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Cheap flights from Winnipeg (YWG) to Chicago (CHI) from $157

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 8/2. 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
Jun 1 — Jun 81
From?
To?
Sat 6/1
Sat 6/8
1 adult, Economy
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The best prices from Winnipeg to Chicago are usually found in November or March, booked 16 days in advance, depart on a Tuesday or Thursday 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 27, 2024.

Popular in

August

Cheapest in

November

Average price

$463

Round-trip from

$223
High demand for flights, 14% potential price rise
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Best time to find cheap flights, 12% 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 Friday. 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 80% 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 $522.

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

Due to multiple factors, expect to potentially pay more when booking in August. For low rates, November can be a great choice for travel to Chicago. Flights to Chicago from Winnipeg in November are about $514 on average during November, but can be found for as low as $272.

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 at noon. If you’re flexible enough to do this you can expect to save up to 8% 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 2,671,228 searches. Data last updated May 27, 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.
Mon 8/58:30 amYWG - ORD
1 stop8h 27mWestJet
Sat 8/105:55 pmORD - YWG
1 stop17h 43mWestJet
Deal found 5/26$313
Sat 6/226:55 amYWG - ORD
1 stop8h 10mWestJet
Mon 6/248:35 pmORD - YWG
1 stop15h 00mWestJet
Deal found 5/25$355
Sat 6/226:55 amYWG - ORD
1 stop8h 10mWestJet
Tue 6/2512:35 pmORD - YWG
1 stop23h 00mWestJet
Deal found 5/25$361
Tue 6/412:22 pmYWG - ORD
1 stop10h 19mWestJet
Sat 6/86:05 amORD - YWG
1 stop17h 24mWestJet
Deal found 5/26$362
Fri 6/216:55 amYWG - ORD
1 stop15h 02mWestJet
Tue 6/2512:35 pmORD - YWG
1 stop10h 54mWestJet
Deal found 5/25$364
Fri 6/216:55 amYWG - ORD
1 stop15h 02mWestJet
Sat 6/295:55 pmORD - YWG
1 stop26h 04mWestJet
Deal found 5/26$365
Wed 6/196:55 amYWG - ORD
1 stop15h 02mWestJet
Mon 6/248:35 pmORD - YWG
1 stop15h 00mWestJet
Deal found 5/25$366
Tue 6/117:30 amYWG - ORD
2 stops16h 26mWestJet
Fri 6/148:35 pmORD - YWG
1 stop26h 54mWestJet
Deal found 5/26$369
Wed 6/196:55 amYWG - ORD
1 stop15h 02mWestJet
Tue 6/2512:35 pmORD - YWG
2 stops11h 22mWestJet
Deal found 5/25$372

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 2,671,228 searches. Data last updated May 27, 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 6/226:55 amYWG - MDW
2 stops10h 09mDelta
Tue 6/252:24 pmMDW - YWG
1 stop9h 05mDelta
Deal found 5/25$428
Fri 7/265:28 pmYWG - MDW
2 stops15h 58mDelta
Mon 7/299:33 amMDW - YWG
2 stops13h 55mDelta
Deal found 5/26$437
Thu 7/46:55 amYWG - ORD
2 stops14h 08mDelta
Sun 7/78:30 amORD - YWG
2 stops15h 17mDelta
Deal found 5/26$443
Tue 7/236:55 amYWG - MDW
2 stops10h 09mDelta
Tue 7/302:49 pmMDW - YWG
1 stop8h 39mDelta
Deal found 5/26$457
Sun 7/216:55 amYWG - MDW
2 stops10h 09mDelta
Fri 7/262:49 pmMDW - YWG
1 stop8h 39mDelta
Deal found 5/26$474
Mon 10/77:30 amYWG - ORD
2 stops9h 01mDelta
Mon 10/148:55 amORD - YWG
2 stops14h 17mDelta
Deal found 5/25$526

