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Cheap flights from Winnipeg (YWG) to Chicago (CHI) from $174

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 6/7. 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
May 6 — May 131
From?
To?
Mon 5/6
Mon 5/13
1 adult, Economy
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The best prices from Winnipeg to Chicago are usually found in April or January, booked 23 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 May 1, 2024.

Popular in

March

Cheapest in

April

Average price

$482

Round-trip from

$223
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 May 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?

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

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 $594.

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

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, April can be a great choice for travel to Chicago. Flights to Chicago from Winnipeg in April are about $532 on average during April, but can be found for as low as $344.

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

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 12% on your trip compared to booking a flight in the morning.

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 2,913,887 searches. Data last updated May 1, 2024.
Peruse some of the lowest-priced WestJet flights we've found from Winnipeg to Chicago. Make sure to check back often as deals are often changing.
Fri 5/248:30 amYWG - ORD
1 stop8h 35mWestJet
Tue 5/289:36 amORD - YWG
2 stops13h 04mWestJet
Deal found 4/30$362
Sat 5/258:30 amYWG - ORD
1 stop8h 35mWestJet
Fri 5/317:00 amORD - YWG
1 stop8h 25mWestJet
Deal found 4/28$376
Sat 5/258:30 amYWG - ORD
1 stop8h 35mWestJet
Wed 5/295:40 amORD - YWG
1 stop9h 45mWestJet
Deal found 4/29$377
Sat 6/156:55 amYWG - ORD
1 stop10h 02mWestJet
Mon 6/178:35 pmORD - YWG
1 stop26h 54mWestJet
Deal found 4/30$378
Sat 5/258:30 amYWG - ORD
1 stop8h 35mWestJet
Wed 5/299:36 amORD - YWG
2 stops14h 21mWestJet
Deal found 4/28$382
Sat 6/159:35 amYWG - ORD
2 stops11h 28mWestJet
Mon 6/178:35 pmORD - YWG
1 stop26h 54mWestJet
Deal found 4/30$385
Mon 5/276:55 amYWG - ORD
1 stop9h 54mWestJet
Sat 6/16:07 amORD - YWG
2 stops16h 33mWestJet
Deal found 4/29$386
Sat 5/257:30 amYWG - ORD
2 stops13h 25mWestJet
Fri 5/317:00 amORD - YWG
1 stop8h 25mWestJet
Deal found 4/28$392
Sat 6/157:30 amYWG - ORD
2 stops9h 18mWestJet
Tue 6/183:55 pmORD - YWG
1 stop7h 34mWestJet
Deal found 4/30$403

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 2,913,887 searches. Data last updated May 1, 2024.
To aid your search, here are some of the cheapest Delta flights we've found from Winnipeg to Chicago. Check back soon if you're not seeing flights that suit your needs.
Sat 6/156:55 amYWG - ORD
2 stops14h 08mDelta
Mon 6/173:55 pmORD - YWG
1 stop7h 34mDelta
Deal found 4/30$295
Tue 6/256:55 amYWG - MDW
2 stops10h 09mDelta
Sun 6/307:11 pmMDW - YWG
1 stop4h 18mDelta
Deal found 4/30$316
Sun 6/166:55 amYWG - MDW
1 stop6h 49mDelta
Tue 6/182:24 pmMDW - YWG
1 stop9h 05mDelta
Deal found 4/30$318
Wed 5/296:55 amYWG - MDW
2 stops10h 11mDelta
Wed 6/57:10 pmMDW - YWG
1 stop4h 13mDelta
Deal found 4/29$340
Sun 6/166:55 amYWG - ORD
2 stops9h 54mDelta
Tue 6/183:55 pmORD - YWG
1 stop7h 34mDelta
Deal found 4/30$356
Tue 6/256:55 amYWG - MDW
1 stop6h 49mDelta
Mon 7/17:11 pmMDW - YWG
1 stop4h 18mDelta
Deal found 4/30$358
Tue 6/256:55 amYWG - MDW
1 stop6h 49mDelta
Mon 7/17:11 pmMDW - YWG
1 stop4h 18mDelta
Deal found 4/30$360
Sat 5/256:55 amYWG - MDW
1 stop4h 07mDelta
Wed 5/299:32 amMDW - YWG
2 stops11h 40mDelta
Deal found 4/30$368
Tue 6/256:55 amYWG - MDW
1 stop6h 49mDelta
Tue 7/212:08 pmMDW - YWG
1 stop11h 21mDelta
Deal found 4/30$387

