HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Winnipeg (YWG) to Chicago (CHI) from $169

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. 4 — jun. 111
From?
To?
mar. 6/4
mar. 6/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 mayo 30, 2024.

Popular in

August

Cheapest in

November

Round-trip from

$222

One-way from

$214
High demand for flights, 14% potential price rise
Search Deals
Best time to find cheap flights, 12% potential price drop
Search Deals
From Winnipeg to Chicago (CHI)
Search Deals
One-way flight from Winnipeg to Chicago (CHI)
Search Deals

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.

What is the cheapest time of day to fly from YWG to 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 2,784,634 searches. Data last updated mayo 30, 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.
sáb. 8/318:30 amYWG - ORD
1 stop8h 27mWestJet
vie. 9/65:55 pmORD - YWG
1 stop17h 43mWestJet
Deal found 5/29$304
vie. 6/148:30 amYWG - ORD
1 stop8h 35mWestJet
dom. 6/167:10 amORD - YWG
2 stops14h 02mWestJet
Deal found 5/29$344
dom. 6/165:28 pmYWG - ORD
1 stop4h 29mWestJet
sáb. 6/225:55 pmORD - YWG
1 stop17h 45mWestJet
Deal found 5/28$346
dom. 6/169:35 amYWG - ORD
2 stops11h 23mWestJet
sáb. 6/225:55 pmORD - YWG
1 stop17h 45mWestJet
Deal found 5/28$351
dom. 6/165:28 pmYWG - ORD
1 stop4h 29mWestJet
mar. 6/187:55 pmORD - YWG
1 stop19h 27mWestJet
Deal found 5/29$362
lun. 6/108:50 pmYWG - ORD
2 stops27h 06mWestJet
mié. 6/126:05 amORD - YWG
1 stop17h 24mWestJet
Deal found 5/30$365
sáb. 6/158:15 pmYWG - ORD
2 stops13h 06mWestJet
lun. 6/178:35 pmORD - YWG
1 stop26h 54mWestJet
Deal found 5/29$367
dom. 6/169:35 amYWG - ORD
2 stops11h 23mWestJet
mar. 6/187:10 amORD - YWG
2 stops14h 02mWestJet
Deal found 5/29$372
dom. 6/169:35 amYWG - ORD
2 stops11h 23mWestJet
sáb. 6/226:00 amORD - YWG
2 stops15h 12mWestJet
Deal found 5/28$373

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 2,784,634 searches. Data last updated mayo 30, 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.
sáb. 7/206:55 amYWG - ORD
2 stops9h 37mDelta
mié. 7/247:05 amORD - YWG
2 stops16h 23mDelta
Deal found 5/29$389
sáb. 8/3112:22 pmYWG - ORD
2 stops22h 50mDelta
vie. 9/66:00 amORD - YWG
2 stops17h 28mDelta
Deal found 5/29$396
sáb. 7/206:55 amYWG - MDW
2 stops10h 09mDelta
mié. 7/249:33 amMDW - YWG
2 stops13h 55mDelta
Deal found 5/29$400
mié. 9/185:38 pmYWG - ORD
1 stop4h 09mDelta
mar. 9/241:35 pmORD - YWG
2 stops9h 46mDelta
Deal found 5/30$402
lun. 10/286:55 amYWG - ORD
1 stop8h 01mDelta
mar. 10/293:50 pmORD - YWG
1 stop7h 31mDelta
Deal found 5/29$404
sáb. 7/66:55 amYWG - ORD
1 stop8h 10mDelta
dom. 7/75:16 pmORD - YWG
1 stop6h 31mDelta
Deal found 5/29$420
vie. 7/195:28 pmYWG - MDW
2 stops15h 58mDelta
lun. 7/229:33 amMDW - YWG
2 stops13h 55mDelta
Deal found 5/29$433
dom. 9/226:55 amYWG - MDW
1 stop6h 07mDelta
vie. 9/276:45 pmMDW - YWG
1 stop4h 36mDelta
Deal found 5/29$439
lun. 8/56:55 amYWG - MDW
1 stop6h 48mDelta
sáb. 8/107:16 pmMDW - YWG
1 stop4h 15mDelta
Deal found 5/30$446

