Taking a Road Trip From Winnipeg to Chicago

On Spring Break we wanted to go somewhere but after our vacation to Philippines and Japan and with Miami and the Bahamas coming up in the summer we decided to save some money.  Which cool city could we go to and save money on flights?  Chicago is famous, it’s only a 13 hour drive and I’ve never been, so we planned our road trip!

Before you read any further, you can watch my VLOG here.

The trip from Winnipeg isn’t bad, you can stop in Grand Forks or Fargo for lunch; we stopped at Chick-Fil-A in Fargo and then stayed our first night in Minneapolis.  Instead of staying downtown and partying, we decided to go the family route.  We stayed near the Mall of America, went to the mall, walked around, bought our baby her first Teddy Bear then had a good old fashioned American meal. 

The next morning there was a big winter storm coming, and there was also snow that blew in overnight.  We timed it perfectly, we left around 8 am, and followed the first wave of snow.  The roads were rough, but if we had left earlier, we would have been driving through the first wave of snow, and if we left any later, we would have been stuck in the real storm.  Minneapolis had 11 inches; we were lucky we left when we did.  As for the route to Chicago from Minneapolis, there are pretty much two options: the way with tolls, which is about 30 minutes quicker, or the road without tolls, which passes through Milwaukee.  We wanted to get to Chicago quickly so decided that on the way home we’d go through and check out Milwaukee and on the way there I’d have a few US dollars ready for the toll booths.  Word of advice the spare dollars I had were useless, you need to pay online ahead of time.  And whichever way you go, you will pass through Wisconsin Dells, another cool town to checkout.  There are museums, shops, lots of restaurants and of course water slides.  It was still cold so we looked around, grabbed a coffee and a snack and kept on our way.

Finally, we arrived in Chicago.  We stayed in the Hyatt Place in River North which was an amazing hotel.  Not only was the hotel amazing but so was Chicago, it is one of my favorite cities I’ve been to.  I didn’t think I’d like it that much, but I did.  On the way in I was amazed at the skyline and buildings.  We stopped for gas and you could even get a beer and play VLT’s in the gas station which was kind of cool.  Anyways, in Chicago there is amazing architecture and awesome food with lots of variation (but be prepared to gain a few pounds).  Chicago is safe (where you will be staying and hanging out) and there is lots to do.  There is the Navy Pier with the Ferris Wheel, the Children’s Museum, The Shedd Aquarium, Adler Planetarium, a number of worldly renowned museums, the Bean, The River Walk, Architecture boat cruises, Lake Michigan and its beaches, the Willis Tower, lots of professional sports teams and good shopping.  I will talk more about the things to do in another blog. And, if you're a fan of Dick Wolf's One Chicago Series, or Chicago PD and Fire, there are a number of iconic locations to check out.  To find out more about that click here.

And when people say don’t drive in Chicago, they aren’t talking to Winnipeggers.  One of the biggest complaints is the one-way streets in downtown, but we are used to them.  We didn’t drive a lot there, except for one day where we went all over the place, and it was quick and easy to drive and get around.  If you can drive through one-way streets then you’ll be fine.  The only negative is parking is expensive, we ended up paying $58 USD a night for parking in River North.

We stayed 4 nights, which was perfect.  We did a lot of activities, ate a lot, and saw a lot of places; maybe one more night would have allowed us to go at a slower place and see one or two more things, but 4 days was fine.  Although, there were just a few more dishes and restaurants we’d have liked to try.  The food was amazing, and you can watch my food VLOG later this week.

On our final morning, we were debating on leaving early. We had a 6 and a half hour ride to Minneapolis where we’d stop again, plus we wanted to stop for lunch in Milwaukee.  Instead, we decided to go to the world’s largest Starbucks, the Starbucks Reserve Roastery and do one last walk down Magnificent Mile and the River Walk.  The Starbucks was cool and there is a wide variety of foods and drinks, including alcoholic.  It was a nice morning to end our vacation in Chicago.

We ended up leaving late, but the weather was good and we weren’t too concerned about the ride.  And we arrived in Milwaukee at a perfect time for lunch.  The ride was about half an hour longer, but the route through Milwaukee avoids tolls and it was an easier and slower paced drive.  Milwaukee was a cool city and somewhere I’d have liked to spend more time.  It really looks like a midwestern city, has a good skyline of its own and has really cool looking freeways.  We stopped in the Milwaukee Public Market, had lunch and bought some famous Wisconsin cheese.

After that we headed back to Minneapolis.  We arrived at our hotel in downtown Minneapolis in the evening.  We booked a hotel downtown on the way home in an attempt to enjoy a good meal in downtown Minneapolis.  We were too tired from the action-packed vacation and the ride so decided to eat at the hotel and call it a night.  That’s okay because it was a weekday with no sporting events so downtown hotels were reasonably priced and much cheaper than on a weekend and especially a weekend of a Viking’s game.

The next morning, we were off for another 7-hour ride home with a stop in Fargo for lunch.  Overall, it was an amazing road trip and one I’d recommend.  You can save money on flights and visit an amazing city in a reasonable time frame while driving from Winnipeg.  You can break the ride up with a stay in Minneapolis and/or stops in Grand Forks, Fargo, Wisconsin Dells and Milwaukee.  It is a smooth ride with no stopping except to eat and refuel and there’s a lot to see in and on the way to and from Chicago.