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 2,913,887 searches. Prices were last updated on May 1, 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back regularly for other flight deals.
Wed 5/88:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Wed 5/156:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Deal found 4/29$292
Wed 5/88:00 amYWG - ORD
1 stop12h 35mMultiple Airlines
Wed 5/156:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Deal found 4/29$308
Wed 5/88:00 amYWG - ORD
1 stop12h 35mMultiple Airlines
Wed 5/1510:58 amORD - YWG
3 stops28h 27mMultiple Airlines
Deal found 4/29$312
Wed 5/88:00 amYWG - ORD
2 stops24h 55mMultiple Airlines
Wed 5/1510:58 amORD - YWG
3 stops28h 27mMultiple Airlines
Deal found 4/29$326
Wed 5/296:55 amYWG - MDW
2 stops10h 11mDelta
Wed 6/57:10 pmMDW - YWG
1 stop4h 13mDelta
Deal found 4/29$340
Fri 5/248:30 amYWG - ORD
1 stop8h 35mWestJet
Tue 5/289:36 amORD - YWG
2 stops13h 04mWestJet
Deal found 4/30$362
Wed 5/298:00 amYWG - ORD
2 stops24h 55mMultiple Airlines
Wed 6/511:01 amORD - YWG
3 stops28h 24mMultiple Airlines
Deal found 4/29$364
Wed 5/298:00 amYWG - ORD
1 stop12h 35mMultiple Airlines
Wed 6/56:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Deal found 4/29$365
Fri 5/244:00 pmYWG - ORD
2 stops24h 35mMultiple Airlines
Tue 5/286:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Deal found 4/30$375

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 2,913,887 searches. Data last updated May 1, 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back regularly for other flight deals.
Wed 5/88:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Wed 5/156:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Deal found 4/29$292
Fri 6/146:55 amYWG - MDW
1 stop6h 49mDelta
Tue 6/182:24 pmMDW - YWG
1 stop9h 05mDelta
Deal found 4/30$295
Sat 6/156:55 amYWG - ORD
2 stops14h 08mDelta
Mon 6/173:55 pmORD - YWG
1 stop7h 34mDelta
Deal found 4/30$295
Wed 5/88:00 amYWG - ORD
1 stop12h 35mMultiple Airlines
Wed 5/156:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Deal found 4/29$308
Wed 5/88:00 amYWG - ORD
1 stop12h 35mMultiple Airlines
Wed 5/1510:58 amORD - YWG
3 stops28h 27mMultiple Airlines
Deal found 4/29$312
Sun 6/166:55 amYWG - MDW
1 stop6h 49mDelta
Tue 6/182:24 pmMDW - YWG
1 stop9h 05mDelta
Deal found 4/30$318
Wed 5/88:00 amYWG - ORD
2 stops24h 55mMultiple Airlines
Wed 5/1510:58 amORD - YWG
3 stops28h 27mMultiple Airlines
Deal found 4/29$326
Wed 5/296:55 amYWG - MDW
1 stop6h 40mDelta
Wed 6/57:10 pmMDW - YWG
1 stop4h 13mDelta
Deal found 4/29$340
Sat 6/156:55 amYWG - MDW
1 stop4h 32mDelta
Tue 6/182:24 pmMDW - YWG
1 stop9h 05mDelta
Deal found 4/30$356

Non-stop 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 2,913,887 searches. Data last updated May 1, 2024.
To help reduce your travel time, choose from one of these non-stop flights from Winnipeg to Chicago. Search for alternative flights from Winnipeg to Chicago by utilizing the search form above.
Tue 5/282:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Thu 5/301:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 4/28$434
Fri 5/242:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Thu 5/301:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 4/28$495
Sat 5/252:18 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Wed 5/291:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 4/29$496
Sat 5/252:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Wed 5/291:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 4/28$518
Fri 5/242:18 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Tue 5/281:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 4/30$538
Wed 5/292:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Wed 6/51:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 4/29$616
Wed 9/182:24 pmYWG - ORD
Nonstop2h 32mUnited Airlines
Tue 9/241:05 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 4/30$646
Mon 5/272:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Sat 6/11:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 4/29$676
Mon 5/272:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Sat 6/11:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 4/30$677

