A Chicago Winter Road Trip from Toronto

Chicago is the jewel of the Midwest; a huge city with beautiful architecture, an abundance of culture and a gleaming nightlife. The city is a hop, skip and a jump by plane, or a fun filled 8-hour road trip away! If you’re headed to the city for stopover on your way to another part of the USA, or if you are planning a city break, here are some fun things you can do in just a few days in the “Windy City.”

We buckled up in the heated seats, were locked and loaded with winter tires and ready to tackle the 835 Kilometre journey in our Honda Civic Sedan that we accessed from the press fleet. Setting off at midday and grabbing food on the road, we arrived at our home for the next few days, The Urban Holiday Lofts, by 9pm.

Honda Civic Sedan arrived in Chicago

Wicker Park, Bucktown and Logan Square

Wicker Park is one of the coolest parts of town and, as well as cool vintage shops, there are some excellent spots to have breakfast, lunch and dinner around the Damen Transit stop. Reading and raring for our first day exploring the city, we popped in to The Bongo Room, a much-loved Wicker Park institution since 1995. The coffee is refillable and the breakfast burrito is a winner every time! If you feel like spicing up your breakfast, they also serve an array of delicious cocktails.

Wicker Park, Bucktown and Logan Square is where you will find the bright young things of the city dipping in and out of dive bars, come jazz bars, come comedy clubs. Food and drinks out this way are cheaper than in the heart of the city, with the nightlife radiating a somewhat more authentic vibe. There is a great spot called Gallery Cabaret in Bucktown, which we found hosted an excellent jazz night on a Monday.

Monroe Harbour, Lake Michigan

Take the Chicago Transit down to Monroe and walked a few blocks to the lakefront, to survey the Monroe Harbor of Lake Michigan. In the summer, the harbour is home to luxury yachts, and in the winter it is a safe bet it will be frozen! As beautiful in the winter as it is the summer, there is something quite breathtaking overlooking such a huge body of water, one of five in North America, and bigger in size than our own Lake Ontario.

Monroe Harbor, Chicago
Monroe Harbor, Chicago

In the summer, other lake front attractions include the Navy Pier and Montrose beach further up town.

The Art Institute of Chicago and the Millennium Park

The Art Institute of Chicago is one of the most impressive (and largest!) art museums in North America, with extensive collections of over 300,000 works. For me, a quick hop through my favourite Impressionists always leads me to hours spent browsing the Modern sections.

The Art Institute is $21 dollars admission, but can be combined in a package with other attractions. That said, careful when buying a package ticket as some savings are not necessarily worth it.

Cloud Gate, Millennium Park

Close by to the Art Institute, we walked to the Millennium Park, a new art and architectural space built to celebrate the second Millennium. It is here you will find the famous bean landmark, officially known as Cloud Gate.

Millennium Park, Chicago

Signature Room at the John Hancock Tower

Many head up the Sears Tower or even the Observation Deck at the John Hancock tower to experience excellent views of the city. One recommendation I would make is, instead of paying the $25 fee to access these viewing platforms, head to the free to access Signature Room at the John Hancock tower and invest your money in a cocktail instead.

The John Hancock Tower in Chicago
The John Hancock Tower in Chicago

The views are comparable, and you’ll get to enjoy a drink as you take in the views! The best time to go, if possible, is around 30 minutes before sunset, that way you can see the city in both the day and night, whilst watching the sun set over the pavements. Cheers to that!

Views from the John Hancock Tower
Views from the Signature Room, John Hancock Tower

Deep Dish Pizza

Of course, a trip to Chicago would be all but incomplete without a hearty slice (or three!) of classic Chicago deep-dish pizza. We ventured to local favourite, Lou Malnati’s and ordered a large Malnati’s Chicago classic, which was a delectable treat!

The City of Crime

If you’re interested in the history of arguably the world’s most notorious crime city, the Chicago Crime Tour offers twice daily bus tours to show you the sights. You’re taken to some of the dark hotspots and told stories of the cities more grizzly side including the notorious activities of John Dillinger and Al Capone.

Seeing the Sights on the Chicago Crime Tour
Seeing the sights on the Chicago Crime Tour

Pine Knob Ski Resort

On the drive back from Chicago to Toronto, we decided to stay an evening in Auburn Hills so that we could have a days skiing at the Michigan based Pine Knob Ski Resort. It is on route back to the city and is great for 5-8 hours of easy, fun skiing. A day’s lift pass at the resort was approximately $40 and ski rental is $30.

Honda Civic Sedan at Pine Knob Ski Resort
Honda Civic Sedan at Pine Knob Ski Resort


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About Rebecca Felgate 121 Articles
Writer for Toronto Guardian