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Where To Eat, Stay and Play in Chicago

11/13/2014 02:40 EST | Updated 01/13/2015 05:59 EST

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The exploration of Chicago requires a good pair of shoes and a good few days a couple of times a year, ideally. On the weekend that I visited, I had every experience from watching Nick Walenda brave the high wire in high winds with a blindfold to deep dish pizza that gave my mouth such pleasure and my guts such strife. Toronto Island to Midway and on the Orange line train to the downtown LOOP took less than $300 and 3 hours. Here are the highlights:

Stay choices:

Top Notch

Fairmont Gold club

$435+ per night. Includes a spacious room and access to the club lounge with excellent breakfast, cocktail hour appetizers and concierge business services. No need was left un-noticed nor unattended.

Best view

Swiss Hotel

$263+ per night

This triangular, Harry Weese architectural building maximizes the property shape while providing stunning views of the lake, Navy Pier and the Chicago River. Some corner rooms provide all three.

Magnificent Mile with rooftop hot spot

Urban and New

Mile North

$275+ per night is a relative newcomer to the scene. It is an urban, hip place with a nifty rooftop bar providing views southward along the lighted path.

Play Choices:

House of Blues: Gospel Brunch

Who wants to go to church on Sunday when you can eat chicken and waffles while waving your arms in the air with a "hallelujah!" on your lips and a full on gospel choir? In this iconic, gorgeous theatre hosts gospel concerts with a whopping buffet on the side.

Buddy Guy's Legends

Legendary Chicago Blues man has a hot spot in the Loop in downtown Chi-town that just must not be missed. Practically any time of the day you can find some version of blues. On the night I went, an acoustic duo crooned, a bluesy rock band ripped and a funky rhythm band with horns got me up on my feet. The cover charge of $20 kicked in a 9 pm but the sitting at a table, chatting with locals, drinking Buddy's brew lasted for 6 hours.

Field Museum

Classic history and architecture, the Field's museum sits at the bottom end of Millenium Park. The special shows include a Haitian Voudou exhibit that was authentic and moving. Plan to spend at least half a day here exploring everything from dinosaurs to mummies

Architectural Boat Tour

Chicago is a river town so it must be explored from the water. There are a few "architectural" boat tours but only one is run by the actual Architectural Foundation with docents providing history and context. The kiosk is at the foot of Wacker and Michigan Ave. Well worth the $40.

Nordstrum's Rack/Macys

Ask any woman. There is nothing like a clearance rack at either one of these places. It is hit or miss and you have to love the thrill of the hunt but it is well worth the investment of a couple of hours. Let's just say "5 pairs of top quality shoes for $200" and call it our little secret.

Weigh choices:

Ok, it isn't all about healthy food on vacation. It is kind of about exploring what that region has to offer and then walking it off so it doesn't weigh you down.

Aria: Superior Sushi

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Housed inside the Fairmont Hotel just steps from Millenium Park is a superior sushi spot. Lucky for us, it is eclectic enough to convince raw fish hating foodie friends (oxymoron? Maybe) to join. The naan bread is crisp, chewy and filling when it comes with a series of housemade dips from mango chutney to spinach puree.

Lou Malnatis

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Chicago-ites don't really eat deep dish pizza but when they do...it is here. You probably only need 2 mouthfuls of the classic to feel full but be prepared to eat celery the rest of the day(or week) because you won't be able to stop. Interestingly, there is a tab on the website for nutrition info but it is not operational.

Shaw's Crab House

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The find! A tweep suggested this spot while I was and all recommendations from social spheres must be followed up. What a gem! The decor of this sprawling 1920's is broken into cozy rooms. One with an open kitchen and soda bar that is as cozy as it is splashy. Fresh and excellent seafood is the highlight here. Come hungry.

If you haven't been to Chicago, you really must, it is a baby New York with efficiency, community and space. The food is cheaper but better quality and the heartbeat is a blues rhythm rather than a frenetic hum.

Note: some experiences were hosted, others paid for out of pocket but never fear, my opinion isn't for purchase, I only share what I love.