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Cheap flights from Chicago (CHI) to Winnipeg (YWG) from $129

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/23. 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.
CHI — YWG
Apr 30 — May 71
From?
To?
Tue 4/30
Tue 5/7
1 adult, Economy
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The best prices from Chicago to Winnipeg are usually found in May or January, booked 8 days in advance, depart on a Thursday or Monday and return on a Wednesday

Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 25, 2024.

Popular in

December

Cheapest in

May

Round-trip from

$382

One-way from

$267
High demand for flights, 34% potential price rise
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Best time to find cheap flights, 35% potential price drop
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From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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What is the cheapest day to fly round-trip from Chicago to Winnipeg?

Saturday flights are generally found to be more expensive for flights from Chicago to Winnipeg. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Winnipeg.

How far in advance should I book a flight from Chicago to Winnipeg?

To save up to 162% on this flight, we recommend booking at least 8 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Winnipeg from $337 1-2 weeks out and tickets from $1,274 for flights departing within the next 72 hours.

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

May can be a great time to fly to Winnipeg from Chicago with a flight ticket averaging about $590. Cheapflights users have found deals in the month of May for as cheap as $207. The most expensive prices can be found in the month of December.

When is the cheapest time to fly from Chicago to Winnipeg (CHI - YWG)?

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 31% on airfare.

Cheap Air Canada flights from Chicago to Winnipeg

Explore cheap flight options specifically provided by Air Canada for the route between Chicago and Winnipeg. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Consider these cheap Air Canada flights we've found departing from Chicago to Winnipeg. Be sure to come back soon if the deals available don't appeal to you at this time.
Fri 6/219:15 pmORD - YWG
1 stop12h 32mAir Canada
Tue 6/257:30 amYWG - ORD
1 stop7h 24mAir Canada
Deal found 4/24$444
Tue 6/186:00 amORD - YWG
1 stop9h 57mAir Canada
Wed 6/197:30 amYWG - ORD
1 stop7h 24mAir Canada
Deal found 4/24$467
Sat 6/16:00 pmORD - YWG
1 stop6h 10mAir Canada
Sat 7/68:15 amYWG - ORD
1 stop6h 25mAir Canada
Deal found 4/24$501
Tue 5/289:15 pmORD - YWG
1 stop11h 40mAir Canada
Wed 7/35:10 amYWG - ORD
1 stop7h 49mAir Canada
Deal found 4/24$524
Tue 5/289:15 pmORD - YWG
1 stop11h 40mAir Canada
Sun 7/75:00 amYWG - ORD
1 stop7h 54mAir Canada
Deal found 4/24$530
Tue 6/189:15 pmORD - YWG
1 stop14h 07mAir Canada
Wed 6/192:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Deal found 4/23$556
Fri 5/246:00 amORD - YWG
1 stop10h 00mAir Canada
Sun 5/268:15 amYWG - ORD
1 stop6h 26mAir Canada
Deal found 4/24$567
Mon 5/271:03 pmORD - YWG
Nonstop2h 26mAir Canada
Wed 7/38:15 amYWG - ORD
1 stop6h 25mAir Canada
Deal found 4/24$619
Sun 5/56:00 amORD - YWG
1 stop10h 00mAir Canada
Thu 5/302:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Deal found 4/24$629

Cheap Delta flights from Chicago to Winnipeg

Explore cheap flight options specifically provided by Delta for the route between Chicago and Winnipeg. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Some of the best deals we've found on Delta flights traveling from Chicago to Winnipeg. Make sure to examine the flight information before completing your reservation.
Tue 6/113:55 pmORD - YWG
1 stop7h 34mDelta
Thu 6/136:55 amYWG - ORD
1 stop8h 04mDelta
Deal found 4/24$398
Tue 6/112:24 pmMDW - YWG
1 stop9h 05mDelta
Thu 6/136:55 amYWG - MDW
2 stops5h 48mDelta
Deal found 4/24$408
Tue 6/113:55 pmORD - YWG
1 stop7h 34mDelta
Thu 6/136:55 amYWG - ORD
2 stops9h 53mDelta
Deal found 4/24$415
Wed 5/293:50 pmORD - YWG
1 stop7h 33mDelta
Tue 7/26:55 amYWG - ORD
1 stop8h 04mDelta
Deal found 4/24$451
Wed 5/18:45 amORD - YWG
2 stops14h 40mDelta
Fri 5/35:35 pmYWG - ORD
1 stop4h 24mDelta
Deal found 4/24$458
Wed 5/298:45 amORD - YWG
2 stops14h 38mDelta
Fri 7/56:55 amYWG - ORD
1 stop3h 41mDelta
Deal found 4/24$460
Wed 5/298:45 amORD - YWG
2 stops14h 38mDelta
Thu 7/46:55 amYWG - ORD
2 stops14h 08mDelta
Deal found 4/24$465
Tue 6/112:24 pmMDW - YWG
1 stop9h 05mDelta
Thu 6/138:00 amYWG - MDW
1 stop6h 55mDelta
Deal found 4/24$470
Fri 7/197:06 pmMDW - YWG
1 stop4h 19mDelta
Wed 7/246:55 amYWG - MDW
2 stops5h 49mDelta
Deal found 4/25$498

