It’s been a while since I visited this beautiful city and admired this view from the top of the Sky Deck, and it was definitely long before I started travel blogging, but it’s a city I thoroughly enjoyed visiting and somewhere I’d definitely visit again – hopefully in the summer, and it would be a dream to drive Route 66 from here – there is a sign that still marks the original start point of Route 66 that’s still standing…
Here’s my top N I N E..
Green Mill Jazz Lounge: The Green Mill was originally a dance and music venue, similar to Paris’ Moulin Rouge. During prohibition is was a speak easy and a favorite hangout of Al Capone. It is also believed to be the oldest continuously run jazz club in the United States, and it serves yummy cocktails that you can sip from a booth that makes you feel as if you’ve gone back in time…
The Skydeck at Willis Tower: Now this is also one hell of a view, and not quite the relaxing experience you get at Trump Tower, but seize the opportunity to have a view that spans as far as four states on a clear day from “the ledge” *cue Matt’s terrible jokes about him being the only ledge in the building* and then you see that not the case… the Ledge’s glass boxes extend out over 4 feet from the Skydeck over the streets of Chicago at 1,353 ft – an experience not to be missed!
Rockit Burger: The best burger I will ever eat by a long stretch, that is all I need to say – aside from the fact I’ve had dreams about these burgers ever since they’re so damn good!
Chicago Deep Pan Pizza: When in Rome and all that… you must try what’s tradition right?! Rumour has it Lou Malnati’s and Gino’s East serve up some of the best slices in town.
Cloud Gate: Walk all around Grant Park and you’ll come across many sculptures and works of art in this haven within the city (think Chicago’s equivalent to Central Park), but then you’ll come across Cloud Gate and it had to be my most favourite structure of all – make sure you get the obligatory tourist selfie in its reflection!
Rooftop Bar in Trump Tower: If not for the views alone, oh and the wine – it’s a must visit!
Wrigley Park: Visit this baseball field to catch a game of the Chicago Cubs the ground ground is old school, having been built in 1914 and what an experience!
Chicago Theatre: You know the one you see in all the photos, if you can get tickets to see something, at very least just walk past it and get a shot of C H I C A G O in lights…
Shopping: It really is amazing so don’t miss the opportunity and build some time for it into your trip – I still have ROMO (reality of missing out about that one dress I should’ve but didn’t buy)!