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Lowest round trip fares by airline from Chicago and Winnipeg

Cheapest prices ($358 One Way, $453 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Winnipeg

The Marlborough Hotel

The Marlborough Hotel

2 out of 5
331 Smith St, Winnipeg, MB
Stay at this hotel in Winnipeg. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
4.8/10 (1,000 reviews)
"It’s not open. Booked in December, was never notified of its temporary closure due to a police investigation. Probably don’t stay there even when/if it reopens."

Reviewed on Feb 11, 2024

The Marlborough Hotel
Super 8 by Wyndham Winnipeg West

Super 8 by Wyndham Winnipeg West

3 out of 5
3760 Portage Ave, Winnipeg, MB
The price is $91 per night from May 5 to May 6
$91
per night
May 5 - May 6
Stay at this 3-star business-friendly hotel in Winnipeg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,005 reviews)
"Incredibly clean and very nice property. The rooms are perfectly suitable and they are completely clean and quite comfortable."

Reviewed on Apr 24, 2024

Super 8 by Wyndham Winnipeg West
Assiniboine Gordon Inn on the Park

Assiniboine Gordon Inn on the Park

3 out of 5
1975 Portage Ave, Winnipeg, MB
The price is $66 per night from Apr 28 to Apr 29
$66
per night
Apr 28 - Apr 29
Stay at this 3-star business-friendly motel in Winnipeg. Enjoy free WiFi, free parking, and a nightclub. Our guests praise the breakfast and the helpful staff ...
6.8/10 (963 reviews)
"By chance I came across this Assiniboine Gordon Inn at very last minute of my going to Winnipeg on Expedia , but to be sincerely, the place is very lovely, i was ask to pay $250 for security incase any damage happens and i checked out leaving the room in good condition and my $250 was refunded into ..."

Reviewed on Apr 22, 2024

Assiniboine Gordon Inn on the Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Winnipeg

Origin
Chicago
Destination
Winnipeg
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
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Chicago to Winnipeg

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.