, Nov 7 - Thu, Nov 19
Multiple Airlines Logo
11:40 am - 11:40 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 00m2 stops Ottawa Toronto Island
Multiple Airlines Logo
12:20 pm - 12:44 amORD  Chicago O'Hare Intl-YWG Winnipeg
12h 24m1 stop Toronto Island
$361Multiple Airlines
Sat, Nov 7 - Sun, Nov 22
Multiple Airlines Logo
11:40 am - 11:40 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 00m2 stops Ottawa Toronto Pearson Intl
Multiple Airlines Logo
12:20 pm - 12:44 amORD  Chicago O'Hare Intl-YWG Winnipeg
12h 24m1 stop Toronto Island
$361Multiple Airlines
Sat, Nov 7 - Fri, Nov 20
Porter Airlines Logo
11:40 am - 11:40 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
12:20 pm - 9:57 pmORD  Chicago O'Hare Intl-YWG Winnipeg
9h 37m1 stop Toronto Island
$362Porter Airlines
Sat, Nov 7 - Mon, Nov 23
Porter Airlines Logo
11:40 am - 11:40 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
6:20 pm - 10:45 amORD  Chicago O'Hare Intl-YWG Winnipeg
16h 25m1 stop Toronto Island
$362Porter Airlines
Sat, Nov 7 - Sat, Nov 21
Porter Airlines Logo
7:05 pm - 11:40 amYWG  Winnipeg-ORD Chicago O'Hare Intl
16h 35m1 stop Toronto Pearson Intl
Porter Airlines Logo
12:20 pm - 9:57 pmORD  Chicago O'Hare Intl-YWG Winnipeg
9h 37m1 stop Toronto Island
$365Porter Airlines
Sat, Nov 7 - Thu, Nov 19
Porter Airlines Logo
7:05 pm - 11:40 amYWG  Winnipeg-ORD Chicago O'Hare Intl
16h 35m1 stop Toronto Pearson Intl
Porter Airlines Logo
6:20 pm - 10:45 amORD  Chicago O'Hare Intl-YWG Winnipeg
16h 25m1 stop Toronto Island
$366Porter Airlines
Sat, Nov 7 - Mon, Nov 23
Porter Airlines Logo
7:05 pm - 11:40 amYWG  Winnipeg-ORD Chicago O'Hare Intl
16h 35m1 stop Toronto Pearson Intl
Porter Airlines Logo
6:20 pm - 10:45 amORD  Chicago O'Hare Intl-YWG Winnipeg
16h 25m1 stop Toronto Island
$366Porter Airlines
Sat, Nov 7 - Fri, Nov 20
United Airlines Logo
2:15 pm - 4:50 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 35mnonstop
United Airlines Logo
9:35 am - 12:23 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 48mnonstop
$713United Airlines
Mon, Nov 23 - Wed, Dec 2
United Airlines Logo
2:15 pm - 4:50 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 35mnonstop
United Airlines Logo
8:44 am - 8:48 pmORD  Chicago O'Hare Intl-YWG Winnipeg
12h 04m1 stop Denver Intl
$713United Airlines
Mon, Nov 23 - Tue, Dec 1

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WestJet flights from Winnipeg to Chicago O'Hare Intl Airport

Our best WestJet deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
WestJet
Oct 8
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 11
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$443
WestJet
Oct 4
YWG10:10 amWinnipeg
30h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 8
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$465
WestJet
Oct 1
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
$513

Porter Airlines flights from Winnipeg to Chicago O'Hare Intl Airport

Our best Porter Airlines deals on Winnipeg to Chicago O'Hare Intl Airport flight tickets
Porter Airlines
Nov 7
YWG11:40 amWinnipeg
24h 00m
2 stops
ORD11:40 amChicago O'Hare Intl
Nov 21
ORD6:20 pmChicago O'Hare Intl
16h 25m
1 stop
YWG10:45 amWinnipeg
$362
Porter Airlines
Nov 7
YWG7:05 pmWinnipeg
16h 35m
1 stop
ORD11:40 amChicago O'Hare Intl
Nov 19
ORD12:20 pmChicago O'Hare Intl
9h 37m
1 stop
YWG9:57 pmWinnipeg
$365
Porter Airlines
Sep 17
YWG9:20 amWinnipeg
6h 58m
1 stop
ORD4:18 pmChicago O'Hare Intl
Sep 22
ORD11:42 amChicago O'Hare Intl
8h 07m
1 stop
YWG7:49 pmWinnipeg
$489

momondo Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Chicago O'Hare Intl Airport that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 11/7

