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Cheap flights from Winnipeg to Chicago from C$ 223

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 5/6. 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
3 May — 10 May1
1 adult
Fri 3/5
Fri 10/5

The best prices from Winnipeg to Chicago are usually found in April or January, booked 23 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 28 April 2024.

Popular in

March

Cheapest in

April

Round-trip from

C$ 358

One-way from

C$ 260
High demand for flights, 14% potential price rise
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Best time to find cheap flights, 17% potential price drop
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From Winnipeg to Chicago (CHI)
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One-way flight from Winnipeg to Chicago (CHI)
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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 237% by booking at least 24 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$ 812.

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

The best pricing can be found in the month of April. Prices to Chicago from Winnipeg average C$ 727. You can even find prices in April for less than C$ 727, as users have found deals to Chicago from as low as C$ 470. The month of March 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 21% on airfare.

Cheap United Airlines flights from Winnipeg to Chicago

Explore cheap flight options specifically provided by United Airlines 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 490,828 searches. Data last updated 28 April 2024.
Check out some of the cheapest United Airlines flights we've come across from Winnipeg to Chicago. It's recommended that users confirm their flight details before booking.
Sat 25/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Wed 29/59:31 p.m.ORD - YWG
1 stop15h 40mUnited Airlines
Deal found 27/4C$ 556
Fri 24/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Fri 31/57:10 a.m.ORD - YWG
1 stop10h 45mUnited Airlines
Deal found 27/4C$ 610
Fri 24/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Mon 27/55:04 a.m.ORD - YWG
1 stop8h 07mUnited Airlines
Deal found 28/4C$ 675
Sat 25/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Wed 29/51:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 27/4C$ 677
Fri 24/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Mon 27/51:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 28/4C$ 734
Sat 25/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Wed 29/51:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 26/4C$ 735

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 490,828 searches. Data last updated 28 April 2024.
Browse through some of the cheapest WestJet 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.
Fri 24/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Fri 31/55:40 a.m.ORD - YWG
1 stop9h 45mWestJet
Deal found 27/4C$ 485
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 27/4C$ 492
Thu 30/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Fri 14/63:55 p.m.ORD - YWG
1 stop7h 34mWestJet
Deal found 27/4C$ 513
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Wed 29/57:00 a.m.ORD - YWG
1 stop8h 25mWestJet
Deal found 27/4C$ 514
Fri 24/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Fri 31/56:07 a.m.ORD - YWG
2 stops16h 36mWestJet
Deal found 27/4C$ 515
Sat 1/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Wed 12/66:00 a.m.ORD - YWG
1 stop17h 29mWestJet
Deal found 27/4C$ 519
Mon 27/56:30 a.m.YWG - ORD
2 stops16h 09mWestJet
Mon 3/69:36 a.m.ORD - YWG
2 stops13h 05mWestJet
Deal found 27/4C$ 523
Sat 1/66:50 a.m.YWG - ORD
2 stops14h 05mWestJet
Sat 15/66:00 a.m.ORD - YWG
2 stops16h 42mWestJet
Deal found 27/4C$ 525
Wed 8/58:00 a.m.YWG - ORD
1 stop15h 55mWestJet
Sun 12/56:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 28/4C$ 528

Cheap Winnipeg to Chicago flights in April & May 2024

Find cheap flight options from Winnipeg to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 490,828 searches. Prices were last updated on 28 April 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.
Wed 29/512:22 p.m.YWG - ORD
1 stop6h 48mDelta
Tue 18/63:55 p.m.ORD - YWG
1 stop7h 34mDelta
Deal found 27/4C$ 465
Fri 24/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Fri 31/55:40 a.m.ORD - YWG
1 stop9h 45mWestJet
Deal found 27/4C$ 485
Wed 29/52:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Mon 17/69:15 p.m.ORD - YWG
1 stop11h 37mAir Canada
Deal found 27/4C$ 489
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 27/4C$ 492
Thu 30/57:30 a.m.YWG - ORD
1 stop7h 24mAir Canada
Mon 17/69:15 p.m.ORD - YWG
1 stop11h 37mAir Canada
Deal found 27/4C$ 504
Wed 8/58:00 a.m.YWG - ORD
2 stops24h 55mMultiple Airlines
Sun 12/58:00 a.m.ORD - YWG
3 stops40h 44mMultiple Airlines
Deal found 28/4C$ 510
Thu 30/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Fri 14/63:55 p.m.ORD - YWG
1 stop7h 34mWestJet
Deal found 27/4C$ 513
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Wed 29/57:00 a.m.ORD - YWG
1 stop8h 25mWestJet
Deal found 27/4C$ 514
Fri 24/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Fri 31/56:07 a.m.ORD - YWG
2 stops16h 36mWestJet
Deal found 27/4C$ 515