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 2,913,887 searches. Data last updated May 1, 2024.
Have a look at some of the flights available from Winnipeg to Chicago departing last-minute. It's wise to confirm all flight details are correct before booking.
Wed 5/88:00 amYWG - ORD
1 stop9h 27mMultiple Airlines
Wed 5/156:00 amORD - YWG
1 stop9h 25mMultiple Airlines
Deal found 4/29$292
Wed 5/88:00 amYWG - ORD
1 stop12h 35mMultiple Airlines
Wed 5/156:40 pmORD - YWG
2 stops20h 45mMultiple Airlines
Deal found 4/29$308
Wed 5/88:00 amYWG - ORD
1 stop12h 35mMultiple Airlines
Wed 5/1510:58 amORD - YWG
3 stops28h 27mMultiple Airlines
Deal found 4/29$312
Wed 5/88:00 amYWG - ORD
2 stops24h 55mMultiple Airlines
Wed 5/1510:58 amORD - YWG
3 stops28h 27mMultiple Airlines
Deal found 4/29$326
Tue 5/712:22 pmYWG - ORD
1 stop4h 27mMultiple Airlines
Thu 5/167:00 amORD - YWG
1 stop8h 25mMultiple Airlines
Deal found 4/29$391
Wed 5/88:00 amYWG - ORD
3 stops27h 08mMultiple Airlines
Wed 5/1510:58 amORD - YWG
3 stops28h 27mMultiple Airlines
Deal found 4/29$408
Tue 5/77:30 amYWG - ORD
2 stops12h 05mWestJet
Thu 5/168:45 pmORD - YWG
1 stop18h 40mWestJet
Deal found 4/29$425
Tue 5/76:30 amYWG - ORD
2 stops10h 19mWestJet
Thu 5/1611:45 amORD - YWG
2 stops9h 27mWestJet
Deal found 4/29$430
Tue 5/74:00 pmYWG - ORD
2 stops25h 40mMultiple Airlines
Thu 5/162:56 pmORD - YWG
3 stops33h 48mMultiple Airlines
Deal found 4/29$440

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 2,913,887 searches. Data last updated May 1, 2024.
Take a look at some of the best available options we've come across on one-way flights from Winnipeg to Chicago. Users in need of a round-trip flight from Winnipeg to Chicago instead should update the search form at the top of page.
Fri 6/712:26 pmYWG - ORD
2 stops11h 30mDelta
Deal found 4/30$174
Thu 6/67:30 amYWG - ORD
1 stop7h 24mAir Canada
Deal found 4/30$179
Mon 8/268:00 amYWG - ORD
1 stop12h 35mMultiple Airlines
Deal found 4/29$193
Fri 6/75:00 pmYWG - ORD
1 stop8h 59mMultiple Airlines
Deal found 4/30$198
Fri 6/76:30 amYWG - MDW
2 stops12h 06mWestJet
Deal found 4/30$204
Fri 6/712:26 pmYWG - MDW
1 stop6h 10mWestJet
Deal found 4/30$209
Thu 6/68:00 amYWG - ORD
2 stops16h 55mMultiple Airlines
Deal found 4/30$219
Mon 8/266:30 amYWG - ORD
2 stops11h 12mMultiple Airlines
Deal found 4/29$220
Thu 6/68:00 amYWG - MDW
1 stop14h 01mWestJet
Deal found 4/30$221

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 2,913,887 searches. Data last updated May 1, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$295 - $742

