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Cheap flights from Winnipeg to Chicago from C$ 198

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 1/6. 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.
YWG — CHI
23 May — 30 May1
1 adult
Thu 23/5
Thu 30/5

The best prices from Winnipeg to Chicago are usually found in November or March, booked 16 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Winnipeg to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Chicago (CHI). 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 18 May 2024.

Popular in

August

Cheapest in

November

Average price

C$ 639

Round-trip from

C$ 351
High demand for flights, 14% potential price rise
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Best time to find cheap flights, 12% potential price drop
Search Deals
Average for round-trip flights in May 2024
Search Deals
From Winnipeg to Chicago (CHI)
Search Deals

What is the cheapest day to fly round-trip from Winnipeg to Chicago?

Monday is generally a great day to depart. Flying on this day could help you save up to 19%.

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

Find a great deal and save up to 115% by booking at least 17 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Winnipeg to Chicago within the next two weeks, with the cheapest ticket starting at C$ 742.

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

The best pricing can be found in the month of November. Prices to Chicago from Winnipeg average C$ 700. You can even find prices in November for less than C$ 700, as users have found deals to Chicago from as low as C$ 370. The month of August appears to be one of the more expensive times to travel to Chicago from Winnipeg. Flying in the targeted month can save you up to 16%.

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

One of the essential ways to save on airfare from Winnipeg to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 13% on airfare.

Cheap WestJet flights from Winnipeg to Chicago

Explore cheap flight options specifically provided by WestJet for the route between Winnipeg and Chicago. 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 407,867 searches. Data last updated 18 May 2024.
Check out some of the cheapest WestJet flights we've come across from Winnipeg to Chicago. It's recommended that users confirm their flight details before booking.
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/65:55 p.m.ORD - YWG
1 stop17h 47mWestJet
Deal found 17/5C$ 364
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 17/5C$ 406
Wed 29/512:22 p.m.YWG - ORD
1 stop10h 17mWestJet
Sun 2/66:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 17/5C$ 441
Sat 15/66:55 a.m.YWG - ORD
1 stop8h 10mWestJet
Mon 17/68:35 p.m.ORD - YWG
1 stop26h 54mWestJet
Deal found 17/5C$ 445
Tue 4/66:30 a.m.YWG - ORD
2 stops16h 11mWestJet
Sat 8/69:20 a.m.ORD - YWG
1 stop14h 09mWestJet
Deal found 17/5C$ 447
Fri 28/66:55 a.m.YWG - ORD
1 stop15h 02mWestJet
Tue 2/79:20 a.m.ORD - YWG
1 stop14h 27mWestJet
Deal found 16/5C$ 448
Wed 29/57:30 a.m.YWG - ORD
2 stops9h 19mWestJet
Sun 2/66:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 17/5C$ 455
Mon 27/58:15 p.m.YWG - ORD
2 stops20h 18mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 17/5C$ 459
Thu 30/58:50 p.m.YWG - ORD
1 stop20h 15mWestJet
Sun 2/66:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 17/5C$ 460

Cheap Delta flights from Winnipeg to Chicago

Explore cheap flight options specifically provided by Delta for the route between Winnipeg and Chicago. 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 407,867 searches. Data last updated 18 May 2024.
Browse through some of the cheapest Delta flights travelling from Winnipeg to Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Tue 28/56:55 a.m.YWG - ORD
1 stop7h 47mDelta
Fri 31/59:36 a.m.ORD - YWG
1 stop7h 09mDelta
Deal found 17/5C$ 458
Tue 30/76:55 a.m.YWG - ORD
1 stop7h 49mDelta
Mon 5/87:10 a.m.ORD - YWG
1 stop8h 12mDelta
Deal found 17/5C$ 610
Wed 18/97:30 a.m.YWG - ORD
2 stops11h 10mDelta
Tue 24/91:35 p.m.ORD - YWG
2 stops9h 46mDelta
Deal found 17/5C$ 655
Thu 30/512:22 p.m.YWG - MDW
1 stop5h 45mDelta
Sun 2/69:32 a.m.MDW - YWG
2 stops11h 40mDelta
Deal found 18/5C$ 685
Thu 30/512:22 p.m.YWG - MDW
1 stop5h 45mDelta
Sun 2/69:32 a.m.MDW - YWG
2 stops11h 40mDelta
Deal found 17/5C$ 874
Thu 30/56:55 a.m.YWG - MDW
2 stops5h 45mDelta
Sun 2/69:32 a.m.MDW - YWG
2 stops11h 40mDelta
Deal found 18/5C$ 885

