Attribution: By ABC Television (eBay item photo front photo back) [Public domain], via Wikimedia Commons

If you’ve ever thought, “Nothing screams sibling rivalry like the complicated relationship between Chicago and Toronto,” well… you might be the first. In fact, we’d be willing to bet that most people have no idea Chicago and Toronto are sister cities. In a world where there is only so much limelight to go around, the Windy City is the Marcia Brady to Toronto’s Jan. Sure, Marcia gets all the attention and pom-pom trophies her beauty demands, but Jan deserves more than a fake boyfriend named “George Glass” and an inferiority complex. Come on, you always rooted for Jan and you know it.  So here’s the story, of a lovely…pair of cities (don’t worry, it’s not all “Chicago, Chicago, Chicago!):

Good Grub from Chicago to Toronto 

Photo attribution: Flickr/Creative Commons/Jeremy Keith/Via/https://flic.kr/p/2TQzGp

Photo attribution: Flickr/Creative Commons/Jeremy Keith/Via/https://flic.kr/p/2TQzGp

Look, it doesn’t matter if “foodie” is your middle name or not – a person’s gotta eat. It is in this category that Chicago most eclipses the reputation of Toronto in Marcia-like fashion. Deep-dish pizza, ballpark franks, and gourmet burgers all come to mind when you imagine a trek to Chicago. But did you know, fair reader, that Toronto is a smorgasbord of culinary delights in its own right? It has three Chinatowns, one Little India, and plenty of French culture and cuisine. That’s right, Marcia, Toronto can cook too, okay?

Famous Sights

B1_3_Skyline of Toronto over Ontario Lake at twilight

If Peter was throwing a football at Chicago’s nose, it would land smack-dab in Millennium Park. This 25-acre green space is easily the face of Chicago, and while it may not have Marcia’s teen model aspirations, it does boast plenty of aesthetic appeal. Always one to show off, this Marcia-like city also has an amusement park on Navy Pier and a shopping stretch so grand it dares to call itself the Magnificent Mile.

In true Jan Brady fashion, Toronto has something to prove when compared to the wonders of Chicago. Sister cities are nothing if not, ahem, friendly competitors, after all. Instead of adding Nair™ to Marcia’s shampoo, this oft-overshadowed sister built a 116-story building called the CN Tower. St. Lawrence Market and educational spots like the Ontario Science Centre can also keep you busy.

How to Get Around

Photo attribution: Flickr/Creative Commons/H. Michael Miley/Via/https://flic.kr/p/apL14v

Photo attribution: Flickr/Creative Commons/H. Michael Miley/Via/https://flic.kr/p/apL14v

Naturally Chicago has an elevated train system; Marcia won’t be driven underground where no one can see her. While not all of the “L” trains are above-ground at all times, the system does include a lot of elevated rails. You can also see Chi-Town by bus or land and water taxi. On the other hand, Jan always did like to have an escape route in all circumstances. She just never knew when Marcia was going to accuse her of being friendless or “George” was going to “call.” In that spirit, Toronto has a convenient underground walkway called PATH that links many shopping and entertainment centers. In all, the walkway is 16 miles. Of course, you can always see this Canadian gem by bike, taxi, or streetcar.

One Thing You Can’t Miss 

Photo attribution: By Sergiu Dumitriu (Own work) [CC BY-SA 3.0 (http://creativecommons.org/licenses/by-sa/3.0)], via Wikimedia Commons

Photo attribution: By Sergiu Dumitriu (Own work) [CC BY-SA 3.0 (http://creativecommons.org/licenses/by-sa/3.0)], via Wikimedia Commons


From Toronto to Chicago, every city has one attraction you absolutely must experience. In Chicago, a certain shiny bean has made its way to many a Facebook profile pic. Officially called Cloud Gate, you can see your own reflection in the steel art installation—just the way Marcia would like it. If you have but a few hours to visit Toronto, and we hope that’s never the case, the observation decks at CN Tower should be your priority. Make Jan proud by braving a trip out to the glass-bottom terrace. You can really show up Marcia by putting on your big-kid undies and strapping into the hands-free EdgeWalk at the top of the tower.

There are no other sister cities like Chicago and Toronto. We like to think of them as the Marcia and Jan of our modern times, two equally fun and affable destinations with metaphorical hair of gold and a strong partnership. Whether your route takes you from ORD to YYZ or from YYZ to ORD, it’s much more than a hunch that you’ll have a good time.