Cheap Chicago to Winnipeg flights in April & May 2024

Find cheap flight options from Chicago to Winnipeg specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,068,701 searches. Prices were last updated on April 25, 2024.
Check out some of the best flight deals from Chicago to Winnipeg in 2024. Check back in a little while for more flight options.
Wed 5/297:53 amMDW - YWG
1 stop7h 32mMultiple Airlines
Thu 7/48:00 amYWG - MDW
1 stop12h 49mMultiple Airlines
Deal found 4/24$330
Wed 5/16:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Fri 5/38:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Deal found 4/24$358
Wed 5/16:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Wed 5/88:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Deal found 4/25$370
Tue 5/286:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Wed 7/36:30 amYWG - ORD
2 stops14h 36mMultiple Airlines
Deal found 4/24$374
Tue 5/2810:57 pmORD - YWG
3 stops20h 06mMultiple Airlines
Wed 7/36:30 amYWG - ORD
2 stops14h 36mMultiple Airlines
Deal found 4/24$377
Tue 5/286:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Fri 7/128:50 pmYWG - ORD
3 stops23h 49mMultiple Airlines
Deal found 4/25$387
Thu 5/3011:48 amORD - YWG
2 stops12h 09mMultiple Airlines
Wed 7/108:00 amYWG - ORD
1 stop8h 39mMultiple Airlines
Deal found 4/25$399
Tue 5/286:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Thu 7/116:50 amYWG - ORD
1 stop10h 07mMultiple Airlines
Deal found 4/25$404
Sun 5/268:30 amORD - YWG
2 stops11h 18mMultiple Airlines
Fri 7/58:00 amYWG - ORD
1 stop8h 31mMultiple Airlines
Deal found 4/25$405

Chicago to Winnipeg 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Winnipeg in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Check out some of the best flight deals from Chicago to Winnipeg in 2024. Check back in a little while for more flight options.
Wed 5/297:53 amMDW - YWG
1 stop7h 32mMultiple Airlines
Thu 7/48:00 amYWG - MDW
1 stop12h 49mMultiple Airlines
Deal found 4/24$330
Wed 5/16:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Fri 5/38:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Deal found 4/24$358
Wed 5/16:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Wed 5/88:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Deal found 4/25$370
Tue 5/286:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Wed 7/36:30 amYWG - ORD
2 stops14h 36mMultiple Airlines
Deal found 4/24$374
Tue 5/2810:57 pmORD - YWG
3 stops20h 06mMultiple Airlines
Wed 7/36:30 amYWG - ORD
2 stops14h 36mMultiple Airlines
Deal found 4/24$377
Tue 5/286:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Fri 7/128:50 pmYWG - ORD
3 stops23h 49mMultiple Airlines
Deal found 4/25$387
Tue 6/113:55 pmORD - YWG
1 stop7h 34mDelta
Thu 6/136:55 amYWG - ORD
1 stop8h 04mDelta
Deal found 4/24$398
Thu 5/3011:48 amORD - YWG
2 stops12h 09mMultiple Airlines
Wed 7/108:00 amYWG - ORD
1 stop8h 39mMultiple Airlines
Deal found 4/25$399
Tue 5/286:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Thu 7/116:50 amYWG - ORD
1 stop10h 07mMultiple Airlines
Deal found 4/25$404

Non-stop flights to Winnipeg from Chicago

Discover non-stop flight options from Chicago to Winnipeg. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
To help reduce your travel time, choose from one of these non-stop flights from Chicago to Winnipeg. Search for alternative flights from Chicago to Winnipeg by utilizing the search form above.
Wed 5/291:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Fri 7/52:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Deal found 4/24$625
Fri 5/241:03 pmORD - YWG
Nonstop2h 26mAir Canada
Sun 5/262:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Deal found 4/24$636
Wed 5/291:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Tue 7/92:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Deal found 4/24$657
Thu 5/231:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Thu 7/42:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Deal found 4/24$716
Fri 5/241:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Thu 7/42:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Deal found 4/24$765
Thu 5/231:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Tue 7/92:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Deal found 4/24$776
Fri 5/241:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Tue 7/92:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Deal found 4/24$805
Fri 6/211:03 pmORD - YWG
Nonstop2h 26mAir Canada
Tue 6/252:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Deal found 4/24$818
Fri 6/211:03 pmORD - YWG
Nonstop2h 26mAir Canada
Tue 6/252:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Deal found 4/24$819

