The Angeleno Guide To Acing A Quick Trip to Chicago

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The Angeleno Guide To Acing A Quick Trip to Chicago




So much to do, so little time. Story of our lives. Chicago is an incredible destination with so much to see and experience, but when you’re ‘just visiting’ it’s nearly impossible to nail down what seems most important to get done – especially when you’re short on time. I spent three glorious days in the Windy City last week and packed in as much fun (and most importantly: food) as possible and if there’s one thing I’ve learned, a plan of attack is kind of a good idea. I don’t want you to feel lost, confused, or disappointed, and while I can’t call myself a Chicago-pro quite yet, I’ve got friends who are and have directed me to some of the city’s best. (Ieena and Riya I’m looking at you!) Follow this here quick guide to the city and fear not one shred of disappointment during your travels! Angelenos and fellow Chicago-curious people… I gotchu covered.



I’m personally a lover of smaller boutique hotels. If you’ve got the means to drop $900 – $1300 a night on a room, the Peninsula is pretty top notch but those of you looking to spend more on your entertainment might want to consider spots like Public Hotel, Acme, The James, or where I stayed – MileNorth. The River North area is a prime location to be for walking, shopping, and dining, so make it easy on yourself and pick something around this central location.





I’m only speaking from experience but the perk to dollar ratio at MileNorth was outstanding. They had the best room rates, the perfect location right next to Magnificent Mile, the largest rooms (which I’ve heard is hard to come by), a rooftop bar, and a coffee shop/bar in the lobby. AND excellent taste in decor – crucial. I loved staying here and would do it all over again!



There are an insane amount of great restaurants in Chi-Town, many of which people wait hours to get tables at, and hey if you’re in to waiting, you do you! But if you’re only in town for a limited amount of time, perhaps famed favorites like Au Cheval and Girl and the Goat just aren’t happening this trip. Good news is though that there are plenty more options to choose from that are all just as tasty and just as noteworthy.




The Purple Pig

“Cheese, swine, and wine.” Need I say more? Besides being masters of cheese and charcuterie, the Purple Pig offers an incredible and surprisingly beautifully crafted menu of fantastic small plates guaranteed to please. Look at this photo above. Talk about the art of plating? That’s only twelve-freakin-dollar burrata! Ugh, so good it actually hurts my feelings.

Order: the Greek cornbread, The Pig Platter (because why not), the octopus (either dish), and the meatballs.






When you need a break from all the deep dish pizza, Sunda is the perfect destination for some delicious light “New Asian” fair. But like, some of the best (or only?) “New Asian” fair you’ll ever have – just to clarify. Did I mention it’s a “Michelin recommended concept”? NBD. The place is continually packed night after night and if you don’t have a reservation don’t fret, they’ve got plenty of sushi bar and communal seating to around!

Order: Steamed Pork Belly Buns***, Shitake Edamame Dumplings, Signature Spicy Tuna Crispy Rice, Crazy Rice, and one of their amazing and incredibly inventive sushi rolls.




Bar Siena

Only having opened as of a few months ago, Bar Siena is decidedly the more casual and trendy than sister Siena Tavern, but appears to fit in quite well amongst the rest of their Randolph St neighbors such as Au Cheval and Girl and the Goat. With two stories of seating, an epic bar, rustic decor, incredible pizzas/calzones/bomboloni crafted by the incredibly talented (and unfortunately attractive) Chef Fabio Vivani, what more could you ask for?

Order: Fireball Pepperoni Pizza, Meatball Sandwich, Grilled Octopus and Shishito Peppers, and something sweet from the BOMBOBAR!



What do you do when it’s cold and sad out? You drink. Chicago is chilly 300 out of 365 days a year – or so it would appear – so going out for drinks is a regular activity. The supply and demand are in perfect balance and whether you choose to kick it old school or go with a trendy new concept, Chicago knows a thing or two about helping those in need get their drink on.



Three Dots and a Dash

Have you ever sipped on a cocktail in a skeleton glass? What about a seahorse? A tiki? Well if you’ve always wanted to, and you wanted to do it at one of the best tiki bars on the planet, Three Dots is an absolute must. From the blue skull alley way entrance to the fantastically adorned THIRTEEN DOLLAR cocktails, prepare to have your mind blown. Grass skirts and coconut bras optional.



Gilt Bar

Mid-price, high-style, and totally “Chicago”, Gilt Bar is another recent bar/restaurant concept well worth making a pit stop somewhere along your evening journey through town. Come by for the wine and basement seating, but stay for the brussel sprouts, the burrata and toast, and most importantly the desserts.




If you’re a lover of hotel bars, especially the ones with sweeping views, then Rebar at the Trump Hotel is a must. It may fall on the “bougie” end of the hotel bar spectrum, but this is one hotel bar who’s insane front row views of the river below make the prices on beverages completely worth while. Even on a busy weekend night you’ve got a pretty good chance of snagging a window seat, so come by at sunset, grab a drink, and enjoy.


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[photos via]


Known for being an old school restaurant and an all around class-act joint, Gibson’s is a Chicago institution. Everyone who is “anyone” that has been to Chicago has visited Gibson’s and it really is no wonder – from the staff to the food, the place is fantastic, but the bar is the perfect place to get a sense of the vibe without having to drop a few coins on dinner. The Sinatra tunes, white napkins, old school bartenders and fellow patrons though? Priceless. 



You can always go the obvious route and go see Cloud Gate (aka:”The Bean”) or go 103 floors up to stand at the top of the Willis Tower (aka: Sears Tower) Sky Deck – I won’t stop you. But with so many other cool and unique things about Chicago it’s important to remember to consider all of your options. Personally I like to maximize my time for the effort by going to places I know offer food and booze as well as history and culture. If you identify, please consider the following.




Cheeses, sweet treats, and carbs OH MY! Eataly Chicago is your one stop shop for all things culinary. Whether that means you’re doing the cooking or they are, they’ve got you completely covered in the cookbook, kitchen accoutrement, and prepared *Italian* food departments and it’s a total blast to walk through this two story foodie haven.



Architecture Boat Tour

Where else in the US are you going to take an architecture boat tour, so what the heck, why not. In just 90 minutes you’ll see and learn about over 50 of Chicago’s most famous structures, all the while riding comfortably down the gorgeous green river running straight through the city.




Looking to bar hop with friends and check out Chicago’s historic Wrigley Field while you’re at it? Head to Wrigleyville. I happened to be visiting this sports-centric area during the NLCS and while it’s a lot of fun to be there while baseball games are in play, the area has character regardless of what’s going on at the ball park. It’s admittedly a little dirty and a little seedy, but still a lot of fun.



Shopping on Magnificent Mile

SO. MUCH. SHOPPING. Whether it’s small boutiques, department stores, Zara, Topshop, or Chanel you seek, Magnificent Mile has it all. Never have I ever seen so much shopping in one place. Enter at your own risk.


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