ORD - YWG

$196 Find Cheap Flights from Chicago O'Hare Airport to Winnipeg - Compare and Save

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Everything you should know

Cheapest round-trip
$440
Typical prices: $687-$1,047
Multiple Airlines
Tue 12/4Thu 12/6
ORD - YWG • 1 stop
Cheapest non-stop
$916
Typical prices: $762-$1,149
Air Canada
Mon 12/3Thu 12/6
ORD - YWG • Non-stop
Nonstop flights
You can fly direct with United Airlines. Average duration is 2h 47m
Direct flights
+1
Direct flights
+1
When to travel
Cheapest • 68% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $445 (round-trip)
Shortest trip • 4h 37m (one-way)
Insights
Insights
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Expert advice
Flight Deals

Cheap Flights from O'Hare Intl to Winnipeg (ORD-YWG)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Winnipeg

Fri, Dec 4 - Sun, Dec 6
Multiple Airlines Logo
10:05 am - 7:10 pmORD  Chicago O'Hare Intl-YWG Winnipeg
8h 05m1 stop Toronto Pearson Intl
Multiple Airlines Logo
11:00 am - 7:58 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 58m1 stop Toronto Pearson Intl
$440Multiple Airlines
Mon, Dec 21 - Thu, Jan 28
Multiple Airlines Logo
5:58 am - 2:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
7h 42m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:35 pm - 11:50 amYWG  Winnipeg-ORD Chicago O'Hare Intl
15h 15m2 stops Calgary Atlanta Hartsfield-Jackson
$464Multiple Airlines
Fri, Feb 5 - Tue, Feb 9
Multiple Airlines Logo
6:00 am - 2:40 pmORD  Chicago O'Hare Intl-YWG Winnipeg
7h 40m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
11:40 am - 11:30 amYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 50m2 stops Ottawa Toronto Island
$469Multiple Airlines
Wed, Nov 11 - Thu, Nov 19
Air Canada Logo
4:30 pm - 12:44 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 14m1 stop Toronto Pearson Intl
Air Canada Logo
9:15 am - 7:58 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
11h 43m1 stop Toronto Pearson Intl
$649Air Canada
Thu, Dec 10 - Thu, Dec 17
Air Canada Logo
7:02 am - 3:09 pmORD  Chicago O'Hare Intl-YWG Winnipeg
7h 07m1 stop Toronto Pearson Intl
Air Canada Logo
6:15 am - 1:13 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
7h 58m1 stop Toronto Pearson Intl
$703Air Canada
Fri, Apr 2 - Tue, Apr 6
Air Canada Logo
7:10 am - 1:48 pmORD  Chicago O'Hare Intl-YWG Winnipeg
6h 38m1 stop Toronto Pearson Intl
Air Canada Logo
5:15 am - 12:55 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
7h 40m1 stop Toronto Pearson Intl
$730Air Canada
Tue, Mar 16 - Sat, Mar 20
United Airlines Logo
3:50 pm - 6:41 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 51mnonstop
United Airlines Logo
7:00 am - 9:31 amYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 31mnonstop
$1,016United Airlines
Sat, Mar 13 - Sat, Mar 20
United Airlines Logo
3:50 pm - 7:41 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 51mnonstop
United Airlines Logo
7:00 am - 9:31 amYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 31mnonstop
$1,016United Airlines
Sun, Mar 14 - Fri, Mar 19
United Airlines Logo
3:50 pm - 6:41 pmORD  Chicago O'Hare Intl-YWG Winnipeg
2h 51mnonstop
United Airlines Logo
7:00 am - 9:31 amYWG  Winnipeg-ORD Chicago O'Hare Intl
2h 31mnonstop
$1,016United Airlines
Fri, Nov 20 - Tue, Nov 24
WestJet Logo
2:03 pm - 5:25 pmORD  Chicago O'Hare Intl-YWG Winnipeg
26h 22m2 stops Salt Lake City Calgary
WestJet Logo
9:05 pm - 8:17 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
24h 12m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
$1,072WestJet
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to Winnipeg flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What's the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Winnipeg?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Winnipeg. It’s 34% cheaper than the average day, while Monday is the most expensive, with prices 34% higher.

What’s the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg?

•September is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg at $255 round-trip.
•February ($1,543) and October ($1,079) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 505% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Expert advice

Expert advice for your flight from O'Hare Intl to Winnipeg

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and Air Canada

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.

Key details for Chicago O'Hare Intl Airport to Winnipeg flights

Low season

February

Cheapest flight

$196
Beat the crowds with an average 62% drop in travelers.
The most popular month to fly with an average 64% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Winnipeg

When to book flights from O'Hare Intl to Winnipeg

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago O'Hare Intl Airport to Winnipeg flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago O'Hare Intl Airport to Winnipeg?

    These are the earliest and latest flight times available from Chicago O'Hare Intl Airport to Winnipeg:

    • Earliest: departs at 9:29 am and lands at 12:16 pm
    • Latest: departs at 3:50 pm and lands at 6:37 pm.