Chicago to Winnipeg flights leaving soon

Find last-minute flight options from Chicago to Winnipeg for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Have a look at some of the flights available from Chicago to Winnipeg departing last-minute. Users should be sure to double check the price, date, and time of their last-minute flight.
Wed 5/16:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Fri 5/38:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Deal found 4/24$358
Wed 5/16:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Wed 5/88:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Deal found 4/25$370
Wed 5/16:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Wed 5/88:00 amYWG - ORD
2 stops11h 19mMultiple Airlines
Deal found 4/25$435
Wed 5/15:32 amORD - YWG
1 stop9h 53mMultiple Airlines
Sat 5/46:50 amYWG - ORD
2 stops14h 15mMultiple Airlines
Deal found 4/24$441
Tue 4/309:34 pmORD - YWG
1 stop18h 31mMultiple Airlines
Wed 5/17:00 pmYWG - ORD
2 stops24h 03mMultiple Airlines
Deal found 4/24$456
Wed 5/18:45 amORD - YWG
2 stops14h 40mDelta
Fri 5/35:35 pmYWG - ORD
1 stop4h 24mDelta
Deal found 4/24$458
Wed 5/15:32 amORD - YWG
1 stop9h 53mWestJet
Thu 5/29:30 amYWG - ORD
2 stops14h 22mWestJet
Deal found 4/24$460
Tue 4/305:57 pmORD - YWG
1 stop21h 28mWestJet
Thu 5/27:30 amYWG - ORD
2 stops16h 22mWestJet
Deal found 4/24$471
Tue 4/3012:45 pmMDW - YWG
1 stop26h 40mWestJet
Thu 5/27:30 amYWG - MDW
2 stops15h 20mWestJet
Deal found 4/24$471

One-way flights to Winnipeg from Chicago

Search for one-way flight options from Chicago to Winnipeg. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
Take a look at some of the one-way flights we've detected from Chicago to Winnipeg. Those seeking round-trip flights from Chicago to Winnipeg should utilize the search form at the the top of the page.
Tue 7/239:44 pmMDW - YWG
1 stop17h 38mMultiple Airlines
Deal found 4/23$129
Wed 6/1910:12 pmORD - YWG
1 stop18h 04mMultiple Airlines
Deal found 4/24$183
Sun 7/217:00 amORD - YWG
3 stops15h 12mMultiple Airlines
Deal found 4/23$195
Mon 7/227:27 amMDW - YWG
1 stop7h 55mMultiple Airlines
Deal found 4/23$198
Sun 4/286:20 amORD - YWG
1 stop5h 19mDelta
Deal found 4/25$202
Wed 6/195:00 amORD - YWG
2 stops17h 20mMultiple Airlines
Deal found 4/24$203
Tue 7/233:57 pmORD - YWG
1 stop7h 28mDelta
Deal found 4/23$219
Sun 5/268:30 amORD - YWG
2 stops11h 18mMultiple Airlines
Deal found 4/25$220
Sun 7/219:44 pmMDW - YWG
1 stop17h 38mMultiple Airlines
Deal found 4/23$222

Find flights from Chicago to Winnipeg within your budget

Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$330 - $692

Route

Depart

Return

Price

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/29

1 stop7h 32m

Winnipeg

Thu 7/4

1 stop12h 49m

$330

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 5/1

1 stop9h 25m

Winnipeg

Fri 5/3

1 stop9h 27m

$358

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 5/1

1 stop9h 25m

Winnipeg

Wed 5/8

1 stop9h 27m

$370

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 6/11

1 stop7h 34m

Winnipeg

Thu 6/13

1 stop8h 04m

$398

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 6/11

1 stop9h 05m

Winnipeg

Thu 6/13

2 stops5h 48m

$408

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 6/4

2 stops16h 33m

Winnipeg

Sat 6/8

1 stop20h 15m

$417

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/21

1 stop12h 32m

Winnipeg

Tue 6/25

1 stop7h 24m

$444

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 4/29

1 stop9h 53m

Winnipeg

Wed 5/1

1 stop14h 58m

$448

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 5/26

2 stops9h 07m

Winnipeg

Tue 7/9

2 stops9h 32m

$692

Flights are sorted by cheapest first

Deals found on 4/24

When is the best time to book a flight from Chicago to Winnipeg?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Winnipeg. Price data was last updated on January 28, 2024.
The price you pay for your flight from Chicago to Winnipeg may vary depending on when you book. For the best chance of a lower fare, look to book 7 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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When is the cheapest time to fly from Chicago to Winnipeg?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Winnipeg. Price data was last updated on April 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Winnipeg flight should consider departing on Thursday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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Average price of flights to Winnipeg by month

