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Cheap flights from Winnipeg to Chicago from C$ 214

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 2/8. 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
21 May — 28 May1
1 adult
Tue 21/5
Tue 28/5

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 16 May 2024.

Popular in

August

Cheapest in

November

Round-trip from

C$ 351

One-way from

C$ 311
High demand for flights, 14% potential price rise
Best time to find cheap flights, 12% potential price drop
From Winnipeg to Chicago (CHI)
One-way flight from Winnipeg to Chicago (CHI)

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$ 743.

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$ 701. You can even find prices in November for less than C$ 701, as users have found deals to Chicago from as low as C$ 371. 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 409,532 searches. Data last updated 16 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 15/5C$ 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 15/5C$ 403
Mon 3/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Tue 11/69:20 a.m.ORD - YWG
1 stop14h 09mWestJet
Deal found 15/5C$ 422
Mon 3/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Tue 11/69:20 a.m.ORD - YWG
1 stop14h 09mWestJet
Deal found 15/5C$ 426
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mWestJet
Deal found 14/5C$ 433
Wed 29/53:20 p.m.YWG - ORD
1 stop25h 45mWestJet
Fri 31/55:40 a.m.ORD - YWG
1 stop9h 45mWestJet
Deal found 16/5C$ 435
Wed 29/56:55 a.m.YWG - ORD
1 stop15h 44mWestJet
Sun 2/66:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 15/5C$ 440
Wed 29/55:35 p.m.YWG - ORD
1 stop5h 04mWestJet
Fri 31/57:09 a.m.ORD - YWG
2 stops14h 03mWestJet
Deal found 16/5C$ 441
Mon 3/69:35 a.m.YWG - ORD
2 stops11h 20mWestJet
Tue 11/69:20 a.m.ORD - YWG
2 stops14h 37mWestJet
Deal found 15/5C$ 444

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 409,532 searches. Data last updated 16 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.
Mon 3/65:35 p.m.YWG - ORD
1 stop5h 06mDelta
Tue 11/68:30 a.m.ORD - YWG
2 stops14h 59mDelta
Deal found 15/5C$ 383
Sat 15/66:55 a.m.YWG - ORD
1 stop8h 10mDelta
Sat 22/61:25 p.m.ORD - YWG
2 stops10h 04mDelta
Deal found 16/5C$ 384
Sat 25/57:30 a.m.YWG - ORD
2 stops9h 03mDelta
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mDelta
Deal found 15/5C$ 455
Sat 25/56:55 a.m.YWG - MDW
1 stop4h 07mDelta
Wed 29/57:10 p.m.MDW - YWG
1 stop4h 13mDelta
Deal found 15/5C$ 531
Mon 22/76:55 a.m.YWG - ORD
1 stop7h 49mDelta
Mon 23/97:10 a.m.ORD - YWG
2 stops16h 11mDelta
Deal found 15/5C$ 540
Wed 18/96:55 a.m.YWG - MDW
1 stop6h 07mDelta
Tue 24/96:45 p.m.MDW - YWG
1 stop4h 36mDelta
Deal found 15/5C$ 549
Tue 1/106:55 a.m.YWG - ORD
1 stop8h 01mDelta
Tue 8/101:35 p.m.ORD - YWG
2 stops9h 46mDelta
Deal found 15/5C$ 550
Thu 13/67:30 a.m.YWG - MDW
2 stops9h 34mDelta
Thu 20/69:34 a.m.MDW - YWG
2 stops13h 55mDelta
Deal found 16/5C$ 554
Wed 22/56:55 a.m.YWG - MDW
2 stops5h 45mDelta
Mon 27/58:45 a.m.MDW - YWG
2 stops14h 38mDelta
Deal found 15/5C$ 561

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 409,532 searches. Prices were last updated on 16 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 15/5C$ 364
Mon 3/65:35 p.m.YWG - ORD
1 stop5h 06mDelta
Tue 11/68:30 a.m.ORD - YWG
2 stops14h 59mDelta
Deal found 15/5C$ 383
Sat 25/56:55 a.m.YWG - ORD
1 stop4h 30mDelta
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mDelta
Deal found 15/5C$ 384
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 15/5C$ 403
Mon 3/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Tue 11/69:20 a.m.ORD - YWG
1 stop14h 09mWestJet
Deal found 15/5C$ 422
Mon 3/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Tue 11/69:20 a.m.ORD - YWG
1 stop14h 09mWestJet
Deal found 15/5C$ 426
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mWestJet
Deal found 14/5C$ 433
Wed 29/53:20 p.m.YWG - ORD
1 stop25h 45mWestJet
Fri 31/55:40 a.m.ORD - YWG
1 stop9h 45mWestJet
Deal found 16/5C$ 435
Wed 29/56:55 a.m.YWG - ORD
1 stop15h 44mWestJet
Sun 2/66:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 15/5C$ 440