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 2,671,228 searches. Prices were last updated on May 27, 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back regularly for other flight deals.
Sat 6/226:55 amYWG - ORD
1 stop8h 10mWestJet
Mon 6/248:35 pmORD - YWG
1 stop15h 00mWestJet
Deal found 5/25$355
Sat 6/226:55 amYWG - ORD
1 stop8h 10mWestJet
Tue 6/2512:35 pmORD - YWG
1 stop23h 00mWestJet
Deal found 5/25$361
Wed 5/296:55 amYWG - ORD
1 stop7h 47mWestJet
Sun 6/26:07 amORD - YWG
1 stop17h 16mWestJet
Deal found 5/26$362
Fri 6/216:55 amYWG - ORD
1 stop15h 02mWestJet
Tue 6/2512:35 pmORD - YWG
1 stop10h 54mWestJet
Deal found 5/25$364
Thu 5/308:50 pmYWG - ORD
1 stop20h 15mWestJet
Sun 6/26:07 amORD - YWG
1 stop17h 16mWestJet
Deal found 5/26$365
Wed 6/196:55 amYWG - ORD
1 stop15h 02mWestJet
Tue 6/259:20 amORD - YWG
2 stops13h 22mWestJet
Deal found 5/26$366
Tue 6/117:30 amYWG - ORD
2 stops16h 26mWestJet
Fri 6/148:35 pmORD - YWG
1 stop26h 54mWestJet
Deal found 5/26$369
Wed 6/196:55 amYWG - ORD
1 stop15h 02mWestJet
Tue 6/2512:35 pmORD - YWG
2 stops11h 22mWestJet
Deal found 5/25$372
Sat 6/226:55 amYWG - ORD
1 stop8h 10mWestJet
Sat 6/225:55 pmORD - YWG
1 stop17h 45mWestJet
Deal found 5/25$377

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 2,671,228 searches. Data last updated May 27, 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back regularly for other flight deals.
Mon 8/58:30 amYWG - ORD
1 stop8h 27mWestJet
Sat 8/105:55 pmORD - YWG
1 stop17h 43mWestJet
Deal found 5/26$313
Sat 6/226:55 amYWG - ORD
1 stop8h 10mWestJet
Mon 6/248:35 pmORD - YWG
1 stop15h 00mWestJet
Deal found 5/25$355
Sat 6/226:55 amYWG - ORD
1 stop8h 10mWestJet
Tue 6/2512:35 pmORD - YWG
1 stop23h 00mWestJet
Deal found 5/25$361
Wed 5/296:55 amYWG - ORD
1 stop7h 47mWestJet
Sun 6/26:07 amORD - YWG
1 stop17h 16mWestJet
Deal found 5/26$362
Fri 6/216:55 amYWG - ORD
1 stop15h 02mWestJet
Tue 6/2512:35 pmORD - YWG
1 stop10h 54mWestJet
Deal found 5/25$364
Thu 5/308:50 pmYWG - ORD
1 stop20h 15mWestJet
Sun 6/26:07 amORD - YWG
1 stop17h 16mWestJet
Deal found 5/26$365
Wed 6/196:55 amYWG - ORD
1 stop15h 02mWestJet
Tue 6/259:20 amORD - YWG
2 stops13h 22mWestJet
Deal found 5/26$366
Tue 6/117:30 amYWG - ORD
2 stops16h 26mWestJet
Fri 6/148:35 pmORD - YWG
1 stop26h 54mWestJet
Deal found 5/26$369
Wed 6/196:55 amYWG - ORD
1 stop15h 02mWestJet
Tue 6/2512:35 pmORD - YWG
2 stops11h 22mWestJet
Deal found 5/25$372

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 2,671,228 searches. Data last updated May 27, 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.
Wed 6/192:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Fri 6/211:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/25$499
Thu 6/202:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Fri 6/211:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/25$530
Wed 9/182:24 pmYWG - ORD
Nonstop2h 32mAir Canada
Tue 9/241:05 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/26$541
Sun 6/162:18 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Sun 6/231:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 5/26$559
Wed 6/192:18 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Tue 6/251:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 5/26$562
Thu 7/42:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Sun 7/71:15 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 5/26$576
Thu 6/202:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Sun 6/231:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/25$606
Wed 6/192:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Thu 6/271:15 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/25$614
Thu 6/132:18 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Wed 6/191:03 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 5/26$633

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 2,671,228 searches. Data last updated May 27, 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.
Tue 6/412:22 pmYWG - ORD
1 stop10h 19mWestJet
Sat 6/86:05 amORD - YWG
1 stop17h 24mWestJet
Deal found 5/26$362
Tue 6/46:30 amYWG - ORD
2 stops16h 11mWestJet
Sat 6/86:05 amORD - YWG
1 stop17h 24mWestJet
Deal found 5/26$366
Tue 6/412:22 pmYWG - MDW
1 stop5h 45mWestJet
Sat 6/812:07 pmMDW - YWG
1 stop23h 28mWestJet
Deal found 5/26$402
Tue 6/46:30 amYWG - MDW
2 stops11h 37mWestJet
Sat 6/812:07 pmMDW - YWG
1 stop11h 22mWestJet
Deal found 5/26$416
Tue 6/46:30 amYWG - ORD
2 stops16h 11mWestJet
Sat 6/86:00 amORD - YWG
2 stops15h 12mWestJet
Deal found 5/26$436
Tue 6/46:30 amYWG - MDW
2 stops11h 37mWestJet
Sat 6/86:00 amMDW - YWG
2 stops15h 12mWestJet
Deal found 5/26$460
Tue 6/45:10 amYWG - ORD
1 stop7h 49mAir Canada
Sat 6/81:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/26$784
Tue 6/42:18 pmYWG - ORD
Nonstop2h 28mAir Canada
Sat 6/81:03 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/26$1,067

