About Diana R
Lives in Manly, Australia
Since Feb 2014
I grew up in the northern suburbs of Chicago and lived downtown for a few years before moving to Australia to get my masters degree. I'm still here. I'm always keen for an adventure - I prefer traveling to go surf/wakeboard/snowboard/horseback ride/bungee jump/sky dive over taking traditional tours. I like to be outside as much as I can, and I love all things water related. I also like to travel to catch up with old friends. There's nothing better then seeing a good friend and sharing a home cooked meal together over a bottle or two of wine. I'm not a cook myself though, so I make sure to always be the one to bring the stories and the wine.
Historic Walking Areas
Parks, Points of Interest & Landmarks, Historic Walking Areas
Neighbourhoods, Points of Interest & Landmarks
Points of Interest & Landmarks, Architectural Buildings, Observation Decks & Towers
Comedy Clubs, Performances
Fountains, Points of Interest & Landmarks
The best way to start your trip in Chicago is with a tour down the river, learning about the history and architecture of the buildings. If the weather's nice, there's no better way to be introduced to the city! Another option is to just walk along the river and take in the grandeur of the skyscrapers along its edge — many excellent photo opportunities!
A trip to Chicago wouldn't be complete without a photo of your reflexion in 'the bean.' Head on over to Millennium park to pose with friends with a warped Chicago skyline in the background. Some of the best photos include the skyline at night, but any time of day will give you great shots!
Whenever I have friends in town, I always send them to the Art Institute because it's so much fun to explore. This fantastic art museum is open from 10.30am until 5pm, with a late night on Thursdays until 8pm. Group and self-guided tours are also available if you feel so inclined.
After a day outdoors you'll have worked up a big appetite. Head on over to Gino's East for a famous Chicago-style deep dish pizza. Gino's East is one of the best pizza places in Chicago — and believe me, I've tried them all.
If you still have energy left after a long day exploring, head on over to this dueling piano bar and sing the night away! Put in your requests for songs, or pay the pianist to stop the ones you don't like. It's guaranteed fun for everyone.
Even if you don't like to shop, you can't visit Chicago without at least taking a stroll down a couple of blocks of this famous strip. If your favorite store is usually difficult to find, odds are they do have an outpost in Chicago!
Located on the Magnificent Mile, this shopping center gives your wallet a break from all of the luxury shops lining the street. It's worth stopping by to appreciate the architecture and find your other favorites that aren't so exclusive.
If you haven't seen Chicago from above, 360 Chicago is for you! Formally called the John Hancock observatory, 360 Chicago can be accessed from the north end of the Magnificent Mile. You can buy a ticket for one visit, or for a morning plus night visit to see how the skyline changes when looking at it from 94 floors up!
One of my favorite ways to make my sides hurt: A night of laughing at the improv comedy at Second City! Snacks and alcohol are available throughout the performances, so that being said, this one is not for those traveling with kids.
One of the best aquariums in the world and open rain or shine — don't leave Chicago without spending the day exploring! You can see Nemo, sharks, seals and more, plus there are usually shows a few times throughout the day.
Visit the fountain at any point in your trip, but if you turn up at dusk there's a twenty minute water show with music and lights for you to enjoy!
Grab dinner or a few drinks at Rock Bottom Restaurant & Brewery. The portion sizes are large and the beer is delicious, so you might end up spending the whole night there if you're not careful!