CHI - YWG

$140 Find Cheap Flights from Chicago to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Winnipeg departing on 4/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Winnipeg, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$286
WestJet
Sun 4/26Sat 5/2
ORD - YWG • 1 stop
Cheapest non-stop
$736
Typical prices: $257-$584
United Airlines
Mon 5/11Mon 6/1
ORD - YWG • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers six inches more legroom.
Air Canada provides priority check-in for elite travelers.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $305 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 2h 42m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $356 (round-trip)
Shortest trip • 5h 53m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 52% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Winnipeg!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to Winnipeg (CHI-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Winnipeg

Sun, Apr 26 - Sat, May 2
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
6:00 am - 10:39 pm
YWG
-
ORD
16h 39m
2 stops
$286Multiple Airlines
Sun, Apr 26 - Sat, May 2
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
9:05 pm - 4:40 pm
YWG
-
ORD
19h 35m
1 stop
$305WestJet
Mon, Apr 27 - Sat, May 2
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
9:05 pm - 4:40 pm
YWG
-
ORD
19h 35m
1 stop
$311WestJet
Mon, Apr 27 - Sat, May 2
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
6:00 am - 10:39 pm
YWG
-
ORD
16h 39m
2 stops
$312Multiple Airlines
Mon, Apr 27 - Sat, May 2
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
9:05 pm - 4:40 pm
YWG
-
ORD
19h 35m
1 stop
$330WestJet
Sun, Apr 26 - Sat, May 2
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
WestJet Logo
9:05 pm - 4:40 pm
YWG
-
ORD
19h 35m
1 stop
$341WestJet
Sun, Apr 26 - Sat, May 2
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
Multiple Airlines Logo
2:55 pm - 10:23 am
YWG
-
ORD
19h 28m
3 stops
$348Multiple Airlines
Fri, Apr 24 - Tue, Apr 28
Multiple Airlines Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m
1 stop
Multiple Airlines Logo
9:05 pm - 10:02 am
YWG
-
ORD
12h 57m
2 stops
$352Multiple Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
4:28 pm - 3:09 pm
ORD
-
YWG
22h 41m
1 stop
Multiple Airlines Logo
9:05 pm - 10:02 am
YWG
-
ORD
12h 57m
2 stops
$360Multiple Airlines
Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
11:28 am - 3:09 pm
ORD
-
YWG
27h 41m
1 stop
Multiple Airlines Logo
9:05 pm - 5:00 pm
YWG
-
ORD
19h 55m
2 stops
$362Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Winnipeg flights

Get data-powered insights and trends into flights from Chicago to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Winnipeg flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Winnipeg costs $877 on the route between Chicago O'Hare Intl Airport (ORD) and Winnipeg (YWG). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Winnipeg?

The average price of all round-trip flights from Chicago to Winnipeg clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Winnipeg, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Winnipeg, Thursday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Chicago to Winnipeg?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Winnipeg, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Winnipeg is May, where tickets cost $284 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is $1,231 and $724 respectively.

Can I save money by flying with a layover from Chicago to Winnipeg?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $723 on average.

Expert advice

Expert advice for your flight from Chicago to Winnipeg

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada and United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Good to know

Low seasonSeptember
Cheapest flight$140
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago Midway Airport to Winnipeg

When to book flights from Chicago to Winnipeg

Are your dates flexible? Find out the best times to travel from Chicago to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Winnipeg

  • What is the cheapest flight from Chicago to Winnipeg?

    In the last 3 days, the lowest price for a flight from Chicago to Winnipeg was $140 for a one-way ticket and $286 for a round-trip.

  • Do I need a passport to fly between Chicago and Winnipeg?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Winnipeg.

  • Which airports will I be using when flying from Chicago to Winnipeg?

    On your way to Winnipeg, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Winnipeg.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Winnipeg?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Winnipeg flight route.

  • Which aircraft models fly most regularly from Chicago to Winnipeg?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago to Winnipeg flight route.

  • Which airline alliances offer flights from Chicago to Winnipeg?

    Star Alliance is the only airline alliance operating flights between Chicago and Winnipeg.

  • On which days can I fly direct from Chicago to Winnipeg?

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

  • How does KAYAK find such low prices on flights from Chicago to Winnipeg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Winnipeg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Winnipeg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Chicago to Winnipeg?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Winnipeg.
Find which airlines fly direct from Chicago to Winnipeg Airport, which days they fly and book direct flights.

Direct departures

Chicago to Winnipeg

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Winnipeg to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top airline flying from Chicago to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Winnipeg. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Winnipeg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9427 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
8.1Crew
6.6Food
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Everything you need to know for your flight from Chicago to Winnipeg

Information on your arrival and departure airports