Chicago 3.0

They say ‘third time’s a charm’, but for me, the first was all it took. Chicago had me at hello, and I’ve proclaimed my affection for it ever since. I most certainly like Chicago more than New York, believing that Toronto is much more like a mini-Chicago than the “Little Apple”. I love Chicago’s neighbourhoods, its food, and its waterfront. I love its architecture, its parks, and its heritage. I love its sense of humour, self-awareness, and authenticity. I just love it.

This summer, I went back to Chicago for the third time, this time with my boyfriend who’d never been. Feeling rather unpatriotic, we took off on the Canada Day long weekend, jumped on Porter (my fave), and took up residence at the Fairmont Millennium Park (another fave) for four days. We had some epic plans, and I was determined to show off my favourite spots, discover new ones, and fulfil one of my childhood dreams. In four days. Boom.

Chicago theatreClassic Chicago.

What’s worth doing again?

The Architectural Boat Cruise. There are several companies you can go with, but I’ve gone with Chicago Line twice. Both times the guides have been fantastic, and this itinerary goes a bit further up the river than the other ones (from what we were told). It’s also super convenient to walk from the Fairmont, so thumbs up there. I’d do this tour again and again, because there’s just nothing like it. I don’t care if it’s touristy – it’s awesome.


Chicago Architecture Marina City as seen from the Chicago Architecture Boat Cruise

Millennium Park. Our gorgeous hotel room overlooked the park (bonus) and it really is one of the best urban parks around. The Bean is cool every single time, because it never ever looks the same, and I love watching people’s reactions when they watch the Millennium Fountain for the first time.

The Bean ChicagoReflection under the Bean

Chicago Cultural Center. Across the street from Millennium Park the Chicago Cultural Center is full of incredibly beautiful mosaics, and is one of the best things in Chicago. It’s free, and you’re welcome to wander around as you please, so be sure to go upstairs and check out the largest Tiffany dome in the world (I dare you not to say “wowwwwwwww”). When you leave, keep your eyes peeled for Puppet Bike. We didn’t see it this time, but it’s actually my favourite thing about Chicago, hands down.

chicago tiffany domeTiffany dome in the Chicago Cultural Center

chicago cultural centerOne of the many gorgeous mosaic quotes in the Chicago Cultural Center

What was new?

Bucktown and Wicker Park. Chicago is all about its neighbourhoods, so we left The Loop and headed northwest to hipster-ville. Some of the coolest-sounding restaurants were in Bucktown and Wicker Park, so I was on a mission to find great food for good prices (I love you, Blackbird, but I just can’t afford you…). This meant trying to get into Big Star three times (two-and-a-half hour waits!) before finally scarfing down their ridiculously delicious and cheap tacos while standing next to barrels by the bar (seriously). We sat up at the bar at The Southern and got some great local advice from the bartenders, and we stumbled across a beer festival somewhere else nearby.

wicker parkWicker Park from the Blue Line platform

Running tours. I like to pretend that I’m going to be fit while I travel. Sometimes it happens, most times it doesn’t. I told myself I’d do one of these running sightseeing tours, but I preferred to drink wine every night instead. Alas, someday, running tours, someday!

But what’s the best?

Going to a Cubs game. My favourite movie is A League of Their Own. I’ve loved it since I was a tiny little softball player, and ever since I can remember, I’ve wanted to go to a game at Wrigley Field. I’ve done a stadium tour, but never a game. This was the first time the Cubs were in town at the same time I was, so there was no way we weren’t going. Tickets are way more expensive than Jays tickets (ah, the beauty of an over-sized baseball stadium in a hockey city), but we got great tickets three levels up, halfway down the first base line, about 20 rows back, for $50.

wrigley field instagramWrigley Field!

We spent Canada Day watching the Cubs beat the Astros 1 – 0. It wasn’t the most exciting game, but I didn’t care in the least. I was at Wrigley. It was exactly as I’d expected it to be – it’s a real American ballpark, with the Dixieland band working their way around the stands, and Take Me Out to the Ballgame being sung with more enthusiasm than the national anthem. The beer was cheap, the sun was shining, the stadium was full (what a novel idea), and I was fulfilling a long-time dream.

cubs win wrigley fieldCubs (and Chicago) FTW!

Chicago, you’ve been very good to me. Love you long time.

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