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Cheap flights from Winnipeg to Chicago from C$ 357

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 14/7. 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 Apr — 30 Apr1
1 adult
Tue 23/4
Tue 30/4

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 Wednesday

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 April 2024.

Popular in

March

Cheapest in

April

Average price

C$ 611

Round-trip from

C$ 361
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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Average for round-trip flights in April 2024
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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$ 820.

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$ 734. You can even find prices in April for less than C$ 734, as users have found deals to Chicago from as low as C$ 475. 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 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 506,061 searches. Data last updated 18 April 2024.
Check out some of the cheapest Delta flights we've come across from Winnipeg to Chicago. It's recommended that users confirm their flight details before booking.
Mon 17/68:30 a.m.YWG - ORD
1 stop8h 27mDelta
Tue 25/67:05 a.m.ORD - YWG
2 stops16h 24mDelta
Deal found 17/4C$ 570
Wed 5/66:55 a.m.YWG - ORD
2 stops9h 38mDelta
Fri 7/68:30 a.m.ORD - YWG
2 stops14h 59mDelta
Deal found 17/4C$ 606
Fri 27/98:30 a.m.YWG - ORD
1 stop8h 39mDelta
Tue 1/101:35 p.m.ORD - YWG
2 stops9h 46mDelta
Deal found 17/4C$ 635
Thu 25/78:30 a.m.YWG - ORD
1 stop8h 27mDelta
Sat 27/71:25 p.m.ORD - YWG
2 stops10h 00mDelta
Deal found 17/4C$ 636
Mon 26/88:00 a.m.YWG - ORD
1 stop11h 01mDelta
Sat 31/83:50 p.m.ORD - YWG
1 stop7h 31mDelta
Deal found 17/4C$ 643
Fri 3/57:00 a.m.YWG - ORD
1 stop7h 55mDelta
Sun 12/59:36 a.m.ORD - YWG
1 stop7h 09mDelta
Deal found 17/4C$ 654
Fri 17/58:30 a.m.YWG - ORD
1 stop8h 35mDelta
Sun 26/59:52 a.m.ORD - YWG
1 stop25h 39mDelta
Deal found 17/4C$ 691
Sat 3/86:55 a.m.YWG - ORD
1 stop8h 12mDelta
Tue 6/87:10 a.m.ORD - YWG
2 stops16h 11mDelta
Deal found 16/4C$ 701
Mon 26/88:30 a.m.YWG - ORD
1 stop8h 27mDelta
Mon 2/97:10 a.m.ORD - YWG
1 stop8h 17mDelta
Deal found 17/4C$ 715

Cheap Air Canada flights from Winnipeg to Chicago

Explore cheap flight options specifically provided by Air Canada 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 506,061 searches. Data last updated 18 April 2024.
Browse through some of the cheapest Air Canada 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 27/52:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sat 1/66:00 a.m.ORD - YWG
1 stop10h 00mAir Canada
Deal found 17/4C$ 651
Fri 16/85:00 a.m.YWG - ORD
1 stop7h 54mAir Canada
Sat 24/86:00 a.m.ORD - YWG
1 stop9h 57mAir Canada
Deal found 17/4C$ 686
Thu 25/75:00 a.m.YWG - ORD
1 stop7h 54mAir Canada
Sat 27/74:00 p.m.ORD - YWG
1 stop8h 07mAir Canada
Deal found 17/4C$ 694
Thu 30/55:00 a.m.YWG - ORD
1 stop7h 54mAir Canada
Sun 2/69:15 p.m.ORD - YWG
1 stop11h 40mAir Canada
Deal found 17/4C$ 740
Sat 25/52:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sun 26/51:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 17/4C$ 756
Sat 28/92:15 p.m.YWG - ORD
Nonstop2h 21mAir Canada
Tue 1/108:35 a.m.ORD - YWG
1 stop6h 35mAir Canada
Deal found 17/4C$ 782
Tue 7/58:15 a.m.YWG - ORD
1 stop6h 26mAir Canada
Wed 8/56:00 a.m.ORD - YWG
1 stop10h 00mAir Canada
Deal found 16/4C$ 818
Thu 16/55:10 a.m.YWG - ORD
1 stop7h 50mAir Canada
Sun 19/56:00 a.m.ORD - YWG
1 stop10h 00mAir Canada
Deal found 17/4C$ 829
Fri 27/92:15 p.m.YWG - ORD
Nonstop2h 21mAir Canada
Mon 30/99:18 p.m.ORD - YWG
1 stop11h 36mAir Canada
Deal found 17/4C$ 835

