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Fare Guide

Estimated lowest fares found within 7 days

The cheapest airline(s) flying from Winnipeg to Chicago is United Airlines.

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from Winnipeg to Chicago is February.

Dec 2024
Jan 2025
Feb 2025
Mar 2025
Apr 2025
May 2025
Jun 2025
Jul 2025
Aug 2025
Sep 2025
Oct 2025
Nov 2025

The cheapest day(s) of the week to fly from Winnipeg to Chicago is Friday.

Sun Sunday
Mon Monday
Tue Tuesday
Wed Wednesday
Thu Thursday
Fri Friday
Sat Saturday

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

Time Earliest
- Earliest
- Latest
Depart Earliest
- Earliest
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Arrive
- Earliest
- Latest
Duration
- Shortest
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Stopover
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14:15 YWG

16:45 ORD

2Hrs, 30m Direct
YWGWinnipeg J.A. Richardson Intl Airport 14:15 - ORD 16:45 2h 30m Direct
YWGWinnipeg J.A. Richardson Intl Airport 14:15
ORDChicago O'Hare International Airport 16:45
2h 30m
Direct
United Airlines (UA 5639)Embraer 175
United Airlines (UA 5639)
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- S
Embraer 175

06:45 YWG

12:58 ORD

6Hrs, 13m 1 Stop (YOW)
YWGWinnipeg J.A. Richardson Intl Airport 06:45 - ORD 12:58 6h 13m 1 Stop (YOW) Ottawa
YWGWinnipeg J.A. Richardson Intl Airport 06:45

YOWOttawa McDonald Cartier Intl Airport 11:25
YOWOttawa McDonald Cartier Intl Airport 10:20

ORDChicago O'Hare International Airport 12:58
6h 13m (1h 05m)
1 Stop YOW · Ottawa 1h 05m
Air Canada (AC 8110)Canadair Regional

United Airlines (UA 4437)Canadair Regional Jet 550
Air Canada (AC 8110)
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- S

07:30 YWG

14:51 ORD

7Hrs, 21m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 07:30 - ORD 14:51 7h 21m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 07:30

YYZToronto Lester B Pearson Intl Airport 14:00
YYZToronto Lester B Pearson Intl Airport 11:05

ORDChicago O'Hare International Airport 14:51
7h 21m (2h 55m)
1 Stop YYZ · Toronto 2h 55m
Air Canada (AC 260)Airbus A220 300

Air Canada (AC 505)Airbus A220 300
Air Canada (AC 260)
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07:30 YWG

13:11 ORD

5Hrs, 41m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 07:30 - ORD 13:11 5h 41m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 07:30

YYZToronto Lester B Pearson Intl Airport 12:20
YYZToronto Lester B Pearson Intl Airport 11:05

ORDChicago O'Hare International Airport 13:11
5h 41m (1h 15m)
1 Stop YYZ · Toronto 1h 15m
Air Canada (AC 260)Airbus A220 300

Air Canada (AC 503)Airbus A220 300
Air Canada (AC 260)
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- S

12:05 YWG

18:37 ORD

6Hrs, 32m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 12:05 - ORD 18:37 6h 32m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 12:05

YYZToronto Lester B Pearson Intl Airport 17:30
YYZToronto Lester B Pearson Intl Airport 15:35

ORDChicago O'Hare International Airport 18:37
6h 32m (1h 55m)
1 Stop YYZ · Toronto 1h 55m
Air Canada (AC 264)Airbus A220 300

United Airlines (UA 3542)Embraer 175
Air Canada (AC 264)
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- -
- -
- -
- -
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- -

12:05 YWG

19:32 ORD

7Hrs, 27m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 12:05 - ORD 19:32 7h 27m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 12:05

YYZToronto Lester B Pearson Intl Airport 18:35
YYZToronto Lester B Pearson Intl Airport 15:35

ORDChicago O'Hare International Airport 19:32
7h 27m (3h)
1 Stop YYZ · Toronto 3h
Air Canada (AC 264)Airbus A220 300

Air Canada (AC 509)Airbus A220 300
Air Canada (AC 264)
- -
- -
- -
- -
- -
- S
- -

12:15 YWG

19:37 ORD

7Hrs, 22m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 12:15 - ORD 19:37 7h 22m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 12:15

YYZToronto Lester B Pearson Intl Airport 18:40
YYZToronto Lester B Pearson Intl Airport 15:45

