Weekender Series – Chicago

Chi-Town, The Windy City, The Second City, whichever moniker you choose for Chicago it’s just wonderful.  I’m a New Yorker at heart but Chicago is cleaner and friendlier, albeit quite a bit colder! I’ve been a few times to Chicago, always for events and have done my fair share of exploring this incredible city.

Where to Stay –

I prefer to be in the middle of the action as a home base when I travel.  Most recently I stayed at The James, which was renovated earlier this year.  We had 4 to a room with 2 queen beds and still had plenty of space for all of our belongings without feeling like we were on top of each other.  The beds are also REALLY comfortable and the restaurant/ bar in the lobby is great.  The first time I visited I stayed at The Hard Rock on Michigan Ave and loved it.  Its a typical Hard Rock but I went to every floor to explore what memorabilia was around and whose pictures were on the wall.  However, if you prefer an elevated experience I suggest The Peninsula.  The staff is so welcoming, the area is very sleek and there are great dining options available, like Pierrot Gourmet, where I highly recommend the Alsatian Tart Flambée.

Where to Imbibe & Dine –

The food options in Chicago are endless but I’m going to give you a few of my favorites!  If you’ve never been to Eataly, or you are staying at The James, I would recommend popping in at least for a Nutella Crepe & Cappucino in the morning.  I could spend hours in Eataly, but I have one here in New York.  Its right next to The James (as is a Shake Shack!) so its really easy for a quick bite.  

Chicago Deep Dish vs. New York Pizza… the age old debate. There are a ton of places to try the deep dish pizza, and I’ve eaten my way through a few of them.  My favorite though, is Giordano’s.  I overdid it with cheese sticks before the pizza, but it was a go big or go home kind of situation.  I just love biting into that pie of cheesy, gooey, sinfulness.  Seriously though, I would get on a plane right now just to have that if I could.

Cafe Ba Ba Reeba! is a tapas restaurant in Lincoln Park that is both aesthetically pleasing and delicious.  I would recommend trying the Mezcal Mule and traditional Sangria for drinks, while dining on Pinxtos Platter, Burrata with Catalan Tomato Bread, Spanish Olives, and Rioja Braised Short Rib. The area here is really cute so I would recommend walking around after dinner for a little exploring. 

For some nightlife I suggest making your way over to The Beauty Bar.  The decor is made to look like a 1950s beauty parlor with teal interiors and a disco ball in the back!  There was a bit of a line when we arrived and it was pretty crowded but the music was great and every seemed to be having a great time.  I will 100% be back here on my next trip. 

What to Do-

There is so much to do in Chicago but here are a few of my favorites in relation to The Sporty Sommelier. Wrigleyville is a MUST.  Even if you don’t actually head to a game, you should walk around the area.  There are statues featuring Chicago Cubs legends such as Harry Caray, venues for music and other entertainment, as well as a ton of bars. Pretty much any kind of vibe you could want down Clark St.

Shopping is great in Chicago. You can find literally anything you want but my favorite store is the Bloomingdale’s Home Store.  Its actually built to resemble an Islamic temple so pay attention to the detail when you walk around.  Most of the store employees should be able to give you the history of the building. The selection of home goods though was unlike I had ever seen.  I just walked around in amazement for about 2 hours, somehow managing not to buy anything although I’m sure it was due to lack of space available in my suitcase (something I do on purpose).

Navy Pier is touristy but worth checking out.  There’s a movie theatre, beer garden, museum, ferris wheel, shopping, entertainment, and dining all on the pier.  Personally, I love Margaritaville, but there are some non-chain options on the pier as well as fast casual dining.

Soldier Field is another great place.  I came a few years ago for a Panthers – Bears game and had the best time.  Its a really beautiful walk from downtown to the stadium, check out Buckingham Fountain, or you can take a water taxi from Navy Pier.  Take advantage of your location and wash down that Chicago Dog from First Down Franks with a Goose Island.

I most recently was here to see Norah Jones at The Chicago Theatre.  I’m a big theatre person, I go to see Broadway shows as often as possible so getting to see such a historic theatre was really cool for me.  Its got a very European feel to it, with an Arc de Triomphe-esque arch out front, and the interiors are covered in murals and gilded decorations.  If there’s someone on tour you’d like to see and they are playing here I would definitely recommend scheduling a trip around it!

Last but certainly not least is a ride down the Chicago River with Wendella.  It is an absolute must for going to Chicago.  I’ve done it every time I’ve been and I love it, plus there is a bar on board.  My favorite part is when you get out to Lake Michigan and can look back to see the whole city shining back at you in all its glory.

Chicago is one of those cities that you always want to go back to.  Its easily accessible, not overly priced, and really features something for everyone!

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