Chicago Top Places

All in all, Chicago was very similar to New York but smaller. Here are my top places to go. Colours below represent locations close in proximity.

Shopping

Magnificent Mile (although touristy) is worth checking out. My favourite store was obviously Top Shop (which is a stand alone store just like New York, 830 Michigan Ave.)!

Wicker Park reminds me of the east village or the brooklyn of New York. A little more vintage and hipster there's cute shops and patio restaurants. I would just walk down N. Milwaukee Ave or if you have extra time Damen and Diversey (which we didn't get a chance to do).

Food

We didn't get a chance to do this but it's worth finding a place with traditional deep dish pizza! There's a few restaurants close to top shop.

Grand Electric is copied after a restaurant called big star (mexican food) in wicker park. Great patio and very yellow - can't miss it. There's a great brunch place called the Bongo Room - beware to make reservations or go early there's usually a line.

Nightlife

On your first night you should walk along Hubbard St. (also known as River North, C on the map below) for late dinner or bars (I would consider this their entertainment district) for young working professionals. Check our Paris for amazing food (there's also a club upstairs) or Hub 51 is you want to spend more and maybe do some celeb spotting (you never know)!

I would check out an after hours bar called Violet Hour in Wicker Park. Great decor and interesting drink choices.

Check out Drumbar Rooftop and flirt with the bouncer to get up. Apparently, there was supposed to be a party with Florence and the machine djing at lollapalooza but they didn't get their dj license in time?? The crowd reminds me of a little of the Thompson in Toronto.

For some 80's & 90's dancing I would check out The Hangge Uppe, go early to avoid the line but it moves pretty quick. Go on a Saturday remember there's 2-3 rooms with different music!

Attractions/Photo Ops
Close to N. Michigan Ave there's a mirror thing called cloud gate and close to that there's a fountain and a moving image of a person on it (kids swim here during the day and it glows at night) really cool to check out.