Plan your trip from Chicago to Winnipeg by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Winnipeg is currently $197 while a round-trip flight costs $429. Price data was last updated on April 21, 2024.

Currently, November is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $382). Flying from Chicago to Winnipeg in July is currently the most expensive (average of $573). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$495

February

$514

March

$426

April

$506

May

$527

June

$552

July

$573

August

$534

September

$492

October

$490

November

$382

December

$406

Temperature and rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature and rainfall totals by month.

YWG

Temperature

3.2 - 68 °F

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated April 25, 2024.
See what other customers who have flown with Air Canada, Delta and WestJet from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,975 reviews
Check prices

Food

7.4

Boarding

8.2

Entertainment

8.0

Comfort

7.9

Overall

8.1

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta
8.1
Very good
10,975 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Food

7.4

Boarding

8.2

Entertainment

8.0

Comfort

7.9

Overall

8.1

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

WestJet
7.5
Good
2,985 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Food

7.4

Boarding

8.2

Entertainment

8.0

Comfort

7.9

Overall

8.1

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Porter Airlines
7.4
Good
438 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Food

7.4

Boarding

8.2

Entertainment

8.0

Comfort

7.9

Overall

8.1

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

United Airlines
7.4
Good
11,234 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Food

7.4

Boarding

8.2

Entertainment

8.0

Comfort

7.9

Overall

8.1

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Air Canada
7.0
Good
6,862 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Food

7.4

Boarding

8.2

Entertainment

8.0

Comfort

7.9

Overall

8.1

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 0 inbound flights from Chicago per day from 3 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • Can I find flights from Chicago to Winnipeg for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago to Winnipeg for under $400. The cheapest flight booked recently is on Multiple Airlines for just $330, but on average you can expect to pay $401.

  • Are there nonstop flights from Chicago to Winnipeg for under $700 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Winnipeg under $700. A good price for a nonstop flight from Chicago to Winnipeg is less than $853.

  • Are there last-minute flights available from Chicago to Winnipeg for under $400?

    There are currently 20+ open flights from Chicago to Winnipeg within the next 7 days for less than $400.

  • What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

    Flying on Delta is currently your cheapest option to Winnipeg, with prices starting at $398. Additional round-trip tickets that might be worth considering are offered by WestJet and Air Canada, with the lowest prices starting at $417 and $444, respectively. These flights start at 32% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

    One-way options have recently been found by users for as low as $202 on Delta. Other airlines that offer cheap prices include WestJet from $259 and Porter Airlines from $267 one-way.

  • What are the most popular airlines that fly from Chicago to Winnipeg?

    Before booking your flight from Chicago to Winnipeg check out the most popular airlines for this route: Air Canada, Delta or United Airlines.

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $862. On average you can expect to pay $956. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $375.

  • What does ORD to YWG mean?

    Chicago O'Hare Intl Airport is ORD and Winnipeg Airport is YWG. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Winnipeg that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Winnipeg flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Winnipeg with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Winnipeg flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Winnipeg that allow pets onboard?

    Many airlines flying from Chicago to Winnipeg offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Winnipeg?

    Yes, you can often find last-minute deals on Chicago to Winnipeg flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Winnipeg flight deals updated?

    The Chicago to Winnipeg flight deals you see on this page were last updated on 4/25.

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Alternative routes for Chicago to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.

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Top 3 airlines flying from Chicago to Winnipeg

Discover the top 3 airlines that operate flights from Chicago to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,068,701 searches. Data last updated April 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$164Average$531FlexibilityNo cancel feeOn-time67%
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DeltaCheapest$462Average$627FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapest$574Average$801FlexibilityNo cancel feeOn-time69%
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How does Cheapflights help users find flights from Chicago to Winnipeg?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Chicago to Winnipeg. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Winnipeg?

Cheapflights simply makes it quick and affordable to book flights from Chicago to Winnipeg by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Chicago to Winnipeg with no change fees?

Need flexible booking options for your flight to Winnipeg from Chicago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Chicago to Winnipeg become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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