ORDChicago O'Hare International Airport 19:37
7h 22m (2h 55m)
1 Stop YYZ · Toronto 2h 55m
Air Canada (AC 264)Airbus

Air Canada (AC 509)Airbus A220 300
Air Canada (AC 264)
- -
- -
- -
- -
- -
- -
- S

12:15 YWG

18:37 ORD

6Hrs, 22m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 12:15 - ORD 18:37 6h 22m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 12:15

YYZToronto Lester B Pearson Intl Airport 17:30
YYZToronto Lester B Pearson Intl Airport 15:45

ORDChicago O'Hare International Airport 18:37
6h 22m (1h 45m)
1 Stop YYZ · Toronto 1h 45m
Air Canada (AC 264)Airbus A220 300

United Airlines (UA 3542)Embraer 175
Air Canada (AC 264)
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- T
- F
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- -

12:15 YWG

18:37 ORD

6Hrs, 22m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 12:15 - ORD 18:37 6h 22m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 12:15

YYZToronto Lester B Pearson Intl Airport 17:30
YYZToronto Lester B Pearson Intl Airport 15:45

ORDChicago O'Hare International Airport 18:37
6h 22m (1h 45m)
1 Stop YYZ · Toronto 1h 45m
Air Canada (AC 264)Airbus

United Airlines (UA 3542)Embraer 175
Air Canada (AC 264)
- -
- -
- -
- -
- -
- -
- S

12:15 YWG

19:32 ORD

7Hrs, 17m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 12:15 - ORD 19:32 7h 17m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 12:15

YYZToronto Lester B Pearson Intl Airport 18:35
YYZToronto Lester B Pearson Intl Airport 15:45

ORDChicago O'Hare International Airport 19:32
7h 17m (2h 50m)
1 Stop YYZ · Toronto 2h 50m
Air Canada (AC 264)Airbus A220 300

Air Canada (AC 509)Airbus A220 300
Air Canada (AC 264)
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14:50 YWG

22:07 ORD

7Hrs, 17m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 14:50 - ORD 22:07 7h 17m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 14:50

YYZToronto Lester B Pearson Intl Airport 21:00
YYZToronto Lester B Pearson Intl Airport 18:20

ORDChicago O'Hare International Airport 22:07
7h 17m (2h 40m)
1 Stop YYZ · Toronto 2h 40m
Air Canada (AC 266)Airbus

United Airlines (UA 5728)Embraer 175
Air Canada (AC 266)
- -
- -
- -
- -
- -
- -
- S

14:50 YWG

22:07 ORD

7Hrs, 17m 1 Stop (YYZ)
YWGWinnipeg J.A. Richardson Intl Airport 14:50 - ORD 22:07 7h 17m 1 Stop (YYZ) Toronto
YWGWinnipeg J.A. Richardson Intl Airport 14:50

YYZToronto Lester B Pearson Intl Airport 21:00
YYZToronto Lester B Pearson Intl Airport 18:20

ORDChicago O'Hare International Airport 22:07
7h 17m (2h 40m)
1 Stop YYZ · Toronto 2h 40m
Air Canada (AC 266)Airbus

United Airlines (UA 5728)Embraer 175
Air Canada (AC 266)
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- T
- F
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- -

16:30 YWG

23:11 ORD

6Hrs, 41m 1 Stop (DEN)
YWGWinnipeg J.A. Richardson Intl Airport 16:30 - ORD 23:11 6h 41m 1 Stop (DEN) Denver
YWGWinnipeg J.A. Richardson Intl Airport 16:30

DENDenver Intl Airport 19:40
DENDenver Intl Airport 18:07

ORDChicago O'Hare International Airport 23:11
6h 41m (1h 33m)
1 Stop DEN · Denver 1h 33m
United Airlines (UA 5623)Embraer 175

United Airlines (UA 1565)Boeing 737 800
United Airlines (UA 5623)
- -
- -
- -
- -
- -
- -
- S

16:30 YWG

23:09 ORD

6Hrs, 39m 1 Stop (DEN)
YWGWinnipeg J.A. Richardson Intl Airport 16:30 - ORD 23:09 6h 39m 1 Stop (DEN) Denver
YWGWinnipeg J.A. Richardson Intl Airport 16:30

DENDenver Intl Airport 19:40
DENDenver Intl Airport 18:07

ORDChicago O'Hare International Airport 23:09
6h 39m (1h 33m)
1 Stop DEN · Denver 1h 33m
United Airlines (UA 5623)Embraer 175