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 2,784,634 searches. Prices were last updated on mayo 30, 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back regularly for other flight deals.
mié. 6/268:00 amYWG - ORD
1 stop12h 47mMultiple Airlines
mar. 7/26:40 pmORD - YWG
2 stops20h 42mMultiple Airlines
Deal found 5/29$325
mié. 6/268:00 amYWG - ORD
2 stops26h 01mMultiple Airlines
mar. 7/26:40 pmORD - YWG
2 stops20h 42mMultiple Airlines
Deal found 5/29$340
vie. 6/148:30 amYWG - ORD
1 stop8h 35mWestJet
dom. 6/167:10 amORD - YWG
2 stops14h 02mWestJet
Deal found 5/29$344
dom. 6/165:28 pmYWG - ORD
1 stop4h 29mWestJet
sáb. 6/225:55 pmORD - YWG
1 stop17h 45mWestJet
Deal found 5/28$346
dom. 6/169:35 amYWG - ORD
2 stops11h 23mWestJet
sáb. 6/225:55 pmORD - YWG
1 stop17h 45mWestJet
Deal found 5/28$351
dom. 6/165:28 pmYWG - ORD
1 stop4h 29mWestJet
mar. 6/187:55 pmORD - YWG
1 stop19h 27mWestJet
Deal found 5/29$362
mié. 6/268:00 amYWG - ORD
1 stop12h 47mMultiple Airlines
mié. 7/35:45 pmORD - YWG
2 stops21h 37mMultiple Airlines
Deal found 5/29$364
lun. 6/108:50 pmYWG - ORD
2 stops27h 06mWestJet
mié. 6/126:05 amORD - YWG
1 stop17h 24mWestJet
Deal found 5/30$365
sáb. 6/158:15 pmYWG - ORD
2 stops13h 06mWestJet
lun. 6/178:35 pmORD - YWG
1 stop26h 54mWestJet
Deal found 5/29$367

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 2,784,634 searches. Data last updated mayo 30, 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back regularly for other flight deals.
sáb. 8/318:30 amYWG - ORD
1 stop8h 27mWestJet
vie. 9/65:55 pmORD - YWG
1 stop17h 43mWestJet
Deal found 5/29$304
mié. 6/268:00 amYWG - ORD
1 stop12h 47mMultiple Airlines
mar. 7/26:40 pmORD - YWG
2 stops20h 42mMultiple Airlines
Deal found 5/29$325
lun. 7/228:00 amYWG - ORD
1 stop12h 58mMultiple Airlines
mar. 7/309:59 pmORD - YWG
1 stop17h 23mMultiple Airlines
Deal found 5/29$326
lun. 7/226:30 amYWG - ORD
2 stops11h 49mMultiple Airlines
mar. 7/309:59 pmORD - YWG
1 stop17h 23mMultiple Airlines
Deal found 5/29$339
mié. 6/268:00 amYWG - ORD
2 stops26h 01mMultiple Airlines
mar. 7/26:40 pmORD - YWG
2 stops20h 42mMultiple Airlines
Deal found 5/29$340
vie. 6/148:30 amYWG - ORD
1 stop8h 35mWestJet
dom. 6/167:10 amORD - YWG
2 stops14h 02mWestJet
Deal found 5/29$344
dom. 6/165:28 pmYWG - ORD
1 stop4h 29mWestJet
sáb. 6/225:55 pmORD - YWG
1 stop17h 45mWestJet
Deal found 5/28$346
dom. 6/169:35 amYWG - ORD
2 stops11h 23mWestJet
sáb. 6/225:55 pmORD - YWG
1 stop17h 45mWestJet
Deal found 5/28$351
dom. 6/165:28 pmYWG - ORD
1 stop4h 29mWestJet
mar. 6/187:55 pmORD - YWG
1 stop19h 27mWestJet
Deal found 5/29$362

