Darlings, I just love my beautiful city of Chicago! After growing up about an hour away from ‘The Windy City’ in Kankakee by the Sea, and living parts of my life in Hawaii and California, there is nothing quite like my ‘Condo in the Sky’. Chicago is a beautiful place to visit any time of year!
Chicago in the Summer
Even I am still discovering new places to visit and explore with each stroll with my pup America! If you’re planning a trip to my city soon (or maybe you’re looking for the perfect excuse to get away!), I’m sharing my top ways to see the true Chicago, any time of year.
Places to eat around Chicago
Shanghai Terrace at the Peninsula
Shanghai Terrace at the Peninsula has been voted the best Chinese restaurant in Chicago and for good reason! It’s located in the Gold Coast neighborhood, just steps away from Michigan Avenue (a beautiful area to see if you’ve never been). It’s a great place for an elegant dinner with friends or a lover! The food is delicious and they have a great selection of wines (I recommend their Nebbiolo). I just love the romantic ambiance inside! The high ceilings, floor-to-ceiling windows, luxurious chandeliers, and an urban garden with skyline views just perfectly set the mood! My Ultimate Concierge and I love visiting when we want a relaxed but charming evening!
Gibsons Bar and Steakhouse
Gibsons Bar and Steakhouse is located in the Near North Side, and it’s been a Chicago staple since the late 80s. You’ll pass a whole array of celebrity headshots when you enter – it is truly quite the place to be! They know how to make you feel like family here – that’s for sure! Gibsons is, of course, a steakhouse through and through so don’t leave without trying the Chicago Cut! If after dinner you have room for dessert, you’ll never find cakes quite like the ones at Gibson’s (but they’re huge – 6 pounds a slice), so split them with the others at your table!
Gene and Georgetti
One of the great things about Gene and Georgetti is its location in River North. It’s not too far from the Magnificent Mile or Michigan Avenue, but it’s also a bit off-the-beaten-path, so you can take a break from all of that without feeling like you have to go home (or back to the hotel!) right away. It’s also got a wide variety of options to fit every palate! It’s an old-school Chicago steakhouse (in fact, it’s the original – starting in 1941!) They have meat, seafood & Italian specialties – so anything you’re in the mood for, you can find it right at George and Georgetti!
Experiencing Chicago Music
Located on a European-style cobblestone avenue in Rogers Park, this intimate jazz club is an artist’s haven. From cabaret to Brazilian Latin jazz, you can find talent of all kinds right at Le Piano. From small plates, global fare, and inventive cocktails – you’ll be sure to have the time of your life here.
A tour you simply must take
The Gangsters and Ghost Tour
Once you’ve had the best food and cocktails across the city, you’ll be needing an excuse to walk a bit! This tour is a great way to experience the colorful side of Chicago history, as you learn about some of the city’s most notorious gangsters and visit their hangouts. The tour starts at the Royal Sonesta Hotel on Michigan Avenue and goes through downtown Chicago, covering areas such as Chinatown, Little Italy, River North (including Magnificent Mile), Gold Coast, Lake View Cemetery (including John Dillinger’s grave), Lincoln Park Zoo and more! You will also hear about haunted places like Death Alley and hear some ghost stories along the way.
The tour includes stops at gangster hangouts like Palmer House Hotel (where Al Capone once lived), Congress Hotel & Spa (where Frank Nitti was shot by rival mobsters), and Death Alley (one of Al Capone’s favorite spots)
Bonus Chicago favorite special event if you visit around the holidays
The Christkindlmarket is a Christmas market, held at Daley Plaza in the Loop, and open just for the holiday season.
Inspired by the 16th Century Market in Nuremberg, Germany, it was one of the first outdoor markets of its kind! There are over 100 vendors offering food, arts and crafts as well as holiday gifts for sale during this time! It’s the perfect place to feel the holiday spirit and find some great gifts and stocking stuffers along the way.
Planning to visit Chicago?
Chicago is such a wonderful place to live and visit! You’ll truly never run out of things to do in this lovely city! Whether you’re planning a trip with your spouse, your best friends, your children or grands, or planning a solo trip to fill your cup and nurture your soul – you’ll always find a place to visit or thing to do that interests everyone you’re with.
Darlings, have you ever visited Chicago? If not, are you thinking about it? What has been your favorite big city to visit?
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