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 2,671,228 searches. Data last updated May 27, 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 8/28:30 amYWG - ORD
1 stop8h 27mWestJet
Deal found 5/26$157
Thu 10/178:00 amYWG - MDW
1 stop12h 49mMultiple Airlines
Deal found 5/26$220
Thu 10/178:00 amYWG - ORD
1 stop10h 34mMultiple Airlines
Deal found 5/26$220
Fri 8/27:50 pmYWG - MDW
2 stops13h 36mWestJet
Deal found 5/26$255
Sun 7/146:55 amYWG - MDW
1 stop11h 44mWestJet
Deal found 5/27$262
Sun 7/148:00 amYWG - ORD
1 stop10h 46mWestJet
Deal found 5/26$262
Sat 8/37:30 amYWG - ORD
1 stop7h 24mAir Canada
Deal found 5/26$264
Fri 8/28:15 pmYWG - ORD
2 stops12h 47mWestJet
Deal found 5/26$265
Fri 8/28:00 amYWG - MDW
1 stop10h 05mWestJet
Deal found 5/26$269

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 2,671,228 searches. Data last updated May 27, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$313 - $470

Route

Depart

Return

Price

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 8/5

1 stop8h 27m

Chicago O'Hare Intl

Sat 8/10

1 stop17h 43m

$313

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 6/22

1 stop8h 10m

Chicago O'Hare Intl

Mon 6/24

1 stop15h 00m

$355

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 6/22

1 stop8h 10m

Chicago O'Hare Intl

Tue 6/25

1 stop23h 00m

$361

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Tue 7/23

2 stops14h 47m

Chicago O'Hare Intl

Tue 7/30

2 stops20h 39m

$380

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 8/5

2 stops11h 56m

Chicago O'Hare Intl

Fri 8/9

1 stop29h 17m

$386

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Tue 6/25

1 stop7h 41m

Chicago O'Hare Intl

Wed 6/26

1 stop8h 47m

$417

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Sat 6/22

2 stops10h 09m

Chicago Midway

Tue 6/25

1 stop9h 05m

$428

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 6/20

Nonstop2h 28m

Chicago O'Hare Intl

Tue 6/25

1 stop5h 52m

$458

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

Thu 6/13

2 stops9h 47m

Chicago Midway

Wed 6/19

1 stop11h 15m

$470

Flights are sorted by cheapest first

Deals found on 5/26

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 May 24, 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 16 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 May 26, 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. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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Best time to book a flight from Winnipeg to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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 27, 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
8.0
Very good
10,512 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

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
8.0
Very good
10,512 reviews
Delta
8.0
Very good
10,512 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

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
7.5
Good
2,890 reviews
Delta
8.0
Very good
10,512 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

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
10,810 reviews
Delta
8.0
Very good
10,512 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

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
7.3
Good
398 reviews
Delta
8.0
Very good
10,512 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

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
6,983 reviews
Delta
8.0
Very good
10,512 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

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 $400 on Cheapflights?

    Yes, there are multiple flights from Winnipeg to Chicago for under $400. The cheapest flight booked recently is on WestJet for just $313, but on average you can expect to pay $380.

  • 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 $646.

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

    There are currently 8+ open flights from Winnipeg to Chicago within the next 7 days for less than $400.

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

    Our cheapest airline available from Winnipeg to Chicago is WestJet. Our recent data shows that you can find tickets from as low as $313 on this airline. An additional option worth looking into is United Airlines, starting at $417. Users have found that WestJet is 39% 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 WestJet, with whom users have recently found tickets for as low as $157. 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 cheapest flights from Winnipeg to Chicago?

    While on average a flight from Winnipeg to Chicago is generally $568, our data shows the cheapest flight currently is $348. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay $265 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 5/26.

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

    Currently, February is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $244). Flying from Winnipeg to Chicago in June is currently the most expensive (average of $330). 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.

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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
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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 2,671,228 searches. Data last updated May 27, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$284Average$470FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapest$390Average$545FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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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.

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

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.

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

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

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

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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