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 2,784,634 searches. Data last updated mayo 30, 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.
dom. 9/12:24 pmYWG - ORD
Nonstop2h 32mUnited Airlines
mié. 9/41:05 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 5/29$459
mié. 6/262:18 pmYWG - ORD
Nonstop2h 28mAir Canada
mié. 7/31:15 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/29$467
mié. 6/262:18 pmYWG - ORD
Nonstop2h 28mMultiple Airlines
mié. 7/31:15 pmORD - YWG
Nonstop2h 26mMultiple Airlines
Deal found 5/29$469
lun. 10/282:15 pmYWG - ORD
Nonstop2h 30mUnited Airlines
mar. 10/2912:52 pmORD - YWG
Nonstop2h 36mUnited Airlines
Deal found 5/29$483
vie. 6/282:25 pmYWG - ORD
Nonstop2h 28mAir Canada
mié. 7/31:15 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/29$498
jue. 6/272:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
dom. 6/301:15 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 5/30$499
sáb. 7/62:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
dom. 7/71:15 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 5/29$524
vie. 6/282:25 pmYWG - ORD
Nonstop2h 28mUnited Airlines
dom. 6/301:15 pmORD - YWG
Nonstop2h 26mUnited Airlines
Deal found 5/29$531
dom. 9/222:24 pmYWG - ORD
Nonstop2h 32mAir Canada
vie. 9/271:05 pmORD - YWG
Nonstop2h 26mAir Canada
Deal found 5/29$538

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 2,784,634 searches. Data last updated mayo 30, 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.
mar. 6/412:22 pmYWG - ORD
1 stop4h 27mWestJet
sáb. 6/84:00 pmORD - YWG
1 stop7h 29mWestJet
Deal found 5/29$412
mar. 6/46:55 amYWG - MDW
1 stop11h 12mWestJet
sáb. 6/812:07 pmMDW - YWG
1 stop11h 22mWestJet
Deal found 5/29$417
mar. 6/47:30 amYWG - ORD
2 stops12h 05mWestJet
sáb. 6/89:20 amORD - YWG
1 stop14h 09mWestJet
Deal found 5/29$417
mar. 6/46:30 amYWG - MDW
2 stops11h 37mWestJet
sáb. 6/812:07 pmMDW - YWG
1 stop11h 22mWestJet
Deal found 5/29$429
sáb. 6/87:30 amYWG - MDW
2 stops9h 34mWestJet
sáb. 6/87:11 pmMDW - YWG
1 stop4h 18mWestJet
Deal found 5/30$440
vie. 6/75:28 pmYWG - ORD
1 stop21h 37mWestJet
lun. 6/106:00 amORD - YWG
1 stop9h 25mWestJet
Deal found 5/29$449
mar. 6/49:35 amYWG - ORD
2 stops11h 20mWestJet
sáb. 6/87:10 amORD - YWG
2 stops9h 20mWestJet
Deal found 5/29$455
vie. 6/75:28 pmYWG - ORD
1 stop21h 37mWestJet
lun. 6/105:55 pmORD - YWG
2 stops27h 17mWestJet
Deal found 5/29$459
mar. 6/46:30 amYWG - MDW
2 stops11h 37mWestJet
sáb. 6/86:00 amMDW - YWG
2 stops17h 57mWestJet
Deal found 5/29$505

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 2,784,634 searches. Data last updated mayo 30, 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.
vie. 8/28:30 amYWG - ORD
1 stop8h 27mWestJet
Deal found 5/29$169
vie. 6/285:00 pmYWG - MDW
1 stop18h 01mMultiple Airlines
Deal found 5/29$180
mar. 11/197:30 amYWG - MDW
1 stop13h 19mMultiple Airlines
Deal found 5/28$188
jue. 7/118:00 amYWG - ORD
1 stop13h 39mMultiple Airlines
Deal found 5/29$190
mié. 7/318:00 amYWG - ORD
1 stop12h 58mMultiple Airlines
Deal found 5/29$192
mar. 11/197:30 amYWG - ORD
1 stop11h 04mMultiple Airlines
Deal found 5/28$193
jue. 8/16:05 pmYWG - ORD
1 stop22h 52mWestJet
Deal found 5/29$196
lun. 7/298:00 amYWG - ORD
1 stop8h 47mMultiple Airlines
Deal found 5/29$198
dom. 6/308:50 pmYWG - ORD
1 stop20h 07mWestJet
Deal found 5/29$205

