Road trip: Toronto to Chicago – 6 Must Do’s

spellbound travels toronto to chicago roadtrip the bean

When life in Canada gets a little dull it’s quite easy for us Torontonians to take a little trip down south to the States! If you’re not up for too long of a drive, your options are somewhat limited. Boston, New York and Chicago are probably your best bet when it comes to weekend/quick getaways! See why Toronto to Chicago has been my favourite road trip so far …

1. Two for One 

The classic route from Toronto to Chicago involves passing through Michigan. It’s a great opportunity to stop in Detroit and see a new city along the way. If you’re tight for time you can always opt to pass through but I’m always game for seeing more!

The entire journey from Toronto will take around 8 hours depending on when you leave so if you’re planning to stop in Michigan you may want to spend a night or two there before you continue on your journey. 

2. Cubs Game

spellbound travels cubs game wrigley field

A trip to Chicago wouldn’t be complete without attending a Cubs game at Wrigley Field. Now of course this isn’t doable during the off season but if you’re planning a trip during the summer, it’s a great chance to catch a game! You can find information regarding tickets and pricing here

3. Deep Dish Pizza

Okay, I may have spoke too soon … Deep dish pizza holds the title as an absolute MUST when you’re in Chicago and it can be enjoyed anytime of year! It’s deep rooted history offers quite an interesting story you can learn more about while chowing down on pizza.

Be warned, you probably won’t be able to finish one slice on your own! I personally got my little slice of heaven from Uno Pizzeria – the first deep dish restaurant in Chicago. Here’s a few other spots you can check out!

4. Stroll Around the Windy City 

No matter the time of year you choose to explore Chicago, there’s lots to do around the city. The Chicago River runs through the city and gave me a little bit of a Melbourne feel. You can go on a boat tour through the river or watch as they dye the river green for St. Patty’s day each year!

You can’t miss out on getting a picture by ‘the bean’. The bean is more formally known as Cloud Gate at Millennium Park and attracts tourists year round. I was there during the festival Lollapalooza so it was a little more hectic than usual.

5. Beach Day 

If you’re headed to Chicago during the summer, a beach day is necessary. Unlike the typically dark/gross looking water you find along the Lake Ontario beaches, Chicago sits along Lake Michigan. The water is so clear and there are heaps of beaches near the city! 

I’d recommend hitting up Ohio Street Beach as it’s right along Lakeshore and a great spot for 20 somethings.

6. Rooftop Drinks/Bar Hopping 

Like any city, you’ll find a nice array of bars to check out during your stay. If you’re day drinking, I found bars around the Chicago River to be the best for atmosphere! On the other hand, if you’re going out for drinks at night, definitely go for a rooftop. West Loop seems to be the best spot for cocktail bars but just ask any local and they’ll happily give you their recommendations.

Chicago was one of those cities I can imagine visiting again and again! My first time there was when I went to visit a friend I met abroad and it felt exciting but familiar at the same time. Maybe my next road trip will be a winter trip to the windy city! If you’ve been to Chicago and have any other tips for a road trip from Toronto to Chicago feel free to connect with me on Instagram! Until next time .. 


Amy xx

Leave a Reply