
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $312 (Kiwi.com) |
One-way from | $155 (Mytrip) |
Popular in | January |
Cheapest in | May |
Average price | $712 |
Good round-trip deal | $1,004 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Do 5/7
10:30 am-7:49 pm
1 stop9h 19m
Winnipeg
So 5/10
7:00 pm-9:45 am
1 stop14h 45m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Di 5/5
11:48 am-7:49 pm
1 stop8h 01m
Winnipeg
Mi 5/6
9:20 am-4:18 pm
1 stop6h 58m
ChicagoWinnipeg
ORD - YWG
ORDYWG
Chicago O'Hare Intl
Mi 5/6
9:50 am-7:49 pm
1 stop9h 59m
Winnipeg
Sa 5/9
9:20 am-4:18 pm
1 stop6h 58m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Fr 4/10
4:05 pm-11:13 am
2 stops19h 08m
Winnipeg
Mo 4/13
12:20 pm-12:43 pm
2 stops24h 23m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Do 5/7
9:22 am-5:15 pm
2 stops7h 53m
Winnipeg
So 5/10
6:40 am-1:19 pm
1 stop6h 39m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Mi 7/8
9:49 am-4:52 pm
1 stop7h 03m
Winnipeg
Di 7/14
12:46 pm-6:18 pm
1 stop5h 32m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Do 4/16
9:27 am-8:40 am
2 stops23h 13m
Winnipeg
Di 4/21
5:00 am-5:58 pm
2 stops12h 58m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Mi 5/13
3:20 pm-5:58 pm
2 stops26h 38m
Winnipeg
Mi 5/20
11:40 am-2:35 pm
2 stops26h 55m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Do 4/9
11:00 am-11:13 am
2 stops24h 13m
Winnipeg
So 4/12
8:05 pm-8:47 am
2 stops12h 42m
ChicagoWinnipeg
MDW - YWG
MDWYWG
Chicago Midway
Di 5/12
1:59 pm-10:54 am
1 stop20h 55m
Winnipeg
Sa 5/16
10:45 am-8:43 am
2 stops21h 58m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 28% on airfare.
The most flights from CHI to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
Comfort
Crew
Entertainment
Food
Boarding
Overall
Reviews
Dane,Jan 2026
TYS - IAD
Comfort
Crew
Entertainment
Food
Boarding
Overall
Reviews
Dane,Jan 2026
TYS - IAD
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$356 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$226 | Average$509 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$263 | Average$649 | FlexibilityNo cancel fee | On-time69% |