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Cheap flights from Winnipeg to Chicago from $191

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
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
Multiple Airlines Logo
7:15 am - 5:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
34h 10m2 stops Atlanta Hartsfield-Jackson Calgary
$377Multiple Airlines
Thu, Oct 22 - Tue, Oct 27
Multiple Airlines Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
Multiple Airlines Logo
7:44 pm - 5:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
21h 41m2 stops Atlanta Hartsfield-Jackson Calgary
$379Multiple Airlines
Fri, Oct 23 - Mon, Oct 26
Multiple Airlines Logo
8:35 pm - 6:45 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
22h 10m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:26 pm - 4:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
22h 59m2 stops Atlanta Hartsfield-Jackson Calgary
$400Multiple Airlines
Wed, Nov 18 - Sat, Nov 21
Multiple Airlines Logo
8:35 pm - 7:59 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
23h 24m3 stops Calgary Atlanta Hartsfield-Jackson Houston George Bush Intcntl
Multiple Airlines Logo
5:26 pm - 4:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
22h 59m2 stops Atlanta Hartsfield-Jackson Calgary
$432Multiple Airlines
Wed, Nov 18 - Sat, Nov 21
Multiple Airlines Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
Multiple Airlines Logo
2:11 pm - 5:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
27h 14m3 stops Houston George Bush Intcntl Atlanta Hartsfield-Jackson Calgary
$440Multiple Airlines
Thu, Oct 22 - Tue, Oct 27
Multiple Airlines Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
Multiple Airlines Logo
3:30 pm - 5:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
25h 55m3 stops Las Vegas Harry Reid Intl Atlanta Hartsfield-Jackson Calgary
$447Multiple Airlines
Fri, Oct 23 - Mon, Oct 26
Multiple Airlines Logo
6:00 am - 6:43 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
12h 43m3 stops Calgary Regina Minneapolis St Paul
Multiple Airlines Logo
7:50 pm - 5:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
21h 35m2 stops Atlanta Hartsfield-Jackson Calgary
$456Multiple Airlines
Thu, Oct 22 - Tue, Oct 27
Multiple Airlines Logo
7:00 am - 7:05 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 05m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:10 am - 2:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
30h 30m1 stop Atlanta Hartsfield-Jackson
$457Multiple Airlines
Fri, Dec 18 - Tue, Dec 22
United Airlines Logo
6:55 pm - 7:00 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 05m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
United Airlines Logo
6:08 pm - 2:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 01m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$671United Airlines
Thu, Dec 3 - Mon, Dec 7
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
$676United Airlines
Wed, Nov 18 - Sun, Nov 22

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Porter Airlines flights from Winnipeg to Chicago

Our best Porter Airlines deals on Winnipeg to Chicago flight tickets
Porter Airlines
Oct 22
YWG9:20 amWinnipeg
6h 54m
1 stop
ORD4:14 pmChicago O'Hare Intl
Oct 29
ORD2:50 pmChicago O'Hare Intl
7h 07m
1 stop
YWG9:57 pmWinnipeg
$539
Porter Airlines
Nov 27
YWG7:00 amWinnipeg
7h 36m
1 stop
ORD2:36 pmChicago O'Hare Intl
Dec 1
ORD2:50 pmChicago O'Hare Intl
7h 07m
1 stop
YWG9:57 pmWinnipeg
$540
Porter Airlines
Oct 13
YWG11:40 amWinnipeg
7h 50m
2 stops
ORD7:30 pmChicago O'Hare Intl
Oct 18
ORD8:06 amChicago O'Hare Intl
7h 14m
1 stop
YWG3:20 pmWinnipeg
$541

Delta flights from Winnipeg to Chicago

Our best Delta deals on Winnipeg to Chicago flight tickets
Delta
Oct 1
YWG6:40 amWinnipeg
9h 57m
2 stops
ORD4:37 pmChicago O'Hare Intl
Oct 4
ORD8:25 amChicago O'Hare Intl
8h 29m
1 stop
YWG4:54 pmWinnipeg
$929
Delta
Oct 1
YWG6:40 amWinnipeg
6h 19m
2 stops
ORD12:59 pmChicago O'Hare Intl
Oct 4
ORD8:25 amChicago O'Hare Intl
6h 43m
1 stop
YWG3:08 pmWinnipeg
$941

momondo Fare Finder

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

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Route

Depart

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Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/22

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 10/27

7:15 am-5:25 pm

2 stops34h 10m

$377

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 10/23

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/26

7:44 pm-5:25 pm

2 stops21h 41m

$379

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 11/18

8:35 pm-6:45 pm

2 stops22h 10m

Chicago O'Hare Intl

Sat 11/21

5:26 pm-4:25 pm

2 stops22h 59m

$400

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 11/18

8:35 pm-7:59 pm

3 stops23h 24m

Chicago O'Hare Intl

Sat 11/21

5:26 pm-4:25 pm

2 stops22h 59m

$432

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/22

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 10/27

2:11 pm-5:25 pm

3 stops27h 14m

$440

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 10/23

7:00 am-4:40 pm

1 stop9h 40m

Chicago O'Hare Intl

Mon 10/26

3:30 pm-5:25 pm

3 stops25h 55m

$447

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/22

6:00 am-6:43 pm

3 stops12h 43m

Chicago O'Hare Intl

Tue 10/27

7:50 pm-5:25 pm

2 stops21h 35m

$456

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 12/18

7:00 am-7:05 am

1 stop24h 05m

Chicago O'Hare Intl

Tue 12/22

8:10 am-2:40 pm

1 stop30h 30m

$457

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 12/3

6:55 pm-7:00 pm

2 stops24h 05m

Chicago O'Hare Intl

Mon 12/7

6:08 pm-2:09 pm

2 stops20h 01m

$671
Quickest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Wed 11/18

2:15 pm-4:50 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sun 11/22

9:35 am-12:23 pm

Nonstop2h 48m

$676

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

Prices are currently low for flights on this route.

Typical prices usually range from $474 to $648.
The lowest price recently found on this route was $377.

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $491. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Winnipeg to Chicago during February average around $523.

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 $602. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $786.

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 $668. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $682.

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 58% 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 September 2026, prices for Winnipeg to Chicago flights are approximately 9% 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

$191

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 $191. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $377.
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?

  • 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 $471Free CancellationRating
7.4
10,246 reviews
Search United Airlines flights

  • United Airlines Flights From Winnipeg to Chicago

    United Airlines flight deals from Winnipeg to Chicago start from $471 round-trip. Over the 12 United Airlines flights for this route in a normal week, average airfare is usually $701 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
Portage
Benton Harbor
Saint Joseph
Lansing
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