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 506,061 searches. Prices were last updated on 18 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 24/47:30 a.m.YWG - ORD
1 stop9h 57mMultiple Airlines
Mon 29/48:05 p.m.ORD - YWG
2 stops23h 43mMultiple Airlines
Deal found 15/4C$ 542
Fri 3/512:30 p.m.YWG - ORD
2 stops11h 22mDelta
Sun 12/58:45 a.m.ORD - YWG
2 stops14h 38mDelta
Deal found 17/4C$ 606
Fri 3/57:00 a.m.YWG - ORD
1 stop7h 55mDelta
Sun 12/57:00 a.m.ORD - YWG
2 stops16h 23mDelta
Deal found 16/4C$ 609
Wed 24/47:30 a.m.YWG - MDW
1 stop7h 09mMultiple Airlines
Mon 29/410:59 p.m.MDW - YWG
2 stops21h 02mMultiple Airlines
Deal found 17/4C$ 625
Wed 24/47:30 a.m.YWG - ORD
1 stop13h 35mMultiple Airlines
Mon 29/410:00 p.m.ORD - YWG
3 stops21h 48mMultiple Airlines
Deal found 15/4C$ 632
Wed 24/47:30 a.m.YWG - MDW
1 stop7h 09mMultiple Airlines
Mon 29/411:05 a.m.MDW - YWG
1 stop10h 07mMultiple Airlines
Deal found 15/4C$ 639
Wed 24/47:30 a.m.YWG - ORD
2 stops16h 39mMultiple Airlines
Mon 29/410:00 p.m.ORD - YWG
3 stops21h 48mMultiple Airlines
Deal found 15/4C$ 646
Sat 25/58:30 a.m.YWG - ORD
1 stop8h 35mWestJet
Sun 26/55:40 a.m.ORD - YWG
1 stop9h 45mWestJet
Deal found 17/4C$ 647
Mon 27/52:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sat 1/66:00 a.m.ORD - YWG
1 stop10h 00mAir Canada
Deal found 17/4C$ 651

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 506,061 searches. Data last updated 18 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 24/47:30 a.m.YWG - ORD
1 stop9h 57mMultiple Airlines
Mon 29/48:05 p.m.ORD - YWG
2 stops23h 43mMultiple Airlines
Deal found 15/4C$ 542
Mon 17/68:30 a.m.YWG - ORD
1 stop8h 27mDelta
Tue 25/67:05 a.m.ORD - YWG
2 stops16h 24mDelta
Deal found 17/4C$ 570
Fri 3/512:30 p.m.YWG - ORD
2 stops11h 22mDelta
Sun 12/58:45 a.m.ORD - YWG
2 stops14h 38mDelta
Deal found 17/4C$ 606
Fri 3/57:00 a.m.YWG - ORD
1 stop7h 55mDelta
Sun 12/57:00 a.m.ORD - YWG
2 stops16h 23mDelta
Deal found 16/4C$ 609
Fri 13/125:38 p.m.YWG - ORD
2 stops14h 44mDelta
Sun 15/129:30 a.m.ORD - YWG
1 stop7h 17mDelta
Deal found 17/4C$ 620
Wed 24/47:30 a.m.YWG - MDW
1 stop7h 09mMultiple Airlines
Mon 29/410:59 p.m.MDW - YWG
2 stops21h 02mMultiple Airlines
Deal found 17/4C$ 625
Tue 4/65:00 a.m.YWG - ORD
1 stop7h 54mUnited Airlines
Sat 8/64:00 p.m.ORD - YWG
1 stop8h 10mUnited Airlines
Deal found 17/4C$ 631
Wed 24/47:30 a.m.YWG - ORD
1 stop13h 35mMultiple Airlines
Mon 29/410:00 p.m.ORD - YWG
3 stops21h 48mMultiple Airlines
Deal found 15/4C$ 632
Fri 27/98:30 a.m.YWG - ORD
1 stop8h 39mDelta
Tue 1/101:35 p.m.ORD - YWG
2 stops9h 46mDelta
Deal found 17/4C$ 635