    The flight takes about 2h 47m.

  • What cabin classes can I book on flights from Chicago O'Hare Intl Airport to Winnipeg?

    Only Economy Class is available on flights from Chicago O'Hare Intl Airport to Winnipeg.

  • How long is a flight from Chicago O'Hare Intl Airport to Winnipeg?

    A nonstop flight from Chicago O'Hare Intl Airport to Winnipeg takes 2h 47m, covering 706 miles.

  • Do I need a passport to fly from Chicago O'Hare Intl Airport to Winnipeg?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago O'Hare Intl Airport to Winnipeg flight?

    Round-trip flights from Chicago O'Hare Intl Airport to Winnipeg range from $687 to $1,047, with an average of $789 over the past 12 months. Anything below $687 counts as a good deal.

  • How much can I save by taking a layover when flying from Chicago O'Hare Intl Airport to Winnipeg?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $445 round-trip via Calgary (YYC), compared to $877 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago O'Hare Intl Airport to Winnipeg?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$86 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago O'Hare Intl Airport to Winnipeg?

    The Embraer 175 (Enhanced Winglets) family is used most often on this route, operated mainly by Air Canada and United Airlines. Other aircraft seen on the route include Boeing 777-300 variants.

  • How are flight departures from Chicago O'Hare Intl Airport to Winnipeg spread across the day?

    Morning is the busiest departure period on Chicago O'Hare Intl Airport to Winnipeg flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Chicago O'Hare Intl Airport to Winnipeg changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $440 to $1,611. That means the highest observed fare was about 4x higher than the lowest one.

  • How are flight prices from Chicago O'Hare Intl Airport to Winnipeg looking right now?

    One-way fares from Chicago O'Hare Intl Airport to Winnipeg are currently higher than usual. Average one-way flight prices are about $374, which is 11% above the typical average for this route.

  • What car rental options are available at Winnipeg Airport (YWG)?

    Winnipeg Airport (YWG) hosts 5 major car rental companies, with daily rates averaging $44 for economy cars. Top options include:

    • Thrifty
    • Dollar
    • Hertz
    • Alamo
    • Fox

  • Which airports can I use when flying from Chicago O'Hare Intl Airport to Winnipeg?

    Flights from Chicago O'Hare Intl Airport to Winnipeg usually depart from Chicago O'Hare Intl (ORD) and arrive at Winnipeg (YWG).

  • Which airports do connecting flights from Chicago O'Hare Intl Airport to Winnipeg pass through?

    One-stop flights from Chicago O'Hare Intl Airport to Winnipeg most commonly connect through:

    • Toronto Pearson Intl (YYZ) - 46% of one-stop connections
    • Minneapolis St Paul (MSP) - 36% of one-stop connections
    • Calgary (YYC) - 18% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago O'Hare Intl Airport to Winnipeg?

    Yes. Flexible dates can save you up to 51% on flights from Chicago O'Hare Intl Airport to Winnipeg. Wednesday is the cheapest departure day at $528 round-trip on average, while Monday is the most expensive at $1,062, a difference of $534.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago O'Hare Intl Airport to Winnipeg?

    Only United Airlines operates flights between Chicago O'Hare Intl Airport and Winnipeg.

  • How much time can I save by choosing a different layover airport from Chicago O'Hare Intl Airport to Winnipeg?

    Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 4h 37m, compared with 6h 50m via Toronto Pearson Intl (YYZ) and 9h 32m via Calgary (YYC).

  • Which airlines offer extra legroom and free seat selection on Chicago O'Hare Intl Airport to Winnipeg flights?

    Among airlines operating Chicago O'Hare Intl Airport to Winnipeg flights:

    • Air Canada: offers free seat selection
    • United Airlines: offers extra legroom; offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago O'Hare Intl Airport to Winnipeg flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Air Canada: a cabin bag and a checked bag in Economy Class
    • United Airlines: a cabin bag and a checked bag in Economy Class
    • Air New Zealand: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago O'Hare Intl Airport to Winnipeg flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Monday. On this route, Wednesday flights average $528, about $534 less than Monday fares (50% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago O'Hare Intl Airport to Winnipeg trip for September. Fares historically average $255 round-trip in that month - typically $1,288 less than the most expensive month, which is February (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Calgary Airport (YYC) can be cheaper than flying direct. The cheapest layover option averages $445 round-trip on this route - about $431 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Winnipeg Airport.

    • Victoria Inn Hotel & Convention Centre
    • Lakeview Signature, Trademark Collection by Wyndham
    • The Grand Winnipeg Airport Hotel by Lakeview

Prefer to fly direct from Chicago O'Hare Airport to Winnipeg?

 
Find which airlines fly direct from Chicago O'Hare Intl Airport to Winnipeg Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl 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 O'Hare Intl

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

More options for your flight from O'Hare Intl to Winnipeg

Complete your trip to Winnipeg with a hotel stay or car rental