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 409,532 searches. Data last updated 16 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 15/5C$ 364
Mon 3/65:35 p.m.YWG - ORD
1 stop5h 06mDelta
Tue 11/68:30 a.m.ORD - YWG
2 stops14h 59mDelta
Deal found 15/5C$ 383
Sat 25/56:55 a.m.YWG - ORD
1 stop4h 30mDelta
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mDelta
Deal found 15/5C$ 384
Mon 27/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 15/5C$ 403
Mon 3/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Tue 11/69:20 a.m.ORD - YWG
1 stop14h 09mWestJet
Deal found 15/5C$ 422
Mon 3/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Tue 11/69:20 a.m.ORD - YWG
1 stop14h 09mWestJet
Deal found 15/5C$ 426
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mWestJet
Deal found 14/5C$ 433
Wed 29/53:20 p.m.YWG - ORD
1 stop25h 45mWestJet
Fri 31/55:40 a.m.ORD - YWG
1 stop9h 45mWestJet
Deal found 16/5C$ 435
Wed 29/56:55 a.m.YWG - ORD
1 stop15h 44mWestJet
Sun 2/66:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 15/5C$ 440

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 409,532 searches. Data last updated 16 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.
Fri 14/62:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Fri 21/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 15/5C$ 663
Thu 13/62:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Thu 20/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 14/5C$ 721
Wed 18/92:24 p.m.YWG - ORD
Nonstop2h 32mUnited Airlines
Wed 25/91:05 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 15/5C$ 737
Tue 11/62:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Tue 18/61:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 15/5C$ 783
Wed 18/92:24 p.m.YWG - ORD
Nonstop2h 32mAir Canada
Tue 24/91:05 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 16/5C$ 786
Sat 15/62:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Sat 22/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 16/5C$ 796
Thu 13/62:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Thu 20/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 16/5C$ 808
Sun 8/92:24 p.m.YWG - ORD
Nonstop2h 32mUnited Airlines
Fri 13/91:05 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 16/5C$ 809
Thu 13/62:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Thu 20/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 16/5C$ 839

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 409,532 searches. Data last updated 16 May 2024.
Book one of these great deals on flights from Winnipeg to Chicago. Tip: verify your flight details before completing your reservation.
Sat 25/56:55 a.m.YWG - ORD
1 stop4h 30mDelta
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mDelta
Deal found 15/5C$ 384
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mWestJet
Deal found 14/5C$ 433
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Wed 29/59:36 a.m.ORD - YWG
2 stops14h 21mWestJet
Deal found 14/5C$ 441
Sat 25/57:30 a.m.YWG - MDW
2 stops27h 32mWestJet
Wed 29/54:41 p.m.MDW - YWG
1 stop22h 44mWestJet
Deal found 14/5C$ 454
Wed 22/57:30 a.m.YWG - ORD
2 stops9h 03mWestJet
Mon 27/56:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 15/5C$ 454
Sat 25/57:30 a.m.YWG - MDW
2 stops25h 21mWestJet
Wed 29/512:42 p.m.MDW - YWG
1 stop26h 43mWestJet
Deal found 15/5C$ 455
Sat 25/57:30 a.m.YWG - ORD
2 stops9h 03mDelta
Wed 29/53:50 p.m.ORD - YWG
1 stop7h 33mDelta
Deal found 15/5C$ 455
Wed 22/54:20 p.m.YWG - ORD
1 stop24h 45mWestJet
Mon 27/55:55 p.m.ORD - YWG
1 stop26h 08mWestJet
Deal found 15/5C$ 456
Sat 25/57:30 a.m.YWG - ORD
2 stops14h 07mWestJet
Wed 29/59:36 a.m.ORD - YWG
2 stops14h 21mWestJet
Deal found 14/5C$ 462