Cheap Winnipeg to Chicago flights in May & June 2024

Find cheap flight options from Winnipeg to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 407,867 searches. Prices were last updated on 18 May 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/65:55 p.m.ORD - YWG
1 stop17h 47mWestJet
Deal found 17/5C$ 364
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 17/5C$ 406
Wed 29/512:22 p.m.YWG - ORD
1 stop10h 17mWestJet
Sun 2/66:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 17/5C$ 441
Sat 15/66:55 a.m.YWG - ORD
1 stop8h 10mWestJet
Mon 17/68:35 p.m.ORD - YWG
1 stop26h 54mWestJet
Deal found 17/5C$ 445
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/59:36 a.m.ORD - YWG
1 stop25h 55mWestJet
Deal found 17/5C$ 447
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/55:44 p.m.ORD - YWG
1 stop5h 39mWestJet
Deal found 16/5C$ 448
Tue 28/56:30 a.m.YWG - ORD
2 stops10h 19mMultiple Airlines
Fri 31/59:36 a.m.ORD - YWG
1 stop7h 09mMultiple Airlines
Deal found 17/5C$ 454
Sat 25/57:30 a.m.YWG - MDW
2 stops8h 43mWestJet
Wed 29/58:45 a.m.MDW - YWG
1 stop6h 40mWestJet
Deal found 16/5C$ 455
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/59:36 a.m.ORD - YWG
2 stops14h 21mWestJet
Deal found 16/5C$ 455

Winnipeg to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Winnipeg and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 407,867 searches. Data last updated 18 May 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/65:55 p.m.ORD - YWG
1 stop17h 47mWestJet
Deal found 17/5C$ 364
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 17/5C$ 406
Wed 29/512:22 p.m.YWG - ORD
1 stop10h 17mWestJet
Sun 2/66:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 17/5C$ 441
Sat 15/66:55 a.m.YWG - ORD
1 stop8h 10mWestJet
Mon 17/68:35 p.m.ORD - YWG
1 stop26h 54mWestJet
Deal found 17/5C$ 445
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/59:36 a.m.ORD - YWG
1 stop25h 55mWestJet
Deal found 17/5C$ 447
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/55:44 p.m.ORD - YWG
1 stop5h 39mWestJet
Deal found 16/5C$ 448
Tue 28/56:30 a.m.YWG - ORD
2 stops10h 19mMultiple Airlines
Fri 31/59:36 a.m.ORD - YWG
1 stop7h 09mMultiple Airlines
Deal found 17/5C$ 454
Sat 25/57:30 a.m.YWG - MDW
2 stops8h 43mWestJet
Wed 29/58:45 a.m.MDW - YWG
1 stop6h 40mWestJet
Deal found 16/5C$ 455
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/59:36 a.m.ORD - YWG
2 stops14h 21mWestJet
Deal found 16/5C$ 455

Direct flights to Chicago from Winnipeg

Discover non-stop flight options from Winnipeg to Chicago. 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 407,867 searches. Data last updated 18 May 2024.
Consider booking one of these non-stop flights heading from Winnipeg to Chicago. Those looking to potentially save on 1 or 2-stop flights from Winnipeg to Chicago should utilize the search form at the top of the page.
Wed 2/102:20 p.m.YWG - ORD
Nonstop2h 32mUnited Airlines
Wed 6/111:00 p.m.ORD - YWG
Nonstop2h 24mUnited Airlines
Deal found 17/5C$ 726
Wed 18/92:24 p.m.YWG - ORD
Nonstop2h 32mAir Canada
Tue 24/91:05 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 17/5C$ 786
Thu 12/92:24 p.m.YWG - ORD
Nonstop2h 32mAir Canada
Sun 15/91:05 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 18/5C$ 839
Sun 16/62:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sun 23/61:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 17/5C$ 880
Tue 4/62:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sat 8/61:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 17/5C$ 887
Sat 28/92:20 p.m.YWG - ORD
Nonstop2h 32mUnited Airlines
Mon 30/91:05 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 16/5C$ 929
Tue 30/72:25 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sun 4/81:15 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 17/5C$ 970
Fri 28/62:25 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Mon 1/71:15 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 17/5C$ 1,042
Tue 30/72:25 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Mon 5/81:15 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 17/5C$ 1,064