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 490,828 searches. Data last updated 28 April 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.
Wed 29/512:22 p.m.YWG - ORD
1 stop6h 48mDelta
Tue 18/63:55 p.m.ORD - YWG
1 stop7h 34mDelta
Deal found 27/4C$ 465
Tue 4/66:55 a.m.YWG - ORD
2 stops5h 47mDelta
Tue 18/63:55 p.m.ORD - YWG
1 stop7h 34mDelta
Deal found 27/4C$ 477
Fri 24/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Fri 31/55:40 a.m.ORD - YWG
1 stop9h 45mWestJet
Deal found 27/4C$ 485
Wed 29/52:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Mon 17/69:15 p.m.ORD - YWG
1 stop11h 37mAir Canada
Deal found 27/4C$ 489
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sat 1/69:52 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 27/4C$ 492
Thu 30/57:30 a.m.YWG - ORD
1 stop7h 24mAir Canada
Mon 17/69:15 p.m.ORD - YWG
1 stop11h 37mAir Canada
Deal found 27/4C$ 504
Sat 1/66:55 a.m.YWG - ORD
2 stops9h 38mDelta
Sat 15/64:00 p.m.ORD - YWG
1 stop7h 29mDelta
Deal found 27/4C$ 507
Wed 8/58:00 a.m.YWG - ORD
2 stops24h 55mMultiple Airlines
Sun 12/58:00 a.m.ORD - YWG
3 stops40h 44mMultiple Airlines
Deal found 28/4C$ 510
Thu 30/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Thu 13/66:05 a.m.ORD - YWG
1 stop9h 20mWestJet
Deal found 27/4C$ 513

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 490,828 searches. Data last updated 28 April 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.
Sat 25/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Wed 29/51:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 27/4C$ 677
Fri 24/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Fri 31/51:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 27/4C$ 678
Fri 24/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Mon 27/51:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 28/4C$ 734
Sat 25/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Wed 29/51:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 26/4C$ 735
Mon 27/52:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sat 1/61:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 27/4C$ 903
Mon 27/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Mon 3/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 27/4C$ 996
Thu 30/52:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sun 2/61:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 27/4C$ 1,055
Wed 29/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Sun 16/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 27/4C$ 1,059
Sat 1/62:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Sat 15/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 27/4C$ 1,069

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 490,828 searches. Data last updated 28 April 2024.
Book one of these great deals on flights from Winnipeg to Chicago. Tip: verify your flight details before completing your reservation.
Wed 8/58:00 a.m.YWG - ORD
1 stop12h 35mMultiple Airlines
Sun 12/58:00 a.m.ORD - YWG
3 stops40h 44mMultiple Airlines
Deal found 28/4C$ 489
Wed 8/58:00 a.m.YWG - ORD
2 stops24h 55mMultiple Airlines
Sun 12/58:00 a.m.ORD - YWG
3 stops40h 44mMultiple Airlines
Deal found 28/4C$ 510
Wed 8/58:00 a.m.YWG - ORD
1 stop12h 35mMultiple Airlines
Sun 12/58:00 a.m.ORD - YWG
2 stops11h 48mMultiple Airlines
Deal found 28/4C$ 517
Wed 8/58:00 a.m.YWG - ORD
1 stop15h 55mWestJet
Sun 12/56:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 28/4C$ 528
Fri 3/55:35 p.m.YWG - ORD
1 stop21h 20mWestJet
Sun 12/56:07 a.m.ORD - YWG
1 stop17h 16mWestJet
Deal found 27/4C$ 543
Fri 3/55:35 p.m.YWG - ORD
1 stop23h 20mWestJet
Sun 12/56:07 a.m.ORD - YWG
2 stops16h 35mWestJet
Deal found 27/4C$ 548
Tue 30/412:30 p.m.YWG - ORD
1 stop9h 28mWestJet
Tue 14/55:57 p.m.ORD - YWG
2 stops27h 15mWestJet
Deal found 27/4C$ 556
Tue 30/46:30 a.m.YWG - ORD
2 stops15h 28mWestJet
Fri 3/56:20 a.m.ORD - YWG
2 stops16h 22mWestJet
Deal found 27/4C$ 564
Tue 30/45:35 p.m.YWG - ORD
1 stop4h 23mWestJet
Fri 3/511:45 a.m.ORD - YWG
2 stops12h 48mWestJet
Deal found 27/4C$ 567

