how to see a sliver of chicagoland in 2.5 days


Drive to the GO Station.
Leave your car.
Take the train to Toronto.
Sit next to a guy who works for the TTC and who has an intercom system in his house so he can contact his children when it’s time for dinner. Discover this and other details of his life. He is a wonderful travelling companion and once at Union Station knows the way to the shuttle bus for Porter Airlines.
Get on said shuttle.
Get on ferry to Toronto’s Billy Bishop tiny island airport.

Make mental note to write a letter. “Dear Porter Airlines: I’m very cross with your greedy antics in trying to expand the island airport. It, and you, happen to be perfect as is.”
Although arriving an hour early, be the last one to board the plane. Blame the free salted almonds and comfy armchairs.

Fly into Chicago’s [also perfect in its smallness] Midway airport where you will be serenaded with the blues.
A cab ride into the city takes about half an hour.
You’ll know when you get there by the sound of the el trains.
Because you know somebody who knows somebody who knows somebody, get a room in a historic building at the southern end of The Loop where you are practically the only guests. This is the Chicago way.
Go outside.
And discover that you are on a Great Lake. Not like in Toronto, but for real.

If you’ve got a serious chess habit, be happy; you’re in the right place.
Take time for reflection.
And music.
Discover neighbourhoods in the middle of downtown with off-leash dog park, running track, ball diamond. Try not to look impressed.

Discover a palace filled with fresh food—local ramps, dried grapes still on the vine, rows and rows of olive oil, fruit and veg you’ve never heard of, two dozen kinds of mushroom, cheese, pasta, seafood, home-made gelato, chocolate, bread.
Be sorry you don’t have a kitchen in your historic room.

Be happy there are places to eat in the food palace.
Walk some more.

Find the Tiffany ceiling in the old Marshall Fields [now Macy’s] building. Be prepared for staff who do not know what you mean when you say ‘Tiffany ceiling’. What you mean is the ceiling made in 1907 by Tiffany & Co. using 1.6 million pieces of favrile glass. It took something like 50 men and 18 months to install. The best view is from the 5th floor lingerie department, but you can see it from the first floor also, by looking ‘up’.
Looking up  is good advice generally.
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But not mandatory.
Have dinner at Boka.
Have the octopus as a starter and if you have room have it again for dessert then take your happy belly to City Winery, a combination restaurant and music venue. Something like Hugh’s Room, but bigger.

On the way home, get some tea from the place down the street. Give the woman who’s bedding down on the sidewalk some money.

Look out your window at 3 a.m. and see the definition of not a creature was stirring…
Look again a few hours later.
When your window turns golden it’s time to get up. Be grateful you’re facing east.
Ask people on the street where the diner Lou Mitchell’s  is and when they don’t know and you explain that it’s legendary, that it’s where Route 66 began—and they still don’t know—realize you’re probably too far away to walk. Get a cab.

Enjoy the Milk Duds and doughnut holes they give you as you walk through the door.  Also the single prune and slice of orange that comes with every order.
Be thrilled to find a cab waiting outside the diner when you leave. Jump in and then be annoyed that you forgot to walk over to Daley Plaza, near Lou’s, to see the Picasso sculpture, Chicago’s first piece of outdoor art.

Of which there are now oodles.
Not the least of which is The Bean, which 10,000 people told you to see.

So see it.
Console yourself about the Picasso thing with a visit to the Museum of Contemporary Art. 

Discover Vivian Maier in the magnificent book section of the gift shop.IMG_6115_1
Take a seat on the bench in front of a series of full length windows by Marc Chagall.
Do NOT take a seat on the pink box.
It is NOT for sitting. It is art.
Be glad you asked.
And then pretend you knew all along…
Go back to the palace of food to look at the olives. Share a kale salad before heading to Giordano’s for pizza. The salad will tide you over while you wait in line. Leave with half a Giordano’s pizza in a box. Ask the woman who lives on the street if she’d like some pizza. She will say I won’t complain. And as you walk away you’ll hear her friend say Give me a slice…

Take the architecture boat tour.

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Be a little surprised at how much water is in and around this city.
Stop by to see Vincent...
and friends.
And then walk some more.
Walk all the way to the beach. One of the beaches.

There are 26 miles of beach.IMG_6150
Meet a hacky sack guy who takes pictures of himself hacky sacking and wonders why more people aren’t curious about what he’s doing. In exchange for your curiosity he will offer you a hot tip: Ghiardelli’s gives free chocolate samples. IMG_6290

Forget to ask where Ghiardelli’s is and then decide that wherever it is it’s too far to walk.

Make a note to rent a bike next time.
Be amazed by it all and worn out and belly-filled and happy. And remember the things your neighbour from Chicago told you. About the other end of The Loop. About the other 25 miles of beaches, The Field Museum, street food and Frank Lloyd Wright. About tiny tucked away neighbourhoods where the ‘real’ Chicago lives. Realize that, despite all you’ve seen, you’ve seen almost nothing…

Wear pin-stripes.
At least once.

More travel here.

21 thoughts on “how to see a sliver of chicagoland in 2.5 days

    1. Well, I can tell you I was surprised by how much I liked it. I was expecting merely to be soothed by the art and bristling about everything else. Not the way it turned out. Nothing’s perfect of course, but I’m impressed with the way they use the downtown core. So much smarter than what Toronto’s done. And not just the waterfront, but the way they’ve preserved the architecture and how cleverly they’ve built the city… they have ‘lower’ roads through the city centre for trucks and delivery vans, etc., so the main streets aren’t clogged. They incorporate parking and river access with their buildings. Art is everywhere. They’re creating yet another park downtown. A farm garden. I could go on…

  1. Oh my. The Tiffany ceiling. Lou Mitchell’s. All of it. I didn’t know until this moment how deeply I need to visit Chicago.

    I thoroughly enjoyed the tour, Carin, thank you. But damn you for making me need to visit Chicago. Don’t you know I hate cities?

  2. Agog and delighted as always. No one packs as big a punch into a whirlwind trip as you do. You and your camera and sense of humour.

    1. I was agog also. I’d heard about their waterfront but wasn’t prepared for how really innovative it is. Such a pleasure to walk. Though on another visit, I’d definitely consider bikes. Plenty of dedicated paths.

  3. Well that was good fun. I am enjoying the visuals that you pair with your writing. Very interesting composition and perspective. Note to self: Birkenstocks (check), Pinstripe Suite (must purchase asap) Thanks Carin.

  4. Fabulous speed tour of Chicago. That’s the way to do it, Carin … on foot (forget the bike unless it’s electric). I was very pleased to see open-toed sandals even with the pin stripes. I just have to reblog this tour …!

  5. Carin, you just made me so proud. I feel so happy that you enjoyed my home town. If I were to tell someone about my city it would never come out the same way. There is a feeling one gets when you visit this city . It is so alive and full of places to see . It has a heart beat that is hard for me to describe. You did a very good job doing just that and now I want to go home just for one more day. Someday before I get too old I would love to share some more of that city with you. Thank you for all the memories. I am touched .

    1. DeeDee, it’s true, there’s a unique energy. And so many neighbourhoods yet to discover! I know you’d be the best tour guide. Also very happy that this struck a chord. High praise from a ‘local’. (;

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