Find Cheap Flights from Winnipeg to Chicago (YWG - CHI)

Flights overview

Useful information for finding cheap flights from Winnipeg to Chicago and booking your next trip

Cheapest round-trip flights	$378	WestJet 1 stop 22 hr Thu, Jun 11 — Mon, Jun 15	The cheapest round-trip flight from Winnipeg to Chicago is currently $378
Cheapest one-way flight	$193	WestJet 1 stop 10 hr Mon, Jun 1	The cheapest one-way flight from Winnipeg to Chicago is currently $193
Cheapest nonstop flights	$665	United Nonstop 3 hr Thu, Jun 18 — Sun, Jun 21	The cheapest nonstop round-trip flight from Winnipeg to Chicago is currently $665
Last-minute weekend getaway	$972	Delta, WestJet 2 stops 11 hr Thu, May 7 — Mon, May 11	The cheapest last-minute weekend getaway from Winnipeg to Chicago is currently $972
Cheapest business class flights	$891	United Nonstop 3 hr Thu, Jun 18 — Sun, Jun 21	The cheapest business class round-trip flight from Winnipeg to Chicago is currently $891

Fastest flight	2 hr 34 min	The fastest nonstop flight from Winnipeg to Chicago takes 2 hr 34 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Winnipeg to Chicago is typically October. The most expensive month to fly is typically March.

October Cheapest	Typical prices: $260–640
March Most expensive	Typical prices: $465–860

Popular airlines from Winnipeg to Chicago

United

Nonstop

from $665

Typical price: $455–800

7 weekly nonstop flights

YWG - ORD Every day

46 weekly connecting flights

YWG - ORD Every day
Delta

from $671

Typical price: $500–840

395 weekly connecting flights

YWG - MDW, ORD Every day
Air Canada

from $654

Typical price: $460–790

97 weekly connecting flights

YWG - ORD Every day
Porter Airlines

25 weekly connecting flights

YWG - MDW Every day
WestJet

from $378

Typical price: $420–770

16 weekly connecting flights

YWG - ORD Every Mon, Wed, Thu, Fri, Sat, Sun

Popular airports near Winnipeg

Winnipeg Richardson International Airport (YWG)

Winnipeg Canada 22 min 4 mi
Brandon Municipal Airport (YBR)

Brandon Canada 2 hr 20 min 125 mi
Kenora Airport (YQK)

Kenora Canada 2 hr 25 min 124 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Winnipeg to Chicago

The cheapest flights from Winnipeg to Chicago are usually in October. Typical ticket prices in October range from $260 to $640.

The cheapest round-trip flight from Winnipeg to Chicago recently found on Google Flights was with WestJet from $378. The cheapest one-way flight was with WestJet from $193.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest United flight from Winnipeg to Chicago is $665, flying from Jun 18 to Jun 21.
The cheapest Delta flight from Winnipeg to Chicago is $671, flying from Jul 23 to Jul 26.
The cheapest Air Canada flight from Winnipeg to Chicago is $654, flying from Jul 25 to Jul 26.
The cheapest WestJet flight from Winnipeg to Chicago is $378, flying from Jun 11 to Jun 15.

The cheapest round-trip flight from Winnipeg to Chicago starts at $378 from Thu, Jun 11 to Mon, Jun 15. The cheapest one-way flight starts at $193 and departs on Mon, Jun 1.

2 hr 34 min is the shortest flight time from Winnipeg to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Winnipeg to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Winnipeg to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Winnipeg to Chicago.

In terms of nonstop flights, United is the most popular. United offers 7 nonstop flights and 46 connecting flights per week. United flies from Winnipeg Richardson International Airport (YWG) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Delta is the most popular. Delta offers 395 connecting flights per week. Delta flies from Winnipeg Richardson International Airport (YWG) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Winnipeg to Chicago are:

Air Canada offers 97 connecting flights per week. Air Canada flies from Winnipeg Richardson International Airport (YWG) to Chicago O'Hare International Airport (ORD) .
Porter Airlines offers 25 connecting flights per week. Porter Airlines flies from Winnipeg Richardson International Airport (YWG) to Chicago Midway International Airport (MDW) .
WestJet offers 16 connecting flights per week. WestJet flies from Winnipeg Richardson International Airport (YWG) to Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between Winnipeg and Chicago.

The cheapest round-trip flight from Winnipeg to Chicago recently found on Google Flights was with WestJet from $378. The cheapest one-way flight was with WestJet from $193.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest United flight from Winnipeg to Chicago is $665, flying from Jun 18 to Jun 21.
The cheapest Delta flight from Winnipeg to Chicago is $671, flying from Jul 23 to Jul 26.
The cheapest Air Canada flight from Winnipeg to Chicago is $654, flying from Jul 25 to Jul 26.
The cheapest WestJet flight from Winnipeg to Chicago is $378, flying from Jun 11 to Jun 15.

United flies direct from Winnipeg to Chicago.

There are 7 United direct flights from Winnipeg to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Winnipeg and Chicago at price $972 is offered by Delta, WestJet from Thu, May 7 to Mon, May 11.

United flies direct from Winnipeg to Chicago.

There are 7 United direct flights from Winnipeg to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are direct flights from Winnipeg to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Winnipeg and Chicago start at $665 from Thu, Jun 18 to Sun, Jun 21 with United.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Winnipeg to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Winnipeg and Chicago start at $891 from Thu, Jun 18 to Sun, Jun 21 with United.

The cheapest economy class round-trip flights between Winnipeg and Chicago start at $378 from Thu, Jun 11 to Mon, Jun 15.

To book business class trips from Winnipeg to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Winnipeg and Chicago starts at $972 from Thu, May 7 to Mon, May 11 with Delta, WestJet.

The cheapest last-minute deal between Winnipeg and Chicago at price $972 is offered by Delta, WestJet from Thu, May 7 to Mon, May 11.

To find last-minute flight deals from Winnipeg to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.