Route

Depart

Return

Price

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Fri 6/14

1 stop6h 49m

Chicago Midway

Tue 6/18

1 stop9h 05m

$295

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 6/15

2 stops14h 08m

Chicago O'Hare Intl

Mon 6/17

1 stop7h 34m

$295

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Tue 6/25

2 stops10h 09m

Chicago Midway

Sun 6/30

1 stop4h 18m

$316

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Mon 6/3

1 stop6h 41m

Chicago Midway

Sun 6/16

1 stop8h 26m

$342

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Fri 5/24

1 stop8h 35m

Chicago O'Hare Intl

Tue 5/28

2 stops13h 04m

$362

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 5/29

2 stops24h 55m

Chicago O'Hare Intl

Wed 6/5

3 stops28h 24m

$364

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Tue 6/4

1 stop6h 21m

Chicago O'Hare Intl

Sat 6/8

1 stop11h 40m

$380

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 5/25

Nonstop2h 28m

Chicago O'Hare Intl

Wed 5/29

1 stop15h 40m

$407

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Wed 6/26

2 stops9h 47m

Chicago Midway

Mon 7/1

2 stops9h 52m

$742

Flights are sorted by cheapest first

Deals found on 4/30

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 January 28, 2024.
The price you pay for your flight from Winnipeg to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 23 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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When is the cheapest time to fly from 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 April 28, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Winnipeg to Chicago flight should consider departing on Thursday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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Average price of flights to 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 $202 while a round-trip flight costs $389. Price data was last updated on April 28, 2024.

Currently, February is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in June is currently the most expensive (average of $354). 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

$248

February

$245

March

$280

April

$267

May

$279

June

$354

July

$334

August

$274

September

$258

October

$248

November

$270

December

$248

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

23 - 73.4 °F

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 May 1, 2024.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as WestJet, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,895 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Boarding

8.2

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
8.1
Very good
10,895 reviews
Delta
8.1
Very good
10,895 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Boarding

8.2

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
7.6
Good
2,970 reviews
Delta
8.1
Very good
10,895 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Boarding

8.2

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
436 reviews
Delta
8.1
Very good
10,895 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Boarding

8.2

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
11,187 reviews
Delta
8.1
Very good
10,895 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Boarding

8.2

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.

Air Canada
7.0
Good
6,889 reviews
Delta
8.1
Very good
10,895 reviews
Check prices

Entertainment

8.0

Comfort

7.9

Food

7.4

Overall

8.1

Crew

8.6

Boarding

8.2

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?

    Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Chicago. On average, Winnipeg has 0 outbound flights to Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • Can I find flights from Winnipeg to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Winnipeg to Chicago for under $300. The cheapest flight booked recently is on Delta for just $295, but on average you can expect to pay $353.

  • Are there nonstop flights from Winnipeg to Chicago for under $500 on Cheapflights?

    Cheapflights has at least 20 direct flights from Winnipeg to Chicago under $500. A good price for a nonstop flight from Winnipeg to Chicago is less than $697.

  • Are there last-minute flights available from Winnipeg to Chicago for under $300?

    There are currently 9+ open flights from Winnipeg to Chicago within the next 7 days for less than $300.

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

    Our cheapest airline available from Winnipeg to Chicago is Delta. Our recent data shows that you can find tickets from as low as $295 on this airline. Additional options worth looking into are WestJet and Air Canada, starting at $362 and $380 round-trip. Users have found that Delta is 44% cheaper than the other options available to this destination.

  • 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 $174. However, be on the lookout for offers from Air Canada and WestJet, as they are both options that can get you from Winnipeg to Chicago for a low price.

  • What are the cheapest flights from Winnipeg to Chicago?

    While on average a flight from Winnipeg to Chicago is generally $599, our data shows the cheapest flight currently is $309. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $292 for that flight.

  • What does YWG to ORD mean?

    YWG stands for Winnipeg Airport, while ORD stands for Chicago O'Hare Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: 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 4/30.

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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.

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Top 2 airlines flying from Winnipeg to Chicago

Discover the top 2 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 2,913,887 searches. Data last updated May 1, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$284Average$470FlexibilityNo cancel feeOn-time67%
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DeltaCheapest$391Average$554FlexibilityNo cancel feeOn-timeN/A
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When you search for this flight from Winnipeg to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Chicago for you. Better yet — we are completely free to use.

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Users can book flights with no change fees policies with our dedicated filters. Book flights from Winnipeg to Chicago flexibly with Cheapflights today.

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Yes! Start tracking prices for Winnipeg to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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