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 2,784,634 searches. Data last updated mayo 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$304 - $474

Route

Depart

Return

Price

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

sáb. 8/31

1 stop8h 27m

Chicago O'Hare Intl

vie. 9/6

1 stop17h 43m

$304

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

mié. 6/26

1 stop12h 47m

Chicago O'Hare Intl

mar. 7/2

2 stops20h 42m

$325

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

lun. 7/22

1 stop12h 58m

Chicago O'Hare Intl

mar. 7/30

1 stop17h 23m

$326

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

lun. 7/22

2 stops11h 49m

Chicago O'Hare Intl

mar. 7/30

1 stop17h 23m

$339

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

vie. 6/14

1 stop8h 35m

Chicago O'Hare Intl

dom. 6/16

2 stops14h 02m

$344

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

sáb. 7/20

2 stops9h 37m

Chicago O'Hare Intl

mié. 7/24

2 stops16h 23m

$389

WinnipegChicago Midway

YWG - MDW

YWGMDW

Winnipeg

dom. 6/16

2 stops9h 47m

Chicago Midway

mar. 6/18

2 stops10h 07m

$466

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

mié. 6/26

Nonstop2h 28m

Chicago O'Hare Intl

mié. 7/3

Nonstop2h 26m

$467

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

mié. 6/26

1 stop7h 41m

Chicago O'Hare Intl

mié. 7/3

Nonstop2h 26m

$474

Flights are sorted by cheapest first

Deals found on 5/29

How far ahead should I 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.
Search Deals

What is the cheapest day 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.
Search Deals

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 mayo 30, 2024.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as WestJet, Delta and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,457 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

Crew

8.6

Overall

8.0

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
10,457 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

Crew

8.6

Overall

8.0

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
2,866 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

Crew

8.6

Overall

8.0

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
394 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

Crew

8.6

Overall

8.0

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
10,777 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

Crew

8.6

Overall

8.0

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
7,004 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Comfort

7.9

Entertainment

8.0

Food

7.4

Boarding

8.2

Crew

8.6

Overall

8.0

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 $304, but on average you can expect to pay $359.

  • 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 $555.

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

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

  • 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 $304 on this airline. An additional option worth looking into is Delta, starting at $389. Users have found that WestJet is 40% 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 $169. However, be on the lookout for offers from United Airlines 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 5/29.

  • What is the cheapest month 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 $326). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Winnipeg to Midway flights
Winnipeg to St. Louis flights

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 2,784,634 searches. Data last updated mayo 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$284Average$470FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapest$390Average$545FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Chicago to Los Angeles flights
Boston to Miami flights
Baltimore to Orlando flights
Houston to Monterrey flights
New York to Rome flights
Phoenix to Las Vegas flights
Houston to Boston flights
Ohio to Florida flights
Detroit to Boston flights
New York to Florida flights
Minneapolis to Los Angeles flights
Winnipeg to Charlotte flights

Search flights from Winnipeg to Chicago by cabin class

Find flights from Winnipeg to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Winnipeg to Chicago

Find hourly flight availability from Winnipeg to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mayo 30, 2024.
0%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
100%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Laayoune Hassan I
Flights to Virac
Flights to Figari-Sud Corse
Flights to Edremit/Korfez
Flights to Rhinelander Oneida County
Flights to Girona Costa Brava
Flights to Brainerd Crow Wing County
Flights to Parikia Paros
Flights to Cortez Montezuma County
Flights to Miyakojima Hirara
Flights to Zadar
Flights to Trapani Birgi
Flights to Provincetown
Flights to Oran Es Senia
Flights to Constanţa Mihail Kogalniceanu
Flights to Vava'u Lupepau'U
Flights to Urumqi
Flights to Hakodate
Flights to Naxos
Flights to Dalaman
Flights to Hyannis Barnstable
Flights to Devils Lake
Flights to Bastia Poretta
Flights to Karpathos

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Chicago?

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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines