Latest deals
Insights
FAQs
Reviews

Cheap flights from Winnipeg to Chicago from C$ 228

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 23/5. 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
From?
To?
Mon 20/5
Mon 27/5

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Early arrival? 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? Create a price alert to track prices.

Easily compare round-trip flights from Winnipeg to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Winnipeg to Chicago by changing tabs
Delta
11 Jun.
YWG6:55 a.m.Winnipeg
10h 09m
2 stops
MDW5:04 p.m.Chicago Midway
18 Jun.
MDW2:24 p.m.Chicago Midway
9h 05m
1 stop
YWG11:29 p.m.Winnipeg
WestJet
3 Jun.
YWG6:55 a.m.Winnipeg
11h 12m
1 stop
MDW6:07 p.m.Chicago Midway
11 Jun.
MDW9:29 a.m.Chicago Midway
14h 00m
1 stop
YWG11:29 p.m.Winnipeg
Multiple Airlines
18 Jul.
YWG8:00 a.m.Winnipeg
12h 49m
1 stop
MDW8:49 p.m.Chicago Midway
23 Jul.
MDW9:44 p.m.Chicago Midway
17h 38m
1 stop
YWG3:22 p.m.Winnipeg
Air Canada
11 Jun.
YWG2:18 p.m.Winnipeg
2h 28m
ORD4:46 p.m.Chicago O'Hare Intl
18 Jun.
ORD9:15 p.m.Chicago O'Hare Intl
11h 37m
1 stop
YWG8:52 a.m.Winnipeg
Porter Airlines
5 Jun.
YWG11:50 a.m.Winnipeg
9h 47m
2 stops
MDW9:37 p.m.Chicago Midway
8 Jun.
MDW8:00 a.m.Chicago Midway
10h 07m
2 stops
YWG6:07 p.m.Winnipeg
United Airlines
15 Jun.
YWG2:18 p.m.Winnipeg
2h 28m
ORD4:46 p.m.Chicago O'Hare Intl
1 Jul.
ORD9:08 p.m.Chicago O'Hare Intl
16h 13m
1 stop
YWG1:21 p.m.Winnipeg

Find the cheapest one-way flights from Winnipeg to Chicago

If you're looking for one-way flights from Winnipeg to Chicago, view some of our deals below provided by Air Canada, Delta and United Airlines
Delta
23 May
YWG6:55 a.m.Winnipeg
7h 47m
1 stop
ORD2:42 p.m.Chicago O'Hare Intl
Multiple Airlines
5 Jul.
YWG8:00 a.m.Winnipeg
8h 47m
1 stop
ORD4:47 p.m.Chicago O'Hare Intl
WestJet
4 Jul.
YWG6:30 a.m.Winnipeg
12h 01m
2 stops
MDW6:31 p.m.Chicago Midway

Search last-minute flights to Chicago from Winnipeg

Find and compare round-trip flight prices for your last-minute flight from Winnipeg to Chicago
WestJet
25 May
YWG7:30 a.m.Winnipeg
27h 32m
2 stops
MDW11:02 a.m.Chicago Midway
29 May
MDW4:41 p.m.Chicago Midway
22h 44m
1 stop
YWG3:25 p.m.Winnipeg
Delta
25 May
YWG6:55 a.m.Winnipeg
9h 18m
2 stops
MDW4:13 p.m.Chicago Midway
29 May
MDW7:10 p.m.Chicago Midway
4h 13m
1 stop
YWG11:23 p.m.Winnipeg
Multiple Airlines
24 May
YWG8:30 a.m.Winnipeg
20h 50m
2 stops
ORD5:20 a.m.Chicago O'Hare Intl
26 May
ORD8:30 a.m.Chicago O'Hare Intl
11h 18m
2 stops
YWG7:48 p.m.Winnipeg
Air Canada
25 May
YWG7:30 a.m.Winnipeg
6h 32m
1 stop
ORD2:02 p.m.Chicago O'Hare Intl
29 May
ORD1:03 p.m.Chicago O'Hare Intl
2h 26m
YWG3:29 p.m.Winnipeg
WestJet
24 May
YWG7:30 a.m.Winnipeg
9h 36m
2 stops
MDW5:06 p.m.Chicago Midway
26 May
MDW11:01 a.m.Chicago Midway
28h 24m
1 stop
YWG3:25 p.m.Winnipeg
Multiple Airlines
24 May
YWG8:30 a.m.Winnipeg
20h 50m
2 stops
ORD5:20 a.m.Chicago O'Hare Intl
26 May
ORD8:30 a.m.Chicago O'Hare Intl
30h 55m
3 stops
YWG3:25 p.m.Winnipeg

WestJet flights from Winnipeg to Chicago

Our best WestJet deals on Winnipeg to Chicago flight tickets
WestJet
3 Jun.
YWG6:55 a.m.Winnipeg
11h 12m
1 stop
MDW6:07 p.m.Chicago Midway
11 Jun.
MDW9:29 a.m.Chicago Midway
14h 00m
1 stop
YWG11:29 p.m.Winnipeg
WestJet
3 Jun.
YWG6:30 a.m.Winnipeg
11h 37m
2 stops
MDW6:07 p.m.Chicago Midway
11 Jun.
MDW9:29 a.m.Chicago Midway
14h 00m
1 stop
YWG11:29 p.m.Winnipeg
WestJet
25 May
YWG7:30 a.m.Winnipeg
27h 32m
2 stops
MDW11:02 a.m.Chicago Midway
29 May
MDW4:41 p.m.Chicago Midway
22h 44m
1 stop
YWG3:25 p.m.Winnipeg

United Airlines flights from Winnipeg to Chicago

Our best United Airlines deals on Winnipeg to Chicago flight tickets
United Airlines
15 Jun.
YWG2:18 p.m.Winnipeg
2h 28m
ORD4:46 p.m.Chicago O'Hare Intl
1 Jul.
ORD9:08 p.m.Chicago O'Hare Intl
16h 13m
1 stop
YWG1:21 p.m.Winnipeg
United Airlines
13 Jun.
YWG2:18 p.m.Winnipeg
2h 28m
ORD4:46 p.m.Chicago O'Hare Intl
20 Jun.
ORD1:03 p.m.Chicago O'Hare Intl
2h 26m
YWG3:29 p.m.Winnipeg
United Airlines
11 Jun.
YWG2:18 p.m.Winnipeg
2h 28m
ORD4:46 p.m.Chicago O'Hare Intl
18 Jun.
ORD1:03 p.m.Chicago O'Hare Intl
2h 26m
YWG3:29 p.m.Winnipeg

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 from Winnipeg to Chicago?

November. The cheapest time of year to fly to Chicago from Winnipeg is November. The most expensive is August.

What is the cheapest day to depart Winnipeg for Chicago?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Winnipeg to Chicago?

In the evening. Winnipeg to Chicago flights are approximately 12% more expensive in the morning than in the evening

What is the cheapest airline that flies to Chicago from Winnipeg?

Air Canada. Air Canada, Delta, and Endeavor Airlines are the most popular carriers operating from Winnipeg to Chicago

What is the cheapest Winnipeg to Chicago flight route?

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

How far in advance should you book Winnipeg to Chicago flights?

16 days before. The cheapest time to buy a flight from Winnipeg to Chicago is approximately 16 days to departure

Can stopping save me money on Winnipeg to Chicago flights?

You could potentially save up to 49% on your flight if you consider stops on a Winnipeg to Chicago flight.

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

C$ 228

Fastest flight time

2h 28m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is C$ 228. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 384.
The fastest flight from Winnipeg to Chicago takes 2h 28m
Direct flights go from Winnipeg to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Winnipeg to Chicago by plane?

    A flight from Winnipeg to Chicago will travel around 1153.0 km. 2h 28m is a normal flight duration for this route.

  • 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 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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago 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. We always recommend checking with your airline or a trusted third party such as IATA to get advice.


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
Air CanadaPriceFrom C$ 390Free CancellationRating
7.0
6,944 reviews
Search Air Canada flights
Endeavor AirlinesPriceFrom C$ 462Free CancellationRating
8.8
4 reviews
Search Endeavor Airlines flights
DeltaPriceFrom C$ 478Free CancellationRating
8.0
10,691 reviews
Search Delta flights
United AirlinesPriceFrom C$ 605Free CancellationRating
7.4
10,946 reviews
Search United Airlines flights
WestJetPriceFrom C$ 656Free CancellationRating
7.5
2,920 reviews
Search WestJet flights
WestJet EncorePriceFrom C$ 784Free CancellationRating
8.1
46 reviews
Search WestJet Encore flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Chicago?

Finding the right flight to Chicago from Winnipeg is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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?

Once you have performed a search for Winnipeg to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 20/5
Mon 27/5
Email me momondo's favourite deals

Find better results for your stay in the United States

Fly into one of these airports located in Chicago
Airports listed have a maximum distance of 25.6 km from Chicago