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 506,061 searches. Data last updated 18 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 28mAir Canada
Sun 26/51:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 17/4C$ 756
Mon 27/52:18 p.m.YWG - ORD
Nonstop2h 28mWestJet Encore
Sat 1/61:03 p.m.ORD - YWG
Nonstop2h 26mWestJet Encore
Deal found 17/4C$ 894
Mon 27/52:18 p.m.YWG - ORD
Nonstop2h 28mWestJet Encore
Sat 1/61:03 p.m.ORD - YWG
Nonstop2h 26mWestJet Encore
Deal found 16/4C$ 927
Sat 28/92:15 p.m.YWG - ORD
Nonstop2h 21mUnited Airlines
Tue 1/101:00 p.m.ORD - YWG
Nonstop2h 24mUnited Airlines
Deal found 17/4C$ 1,009
Wed 18/92:24 p.m.YWG - ORD
Nonstop2h 32mAir Canada
Tue 24/91:05 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 16/4C$ 1,038
Thu 30/52:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Sun 2/61:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 16/4C$ 1,041
Thu 30/52:18 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Sun 2/61:03 p.m.ORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 17/4C$ 1,042
Fri 27/92:15 p.m.YWG - ORD
Nonstop2h 21mAir Canada
Tue 1/101:00 p.m.ORD - YWG
Nonstop2h 24mAir Canada
Deal found 17/4C$ 1,071
Fri 7/62:18 p.m.YWG - ORD
Nonstop2h 28mAir Canada
Fri 14/61:03 p.m.ORD - YWG
Nonstop2h 26mAir Canada
Deal found 16/4C$ 1,116

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 506,061 searches. Data last updated 18 April 2024.
Book one of these great deals on flights from Winnipeg to Chicago. Tip: verify your flight details before completing your reservation.
Wed 24/47:30 a.m.YWG - ORD
1 stop9h 57mMultiple Airlines
Mon 29/48:05 p.m.ORD - YWG
2 stops23h 43mMultiple Airlines
Deal found 15/4C$ 542
Wed 24/47:30 a.m.YWG - MDW
1 stop7h 09mMultiple Airlines
Mon 29/410:59 p.m.MDW - YWG
2 stops21h 02mMultiple Airlines
Deal found 17/4C$ 625
Wed 24/47:30 a.m.YWG - ORD
1 stop13h 35mMultiple Airlines
Mon 29/410:00 p.m.ORD - YWG
3 stops21h 48mMultiple Airlines
Deal found 15/4C$ 632
Wed 24/47:30 a.m.YWG - MDW
1 stop7h 09mMultiple Airlines
Mon 29/411:05 a.m.MDW - YWG
1 stop10h 07mMultiple Airlines
Deal found 15/4C$ 639
Wed 24/47:30 a.m.YWG - ORD
2 stops16h 39mMultiple Airlines
Mon 29/410:00 p.m.ORD - YWG
3 stops21h 48mMultiple Airlines
Deal found 15/4C$ 646
Wed 24/47:30 a.m.YWG - MDW
1 stop7h 09mMultiple Airlines
Mon 29/410:59 p.m.MDW - YWG
2 stops21h 02mMultiple Airlines
Deal found 15/4C$ 686
Wed 24/47:30 a.m.YWG - ORD
3 stops25h 04mMultiple Airlines
Mon 29/410:00 p.m.ORD - YWG
3 stops21h 48mMultiple Airlines
Deal found 15/4C$ 700
Wed 24/47:30 a.m.YWG - ORD
1 stop9h 57mMultiple Airlines
Mon 29/46:00 a.m.ORD - YWG
1 stop9h 25mMultiple Airlines
Deal found 15/4C$ 752
Wed 24/47:00 a.m.YWG - MDW
2 stops9h 24mDelta
Mon 29/49:30 a.m.MDW - YWG
2 stops11h 42mDelta
Deal found 15/4C$ 1,023

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 506,061 searches. Data last updated 18 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.
Sun 14/78:00 a.m.YWG - ORD
1 stop10h 49mDelta
Deal found 17/4C$ 357
Sun 14/77:30 a.m.YWG - ORD
2 stops11h 04mDelta
Deal found 17/4C$ 366
Sun 14/77:50 p.m.YWG - MDW
2 stops25h 51mWestJet
Deal found 16/4C$ 435
Sun 14/78:00 a.m.YWG - MDW
1 stop13h 41mWestJet
Deal found 17/4C$ 491
Sun 14/78:00 a.m.YWG - MDW
1 stop13h 41mWestJet
Deal found 16/4C$ 493
Sun 28/48:00 a.m.YWG - MDW
1 stop6h 53mWestJet
Deal found 16/4C$ 603
Sun 28/47:30 a.m.YWG - MDW
2 stops8h 54mWestJet
Deal found 16/4C$ 618
Sun 14/72:25 p.m.YWG - ORD
Nonstop2h 28mUnited Airlines
Deal found 17/4C$ 969