Winnipeg to Chicago flights leaving soon

Find last-minute flight options from Winnipeg to Chicago 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 407,867 searches. Data last updated 18 May 2024.
Book one of these great deals on flights from Winnipeg to Chicago. Tip: verify your flight details before completing your reservation.
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/65:55 p.m.ORD - YWG
1 stop17h 47mWestJet
Deal found 17/5C$ 364
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 17/5C$ 406
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Tue 28/53:50 p.m.ORD - YWG
2 stops21h 29mWestJet
Deal found 17/5C$ 441
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/59:36 a.m.ORD - YWG
1 stop25h 55mWestJet
Deal found 17/5C$ 447
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/55:44 p.m.ORD - YWG
1 stop5h 39mWestJet
Deal found 16/5C$ 448
Tue 28/56:30 a.m.YWG - ORD
2 stops10h 19mMultiple Airlines
Fri 31/59:36 a.m.ORD - YWG
1 stop7h 09mMultiple Airlines
Deal found 17/5C$ 454
Sat 25/57:30 a.m.YWG - MDW
2 stops8h 43mWestJet
Wed 29/58:45 a.m.MDW - YWG
1 stop6h 40mWestJet
Deal found 16/5C$ 455
Sat 25/56:55 a.m.YWG - ORD
1 stop14h 42mWestJet
Wed 29/59:36 a.m.ORD - YWG
2 stops14h 21mWestJet
Deal found 16/5C$ 455
Tue 28/56:55 a.m.YWG - ORD
1 stop7h 47mDelta
Fri 31/59:36 a.m.ORD - YWG
1 stop7h 09mDelta
Deal found 17/5C$ 458

One-way flights to Chicago from Winnipeg

Search for one-way flight options from Winnipeg to Chicago. 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 407,867 searches. Data last updated 18 May 2024.
Users in need of a one-way flight from Winnipeg to Chicago can choose from these deals. For those needing a return trip from Winnipeg, there is a search form available above.
Sat 1/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Deal found 16/5C$ 198
Sat 1/66:55 a.m.YWG - ORD
2 stops5h 47mDelta
Deal found 16/5C$ 230
Fri 2/812:22 p.m.YWG - ORD
2 stops11h 32mDelta
Deal found 17/5C$ 304
Sun 28/76:05 p.m.YWG - ORD
3 stops25h 54mMultiple Airlines
Deal found 17/5C$ 311
Sun 28/78:00 a.m.YWG - ORD
1 stop12h 47mMultiple Airlines
Deal found 17/5C$ 317
Fri 2/87:50 p.m.YWG - MDW
2 stops22h 33mWestJet
Deal found 17/5C$ 320
Sun 28/79:35 a.m.YWG - ORD
2 stops32h 49mWestJet
Deal found 17/5C$ 331
Fri 2/88:00 a.m.YWG - MDW
1 stop6h 57mDelta
Deal found 17/5C$ 335
Sun 14/77:50 p.m.YWG - ORD
2 stops28h 04mWestJet
Deal found 18/5C$ 347

Find flights from Winnipeg to Chicago within your budget

Customize your flight search to find flights from Winnipeg to Chicago 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 407,867 searches. Data last updated 18 May 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 441 - C$ 829

Route

Depart

Return

Price

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 29/5

1 stop10h 17m

Chicago O'Hare Intl

Sun 2/6

1 stop17h 16m

C$ 441

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 15/6

1 stop8h 10m

Chicago O'Hare Intl

Mon 17/6

1 stop26h 54m

C$ 445

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Tue 4/6

2 stops16h 11m

Chicago O'Hare Intl

Sat 8/6

1 stop14h 09m

C$ 447

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Tue 28/5

2 stops10h 19m

Chicago O'Hare Intl

Fri 31/5

1 stop7h 09m

C$ 454

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Tue 28/5

1 stop7h 47m

Chicago O'Hare Intl

Fri 31/5

1 stop7h 09m

C$ 458

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Tue 28/5

1 stop5h 45m

Chicago Midway

Fri 31/5

1 stop13h 13m

C$ 481

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Fri 14/6

Nonstop2h 28m

Chicago O'Hare Intl

Mon 17/6

1 stop11h 37m

C$ 632

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Fri 28/6

Nonstop2h 28m

Chicago O'Hare Intl

Tue 2/7

1 stop8h 05m

C$ 681

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Tue 28/5

2 stops9h 12m

Chicago Midway

Fri 31/5

3 stops24h 52m

C$ 829

Flights are sorted by cheapest first

Deals found on 17/5

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

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Chicago. Price data was last updated on 10 May 2024.
The best time to book flights from Winnipeg to Chicago is 16 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Search Deals

