Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Chicago from $144

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 3/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:55 pm - 4:43 pm
YWG
-
ORD
21h 48m
1 stop
WestJet Logo
5:30 pm - 2:30 pm
ORD
-
YWG
21h 00m
1 stop
$303WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m
1 stop
WestJet Logo
5:30 pm - 11:40 am
ORD
-
YWG
18h 10m
1 stop
$304WestJet
Tue, Jun 16 - Mon, Jun 22
Multiple Airlines Logo
7:30 am - 5:57 pm
YWG
-
ORD
10h 27m
1 stop
Multiple Airlines Logo
9:28 am - 12:40 am
ORD
-
YWG
15h 12m
2 stops
$309Multiple Airlines
Wed, Mar 11 - Wed, Mar 18
Multiple Airlines Logo
5:00 am - 8:09 pm
YWG
-
ORD
15h 09m
2 stops
Multiple Airlines Logo
7:41 pm - 3:09 pm
ORD
-
YWG
19h 28m
1 stop
$316Multiple Airlines
Sat, Mar 7 - Tue, Mar 10
WestJet Logo
9:00 pm - 4:43 pm
YWG
-
ORD
19h 43m
1 stop
WestJet Logo
5:30 pm - 10:00 am
ORD
-
YWG
16h 30m
1 stop
$319WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
6:55 pm - 4:43 pm
YWG
-
ORD
21h 48m
1 stop
WestJet Logo
5:30 pm - 8:48 pm
ORD
-
YWG
27h 18m
2 stops
$323WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m
1 stop
WestJet Logo
2:20 pm - 3:20 pm
ORD
-
YWG
25h 00m
1 stop
$328WestJet
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m
1 stop
Multiple Airlines Logo
5:32 pm - 7:25 pm
ORD
-
YWG
25h 53m
2 stops
$335Multiple Airlines
Fri, Apr 17 - Tue, Apr 21
WestJet Logo
5:00 pm - 4:43 pm
YWG
-
ORD
23h 43m
2 stops
WestJet Logo
5:30 pm - 8:48 pm
ORD
-
YWG
27h 18m
2 stops
$336WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m
1 stop
WestJet Logo
5:30 pm - 8:48 pm
ORD
-
YWG
27h 18m
2 stops
$337WestJet
Wed, Jun 17 - Mon, Jun 22

Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets
Porter Airlines
Mar 7
YWG6:00 amWinnipeg
6h 35m
1 stop
ORD12:35 pmChicago O'Hare Intl
Mar 10
ORD8:12 amChicago O'Hare Intl
7h 18m
1 stop
YWG3:30 pmWinnipeg
$465
Porter Airlines
Feb 26
YWG12:10 pmWinnipeg
7h 07m
1 stop
ORD7:17 pmChicago O'Hare Intl
Mar 1
ORD8:14 amChicago O'Hare Intl
7h 16m
1 stop
YWG3:30 pmWinnipeg
$495
Porter Airlines
Mar 11
YWG4:25 pmWinnipeg
17h 40m
2 stops
MDW10:05 amChicago Midway
Mar 18
MDW11:00 amChicago Midway
24h 13m
2 stops
YWG11:13 amWinnipeg
$705

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
Apr 25
YWG6:55 pmWinnipeg
21h 48m
1 stop
ORD4:43 pmChicago O'Hare Intl
Apr 30
ORD5:30 pmChicago O'Hare Intl
21h 00m
1 stop
YWG2:30 pmWinnipeg
$303
WestJet
Jun 16
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl
Jun 22
ORD5:30 pmChicago O'Hare Intl
18h 10m
1 stop
YWG11:40 amWinnipeg
$304
WestJet
Apr 25
YWG9:00 pmWinnipeg
19h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Apr 30
ORD5:30 pmChicago O'Hare Intl
16h 30m
1 stop
YWG10:00 amWinnipeg
$319

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chicago 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 January 25, 2026.
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

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/25

6:55 pm-4:43 pm

1 stop21h 48m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-2:30 pm

1 stop21h 00m

$303

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 6/16

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Mon 6/22

5:30 pm-11:40 am

1 stop18h 10m

$304

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 3/11

7:30 am-5:57 pm

1 stop10h 27m

Chicago O'Hare Intl

Wed 3/18

9:28 am-12:40 am

2 stops15h 12m

$309

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 3/7

5:00 am-8:09 pm

2 stops15h 09m

Chicago O'Hare Intl

Tue 3/10

7:41 pm-3:09 pm

1 stop19h 28m

$316

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/25

9:00 pm-4:43 pm

1 stop19h 43m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-10:00 am

1 stop16h 30m

$319

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/25

6:55 pm-4:43 pm

1 stop21h 48m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-8:48 pm

2 stops27h 18m

$323

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 3/9

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Mon 3/16

2:20 pm-3:20 pm

1 stop25h 00m

$328

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 4/17

6:15 am-1:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Tue 4/21

5:32 pm-7:25 pm

2 stops25h 53m

$335

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 4/25

5:00 pm-4:43 pm

2 stops23h 43m

Chicago O'Hare Intl

Thu 4/30

5:30 pm-8:48 pm

2 stops27h 18m

$336

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 6/17

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

Mon 6/22

5:30 pm-8:48 pm

2 stops27h 18m

$337

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 September is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $354. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Winnipeg to Chicago during October average around $358.

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 Thursday when prices can be found for as low as $523. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $799.

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 $606. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $623.

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 68% 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 January 2026, prices for Winnipeg to Chicago flights are approximately 52% 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

$243

Fastest flight time

2h 21m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $243. 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 3 airports in Chicago. From Winnipeg there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • 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
United AirlinesPriceFrom $199Free CancellationRating
7.4
9,198 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $199 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $469 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 2/24
Tue 3/3
By creating a price alert you accept our terms of use and privacy policy.

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