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 506,061 searches. Data last updated 18 April 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 570 - C$ 894

Route

Depart

Return

Price

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 17/6

1 stop8h 27m

Chicago O'Hare Intl

Tue 25/6

2 stops16h 24m

C$ 570

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 5/6

2 stops9h 38m

Chicago O'Hare Intl

Fri 7/6

2 stops14h 59m

C$ 606

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Tue 4/6

1 stop7h 54m

Chicago O'Hare Intl

Sat 8/6

1 stop8h 10m

C$ 631

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 25/5

1 stop8h 35m

Chicago O'Hare Intl

Sun 26/5

2 stops12h 51m

C$ 646

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 25/5

1 stop8h 35m

Chicago O'Hare Intl

Sun 26/5

1 stop9h 45m

C$ 647

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 27/5

Nonstop2h 28m

Chicago O'Hare Intl

Sat 1/6

1 stop10h 00m

C$ 651

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 25/5

Nonstop2h 28m

Chicago O'Hare Intl

Sun 26/5

1 stop17h 06m

C$ 657

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Fri 3/5

1 stop6h 39m

Chicago Midway

Sun 12/5

1 stop8h 40m

C$ 740

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 27/5

Nonstop2h 28m

Chicago O'Hare Intl

Sat 1/6

Nonstop2h 26m

C$ 894

Flights are sorted by cheapest first

Deals found on 17/4

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.
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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 14 April 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Winnipeg to Chicago flight should consider departing on Friday evenings 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$ 541 while a round-trip flight costs C$ 671. Price data was last updated on 14 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$ 360

February

C$ 420

March

C$ 447

April

C$ 472

May

C$ 537

June

C$ 530

July

C$ 606

August

C$ 624

September

C$ 475

October

C$ 511

November

C$ 466

December

C$ 482

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 April 2024.
Get a feel of what it's like to fly with Delta, Air Canada and United Airlines 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
11,104 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.5

Overall

8.1

Entertainment

8.0

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

Delta
8.1
Very good
11,104 reviews
Delta
8.1
Very good
11,104 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.5

Overall

8.1

Entertainment

8.0

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

WestJet
7.5
Good
3,010 reviews
Delta
8.1
Very good
11,104 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.5

Overall

8.1

Entertainment

8.0

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

United Airlines
7.4
Good
11,346 reviews
Delta
8.1
Very good
11,104 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.5

Overall

8.1

Entertainment

8.0

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

Air Canada
7.0
Good
6,832 reviews
Delta
8.1
Very good
11,104 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.5

Overall

8.1

Entertainment

8.0

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

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$ 600 on Cheapflights?

    Yes, there are multiple flights from Winnipeg to Chicago for under C$ 600. The cheapest flight booked recently is on Delta for just C$ 570, but on average you can expect to pay C$ 660.

  • 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$ 1,297.

  • Are there last-minute flights available from Winnipeg to Chicago for under C$ 600?

    There are currently 14+ open flights from Winnipeg to Chicago within the next 7 days for less than C$ 600.

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

    Delta, at C$ 570, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include United Airlines and WestJet. Delta is priced at 22% 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 Delta, with whom users have recently found tickets for as low as C$ 357. However, be on the lookout for offers from WestJet 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$ 269. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 570 on average our data indicates C$ 856 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 17/4.

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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 506,061 searches. Data last updated 18 April 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 383AverageC$ 657FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Endeavor AirlinesCheapestC$ 466AverageC$ 831FlexibilityNo cancel feeOn-timeN/A
Search Endeavor Airlines flights
DeltaCheapestC$ 489AverageC$ 683FlexibilityNo cancel feeOn-timeN/A
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WestJetCheapestC$ 550AverageC$ 802FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 599AverageC$ 761FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJet EncoreCheapestC$ 791AverageC$ 809FlexibilityNo 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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