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 409,532 searches. Data last updated 16 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.
Fri 2/88:30 a.m.YWG - ORD
1 stop8h 27mWestJet
Deal found 16/5C$ 214
Fri 5/78:00 a.m.YWG - ORD
1 stop8h 47mMultiple Airlines
Deal found 15/5C$ 230
Thu 4/78:00 a.m.YWG - MDW
1 stop9h 01mMultiple Airlines
Deal found 15/5C$ 245
Thu 4/76:55 a.m.YWG - ORD
1 stop8h 06mDelta
Deal found 15/5C$ 245
Fri 13/98:00 a.m.YWG - MDW
1 stop12h 49mMultiple Airlines
Deal found 16/5C$ 252
Thu 4/76:55 a.m.YWG - MDW
2 stops14h 51mDelta
Deal found 15/5C$ 253
Fri 13/98:00 a.m.YWG - ORD
1 stop8h 31mMultiple Airlines
Deal found 16/5C$ 259
Thu 27/66:55 a.m.YWG - ORD
1 stop15h 02mWestJet
Deal found 16/5C$ 260
Thu 4/76:30 a.m.YWG - MDW
2 stops12h 01mWestJet
Deal found 15/5C$ 263

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 409,532 searches. Data last updated 16 May 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 364 - C$ 663

Route

Depart

Return

Price

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 27/5

1 stop8h 35m

Chicago O'Hare Intl

Sat 1/6

1 stop17h 47m

C$ 364

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 3/6

1 stop5h 06m

Chicago O'Hare Intl

Tue 11/6

2 stops14h 59m

C$ 383

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 15/6

1 stop8h 10m

Chicago O'Hare Intl

Sat 22/6

2 stops10h 04m

C$ 384

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 27/5

1 stop8h 35m

Chicago O'Hare Intl

Sat 1/6

2 stops12h 48m

C$ 403

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 3/6

1 stop8h 35m

Chicago O'Hare Intl

Tue 11/6

1 stop14h 09m

C$ 422

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Fri 14/6

Nonstop2h 28m

Chicago O'Hare Intl

Fri 21/6

1 stop11h 37m

C$ 535

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 13/6

2 stops16h 55m

Chicago O'Hare Intl

Thu 20/6

3 stops22h 31m

C$ 538

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Thu 13/6

1 stop15h 37m

Chicago Midway

Thu 20/6

1 stop14h 20m

C$ 639

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Fri 14/6

Nonstop2h 28m

Chicago O'Hare Intl

Fri 21/6

Nonstop2h 26m

C$ 663

Flights are sorted by cheapest first

Deals found on 15/5

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$ 247 while a round-trip flight costs C$ 481. 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 16 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.
8.0
Very good
10,673 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

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.

8.0
Very good
10,673 reviews
8.0
Very good
10,673 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

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.

7.6
Good
2,528 reviews
8.0
Very good
10,673 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

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.

7.5
Good
2,919 reviews
8.0
Very good
10,673 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

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.

7.4
Good
415 reviews
8.0
Very good
10,673 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

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.

7.4
Good
10,924 reviews
8.0
Very good
10,673 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

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$ 400 on Cheapflights?

    Yes, there are multiple flights from Winnipeg to Chicago for under C$ 400. The cheapest flight booked recently is on WestJet for just C$ 364, but on average you can expect to pay C$ 435.

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

    Cheapflights has 20 direct flights from Winnipeg to Chicago under C$ 700. A good price for a direct flight from Winnipeg to Chicago is less than C$ 888.

  • 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$ 364, 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 48% lower than the current average price of a flight leaving 3 months from now.

  • What are the most popular airlines that fly 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$ 353 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 16/5.

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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.

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 409,532 searches. Data last updated 16 May 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 389AverageC$ 649FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Endeavor AirlinesCheapestC$ 460AverageC$ 821FlexibilityNo cancel feeOn-timeN/A
Search Endeavor Airlines flights
DeltaCheapestC$ 477AverageC$ 665FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 604AverageC$ 795FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 654AverageC$ 881FlexibilityNo cancel feeOn-time60%
Search WestJet flights
WestJet EncoreCheapestC$ 781AverageC$ 798FlexibilityNo cancel feeOn-timeN/A
Search WestJet Encore flights

Search flights from Winnipeg to Chicago by cabin class

Find flights from Winnipeg to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.

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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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