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

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Chicago. Price data was last updated on 12 May 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Winnipeg to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Chicago by month

Plan your trip from Winnipeg to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Winnipeg to Chicago is currently C$ 299 while a round-trip flight costs C$ 541. Price data was last updated on 12 May 2024.

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 261). Flying from Winnipeg to Chicago in August is currently the most expensive (average of C$ 440). 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

C$ 356

February

C$ 414

March

C$ 441

April

C$ 454

May

C$ 477

June

C$ 550

July

C$ 591

August

C$ 599

September

C$ 466

October

C$ 508

November

C$ 460

December

C$ 475

Temperature and rainfall in Chicago by month

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

CHI

Temperature

-5 - 23 °C

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 18 May 2024.
Get a feel of what it's like to fly with WestJet, Delta and Air Canada from Winnipeg to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,647 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,647 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Aeromexico
7.6
Good
2,525 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.5
Good
2,899 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Porter Airlines
7.4
Good
414 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

United Airlines
7.4
Good
10,906 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Chicago. 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 from for flights from Winnipeg to Chicago?

    If you book a flight to Chicago from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 0 flights from Winnipeg to Chicago per day from 6 different airlines.

  • Can I find flights from Winnipeg to Chicago for under C$ 500 on Cheapflights?

    Yes, there are multiple flights from Winnipeg to Chicago for under C$ 500. The cheapest flight booked recently is on WestJet for just C$ 441, but on average you can expect to pay C$ 479.

  • Are there direct flights from Winnipeg to Chicago for under C$ 800 on Cheapflights?

    Cheapflights has 20 direct flights from Winnipeg to Chicago under C$ 800. A good price for a direct flight from Winnipeg to Chicago is less than C$ 1,084.

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

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

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

    WestJet, at C$ 441, was found to be the cheapest airline from Winnipeg to Chicago. An alternate airline flying to your destination would be Delta. WestJet is priced at 36% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 198. However, be on the lookout for offers from Delta and United Airlines, as they are both options that can get you from Winnipeg to Chicago for a low price.

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

    Endeavor Airlines, Air Canada and Delta are the most popular airlines when flying from Winnipeg to Chicago.

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 374. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 384 on average our data indicates C$ 741 when flying from Winnipeg to Chicago.

  • What does YWG to ORD mean?

    Great question - YWG to ORD just means Winnipeg Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

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

    The amount of baggage you can bring on your Winnipeg to Chicago 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 Winnipeg to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Winnipeg to Chicago 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 Winnipeg to Chicago that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Chicago 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 Winnipeg to Chicago that allow pets onboard?

    Many airlines flying from Winnipeg to Chicago 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 Winnipeg to Chicago?

    Yes, you can often find last-minute deals on Winnipeg to Chicago 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 Winnipeg to Chicago flight deals updated?

    The Winnipeg to Chicago flight deals you see on this page were last updated on 17/5.

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

Winnipeg to O'Hare Intl flights

Top 6 airlines flying from Winnipeg to Chicago

Discover the top 6 airlines that operate flights from Winnipeg to Chicago. 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 407,867 searches. Data last updated 18 May 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 388AverageC$ 648FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Endeavor AirlinesCheapestC$ 460AverageC$ 820FlexibilityNo cancel feeOn-timeN/A
Search Endeavor Airlines flights
DeltaCheapestC$ 477AverageC$ 665FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 603AverageC$ 795FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 654AverageC$ 880FlexibilityNo cancel feeOn-time60%
Search WestJet flights
WestJet EncoreCheapestC$ 781AverageC$ 798FlexibilityNo cancel feeOn-timeN/A
Search WestJet Encore flights
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How does Cheapflights help users find flights from Winnipeg to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Winnipeg today with Cheapflights!

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

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Winnipeg.

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

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Chicago, users can toggle the no change fees filter when performing a flight search.

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

Yes, Cheapflights offers price alerts on Winnipeg to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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