Having just returned from Malaysia and having been to North Dakota, I am happy to add my bit to this query.
I hope you realize how cold it can be in North Dakota in the period you mentioned and that there may be snow storms and blizzards and that you have to be especially prepared if you are driving on the main roads (dont dare drive on smaller roads).
by road is the easiest route to from Dickinson via Bismark to Winnipeg
it is about 800 km one way.
there are flights from BIS to Winnipeg connecting via Minneapolis. it will take time also and you can expect to pay around 400 usd for round trip since these routes are not well served.
if you are going with friends, driving would be a good option but then again take into consideration the conditions of the road. I find driving in winter rather treacherous because of the ice on the road. but the natives of the area seem to manage very well.
Winnipeg Transit system is a reliable one to use to get into places around the city if you don't have your own Car. Buses Number 1 to 3 are free of charge that goes around downtown or the city proper.
You have to be on the designated Bus Stops before the scheduled time of arrival. You can buy a Weekly Pass, Monthly Pass or Bus Tickets( Minimum of 10) from convenient stores. You can pay 2.40 CAD if you don't have a pass. Pay exact amount because bus drivers don't give change. You can call the telephone number written on Bus stop signs to locate your bus or visit their website and from there you can plan your trip. Just type the origin and the destination and the time you plan to leave or arrive and it will create your trip plan and just follow the instruction. There are also free brochures for every route number on convenient stores by the way.
There's also a bustxt service they are calling. Just compose a message using "times","stops", or "bus" commands then send it to 204287898 and you will receive a response in seconds.
I am a regular bus user since I am new here in Winnipeg and I went to many places here just by riding a bus. I plan my trip on their website.
If you want to get around, you've got to have your own vehicle. As long as you have someone with a map to help you navigate, you'll be fine. You have the freedom to come and go as you please, just don't get too drunk at the bars and clubs, otherwise you'll have to taxi home and back in the morning to get your car. THAT'S expensive.
This one is another option though a bit expensive for me. If you are in hurry this will be the solution. There are a number of taxi companies operating in Winnipeg and one of them is Duffy's taxi.
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