United Airlines (UA 1565)Boeing 737 900
United Airlines (UA 5623)
- -
- -
- -
- -
- -
- S
- -

16:30 YWG

22:51 ORD

6Hrs, 21m 1 Stop (DEN)
YWGWinnipeg J.A. Richardson Intl Airport 16:30 - ORD 22:51 6h 21m 1 Stop (DEN) Denver
YWGWinnipeg J.A. Richardson Intl Airport 16:30

DENDenver Intl Airport 19:20
DENDenver Intl Airport 18:07

ORDChicago O'Hare International Airport 22:51
6h 21m (1h 13m)
1 Stop DEN · Denver 1h 13m
United Airlines (UA 5623)Embraer 175

United Airlines (UA 2258)Boeing 757 300 Series
United Airlines (UA 5623)
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16:30 YWG

22:51 ORD

6Hrs, 21m 1 Stop (DEN)
YWGWinnipeg J.A. Richardson Intl Airport 16:30 - ORD 22:51 6h 21m 1 Stop (DEN) Denver
YWGWinnipeg J.A. Richardson Intl Airport 16:30

DENDenver Intl Airport 19:20
DENDenver Intl Airport 18:07

ORDChicago O'Hare International Airport 22:51
6h 21m (1h 13m)
1 Stop DEN · Denver 1h 13m
United Airlines (UA 5623)Embraer 175

United Airlines (UA 2258)Airbus A321 Neo
United Airlines (UA 5623)
- -
- -
- -
- -
- F
- -
- -

16:30 YWG

22:36 ORD

6Hrs, 06m 1 Stop (DEN)
YWGWinnipeg J.A. Richardson Intl Airport 16:30 - ORD 22:36 6h 06m 1 Stop (DEN) Denver
YWGWinnipeg J.A. Richardson Intl Airport 16:30

DENDenver Intl Airport 19:05
DENDenver Intl Airport 18:07

ORDChicago O'Hare International Airport 22:36
6h 06m (58m)
1 Stop DEN · Denver 58m
United Airlines (UA 5623)Embraer 175

United Airlines (UA 2258)Boeing 757 300 Series
United Airlines (UA 5623)
- -
- -
- -
- -
- -
- S
- S

16:30 YWG

23:57 ORD

7Hrs, 27m 1 Stop (DEN)
YWGWinnipeg J.A. Richardson Intl Airport 16:30 - ORD 23:57 7h 27m 1 Stop (DEN) Denver
YWGWinnipeg J.A. Richardson Intl Airport 16:30

DENDenver Intl Airport 20:25
DENDenver Intl Airport 18:07

ORDChicago O'Hare International Airport 23:57
7h 27m (2h 18m)
1 Stop DEN · Denver 2h 18m
United Airlines (UA 5623)Embraer 175

United Airlines (UA 377)Boeing 737 900
United Airlines (UA 5623)
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- -
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- -
- F
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16:30 YWG

23:57 ORD

7Hrs, 27m 1 Stop (DEN)
YWGWinnipeg J.A. Richardson Intl Airport 16:30 - ORD 23:57 7h 27m 1 Stop (DEN) Denver
YWGWinnipeg J.A. Richardson Intl Airport 16:30

DENDenver Intl Airport 20:25
DENDenver Intl Airport 18:07

ORDChicago O'Hare International Airport 23:57
7h 27m (2h 18m)
1 Stop DEN · Denver 2h 18m
United Airlines (UA 5623)Embraer 175

United Airlines (UA 377)Boeing 737 Max 9 Passenger
United Airlines (UA 5623)
- -
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- -
- -
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Sorry, there are no schedules matching your filters. Try removing one. reset

What’s the fastest flight time from Winnipeg to Chicago?

The fastest flight time for direct flights from Winnipeg to Chicago is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.

What’s the most popular airline flying from Winnipeg to Chicago?

The most popular airline flying from Winnipeg to Chicago is Air Canada. Find the latest flight deals on Wego.

How far is Chicago from Winnipeg?

The flight distance between Winnipeg and Chicago is 1154km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 06:45. The last flight of the day departs at 06:45. See the full list of flight times on Wego.

How many airlines offer direct flights from Winnipeg to Chicago?

There are 1 airlines that offer direct flights from Winnipeg to Chicago. Find out the list of airlines on Wego.

Popular Airlines flying from Winnipeg to Chicago

Air Canada ‏()

SkyWest Airlines ‏()

United Airlines ‏()

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Popular Destinations from Winnipeg

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