11:40 am-11:40 am

2 stops24h 00m

Chicago O'Hare Intl

Thu 11/19

12:20 pm-9:57 pm

1 stop9h 37m

$361

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 11/7

11:40 am-11:40 am

2 stops24h 00m

Chicago O'Hare Intl

Sun 11/22

12:20 pm-12:44 am

1 stop12h 24m

$361

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 11/7

11:40 am-11:40 am

2 stops24h 00m

Chicago O'Hare Intl

Fri 11/20

12:20 pm-12:44 am

1 stop12h 24m

$361

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 11/7

11:40 am-11:40 am

2 stops24h 00m

Chicago O'Hare Intl

Mon 11/23

12:20 pm-9:57 pm

1 stop9h 37m

$362

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 11/7

11:40 am-11:40 am

2 stops24h 00m

Chicago O'Hare Intl

Sat 11/21

6:20 pm-10:45 am

1 stop16h 25m

$362

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 11/7

7:05 pm-11:40 am

1 stop16h 35m

Chicago O'Hare Intl

Thu 11/19

12:20 pm-9:57 pm

1 stop9h 37m

$365

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 11/7

7:05 pm-11:40 am

1 stop16h 35m

Chicago O'Hare Intl

Mon 11/23

6:20 pm-10:45 am

1 stop16h 25m

$366

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 11/7

7:05 pm-11:40 am

1 stop16h 35m

Chicago O'Hare Intl

Fri 11/20

6:20 pm-10:45 am

1 stop16h 25m

$366
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 11/23

2:15 pm-4:50 pm

Nonstop2h 35m

Chicago O'Hare Intl

Wed 12/2

9:35 am-12:23 pm

Nonstop2h 48m

$713

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Mon 11/23

2:15 pm-4:50 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 12/1

8:44 am-8:48 pm

1 stop12h 04m

$713

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 O'Hare Intl Airport

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 typical price of a round-trip flight between Winnipeg and Chicago O'Hare Intl Airport?

Prices are currently typical for flights on this route.

Typical prices usually range from $335 to $628.
The lowest price recently found on this route was $361.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Winnipeg averaging around $507.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $603. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $781.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Winnipeg at noon is the least expensive time of day to depart. momondo users have found prices as low as $642 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $663. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Winnipeg to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Winnipeg to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Winnipeg to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

You could potentially save up to 57% on your flight if you consider stops on a Winnipeg to Chicago O'Hare Intl Airport flight.

How have Winnipeg to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Winnipeg to Chicago O'Hare Intl Airport

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

Cheap Winnipeg to Chicago O'Hare Intl Airport (YWG to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago O'Hare Intl Airport

Best Price Found

$165

Fastest flight time

2h 35m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Winnipeg in the past 72 hours is $165. The best round-trip flight deal from Winnipeg to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $361.
The fastest flight from Winnipeg to Chicago O'Hare Intl Airport takes 2h 35m
Direct flights go from Winnipeg to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Winnipeg to Chicago O'Hare Intl Airport

  • How far is Winnipeg to Chicago O'Hare Intl by plane?

    There are 702.3 mi between Winnipeg and Chicago O'Hare Intl. A reasonable flight in good conditions will take 2h 35m.

  • When did momondo last update prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Winnipeg Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Winnipeg Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Winnipeg Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Winnipeg Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport. 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 Chicago O'Hare Intl Airport?

  • What is the most popular airline from Winnipeg to Chicago O'Hare Intl Airport?

Best airlines flying from Winnipeg to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Winnipeg to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $335Free CancellationRating
7.4
10,171 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago O'Hare Intl Airport

    United Airlines flies from Winnipeg to Chicago O'Hare Intl Airport around 9 times per week, with 10,171 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Winnipeg to Chicago O'Hare Intl Airport in the last 72 hours was $335 (round-trip), much lower than the average airfare cost of $701 for United Airlines flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
Skokie

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?

Flights from Winnipeg to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Winnipeg to Chicago 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 Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Winnipeg and alert you when they change.

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