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 490,828 searches. Data last updated 28 April 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.
Wed 5/68:00 a.m.YWG - ORD
1 stop12h 47mMultiple Airlines
Deal found 27/4C$ 223
Wed 29/58:00 a.m.YWG - MDW
1 stop6h 41mMultiple Airlines
Deal found 27/4C$ 226
Thu 30/58:00 a.m.YWG - MDW
1 stop9h 17mMultiple Airlines
Deal found 27/4C$ 231
Wed 29/58:00 a.m.YWG - ORD
1 stop8h 37mMultiple Airlines
Deal found 27/4C$ 231
Wed 12/68:00 a.m.YWG - ORD
1 stop8h 47mMultiple Airlines
Deal found 28/4C$ 234
Thu 30/58:00 a.m.YWG - ORD
1 stop8h 28mMultiple Airlines
Deal found 27/4C$ 236
Sat 1/68:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Deal found 27/4C$ 239
Wed 12/68:00 a.m.YWG - MDW
1 stop6h 34mMultiple Airlines
Deal found 28/4C$ 246
Fri 31/55:00 p.m.YWG - ORD
1 stop9h 00mMultiple Airlines
Deal found 27/4C$ 249

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 490,828 searches. Data last updated 28 April 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 465 - C$ 637

Route

Depart

Return

Price

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 29/5

1 stop6h 48m

Chicago O'Hare Intl

Sat 15/6

1 stop7h 29m

C$ 465

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Tue 4/6

2 stops11h 32m

Chicago O'Hare Intl

Sat 15/6

1 stop7h 29m

C$ 477

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Fri 24/5

1 stop8h 35m

Chicago O'Hare Intl

Fri 31/5

1 stop9h 45m

C$ 485

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 29/5

Nonstop2h 28m

Chicago O'Hare Intl

Mon 17/6

1 stop11h 37m

C$ 489

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 25/5

1 stop8h 35m

Chicago O'Hare Intl

Sat 1/6

2 stops12h 48m

C$ 492

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 30/5

1 stop7h 24m

Chicago O'Hare Intl

Mon 17/6

1 stop11h 37m

C$ 504

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 8/5

2 stops24h 55m

Chicago O'Hare Intl

Sun 12/5

3 stops40h 44m

C$ 510

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 25/5

Nonstop2h 28m

Chicago O'Hare Intl

Wed 29/5

1 stop15h 40m

C$ 556

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Mon 3/6

1 stop10h 17m

Chicago Midway

Fri 14/6

1 stop10h 55m

C$ 637

Flights are sorted by cheapest first

Deals found on 27/4

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 28 January 2024.
The best time to book flights from Winnipeg to Chicago is 23 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 21 April 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. Tuesday evenings 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 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$ 235 while a round-trip flight costs C$ 513. Price data was last updated on 21 April 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$ 452). 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$ 357

February

C$ 416

March

C$ 443

April

C$ 455

May

C$ 536

June

C$ 560

July

C$ 605

August

C$ 618

September

C$ 473

October

C$ 508

November

C$ 462

December

C$ 477

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 28 April 2024.
Get a feel of what it's like to fly with United Airlines, WestJet 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
8.1
Very good
10,932 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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

Delta
8.1
Very good
10,932 reviews
Delta
8.1
Very good
10,932 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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

Austrian Airlines
7.7
Good
1,083 reviews
Delta
8.1
Very good
10,932 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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

WestJet
7.5
Good
2,977 reviews
Delta
8.1
Very good
10,932 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

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
10,932 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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

United Airlines
7.4
Good
11,221 reviews
Delta
8.1
Very good
10,932 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

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 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 Delta for just C$ 465, but on average you can expect to pay C$ 507.

  • 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$ 1,092.

  • Are there last-minute flights available from Winnipeg to Chicago for under C$ 500?

    There are currently 20+ open flights from Winnipeg to Chicago within the next 7 days for less than C$ 500.

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

    Delta, at C$ 465, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include WestJet and Air Canada. Delta 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$ 239. However, be on the lookout for offers from Air Canada and Delta, 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$ 267. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 465 on average our data indicates C$ 838 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 28/4.

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Alternative routes for Winnipeg to Chicago
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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 490,828 searches. Data last updated 28 April 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 388AverageC$ 651FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Endeavor AirlinesCheapestC$ 462AverageC$ 823FlexibilityNo cancel feeOn-timeN/A
Search Endeavor Airlines flights
DeltaCheapestC$ 481AverageC$ 664FlexibilityNo cancel feeOn-timeN/A
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WestJetCheapestC$ 560AverageC$ 795FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 596AverageC$ 774FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJet EncoreCheapestC$ 783AverageC$ 800FlexibilityNo 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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