Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Chicago from $178

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 5/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$310WestJet
Mon, May 25 - Fri, May 29
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$313WestJet
Sun, May 3 - Fri, May 8
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$321WestJet
Wed, May 27 - Fri, May 29
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$331WestJet
Tue, Sep 8 - Tue, Sep 22
Multiple Airlines Logo
9:05 pm - 7:55 am
YWG
-
ORD
34h 50m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$343Multiple Airlines
Wed, May 27 - Fri, May 29
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$346WestJet
Tue, Sep 8 - Mon, Sep 21
WestJet Logo
9:05 pm - 4:40 pm
YWG
-
ORD
19h 35m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$353WestJet
Tue, May 26 - Fri, May 29
Air Canada Logo
10:55 am - 8:05 pm
YWG
-
ORD
9h 10m
1 stop
Air Canada Logo
9:50 am - 4:17 pm
ORD
-
YWG
6h 27m
1 stop
$373Air Canada
Sat, Sep 5 - Sat, Sep 19
Delta Logo
12:46 pm - 6:18 pm
YWG
-
MDW
5h 32m
1 stop
Delta Logo
9:54 am - 3:19 pm
MDW
-
YWG
5h 25m
1 stop
$377Delta
Wed, Jun 10 - Sat, Jun 13
Multiple Airlines Logo
9:05 pm - 11:09 am
YWG
-
MDW
14h 04m
2 stops
Multiple Airlines Logo
3:20 pm - 9:45 am
MDW
-
YWG
18h 25m
1 stop
$384Multiple Airlines
Thu, May 28 - Mon, Jun 1

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
May 25
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 29
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$310
WestJet
May 3
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 8
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$313
WestJet
May 27
YWG7:00 amWinnipeg
9h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 29
ORD5:30 pmChicago O'Hare Intl
7h 25m
1 stop
YWG12:55 amWinnipeg
$321

Air Canada flights from Winnipeg to Chicago

Our best Air Canada deals on Winnipeg to Chicago flight tickets
Air Canada
Sep 5
YWG10:55 amWinnipeg
9h 10m
1 stop
ORD8:05 pmChicago O'Hare Intl
Sep 19
ORD9:50 amChicago O'Hare Intl
6h 27m
1 stop
YWG4:17 pmWinnipeg
$373
Air Canada
Sep 9
YWG5:10 amWinnipeg
9h 42m
2 stops
ORD2:52 pmChicago O'Hare Intl
Sep 23
ORD9:50 amChicago O'Hare Intl
6h 27m
1 stop
YWG4:17 pmWinnipeg
$386
Air Canada
Aug 25
YWG5:10 amWinnipeg
8h 12m
1 stop
ORD1:22 pmChicago O'Hare Intl
Aug 29
ORD2:15 pmChicago O'Hare Intl
7h 15m
1 stop
YWG9:30 pmWinnipeg
$398

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 April 14, 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

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 5/25

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 5/29

5:30 pm-12:55 am

1 stop7h 25m

$310

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 5/3

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 5/8

5:30 pm-12:55 am

1 stop7h 25m

$313

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 5/27

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 5/29

5:30 pm-12:55 am

1 stop7h 25m

$321

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 9/8

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 9/22

5:30 pm-12:55 am

1 stop7h 25m

$331

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 5/27

9:05 pm-7:55 am

2 stops34h 50m

Chicago O'Hare Intl

Fri 5/29

5:30 pm-12:55 am

1 stop7h 25m

$343

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 9/8

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 9/21

5:30 pm-12:55 am

1 stop7h 25m

$346

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 5/26

9:05 pm-4:40 pm

1 stop19h 35m

Chicago O'Hare Intl

Fri 5/29

5:30 pm-12:55 am

1 stop7h 25m

$353

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 9/5

10:55 am-8:05 pm

1 stop9h 10m

Chicago O'Hare Intl

Sat 9/19

9:50 am-4:17 pm

1 stop6h 27m

$373
Quickest round-trip

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Wed 6/10

12:46 pm-6:18 pm

1 stop5h 32m

Chicago Midway

Sat 6/13

9:54 am-3:19 pm

1 stop5h 25m

$377

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 5/28

9:05 pm-11:09 am

2 stops14h 04m

Chicago Midway

Mon 6/1

3:20 pm-9:45 am

1 stop18h 25m

$384

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 typical price of a round-trip flight between Winnipeg and Chicago?

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 $358. 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 $495. 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 $599. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $625.

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.

How have Winnipeg to Chicago flight prices changed over time?

As of April 2026, prices for Winnipeg to Chicago flights are approximately 15% cheaper 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

$218

Fastest flight time

2h 34m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is $218. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $465.
The fastest flight from Winnipeg to Chicago takes 2h 34m
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 34m.

  • 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
9,581 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 7 United Airlines flights for this route in a normal week, average airfare is usually $517 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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
Thu 5/14
Thu 5/21
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