Chicago, Illinois

travel
Written By Stef Caldwell

About

In my opinion, Chicago is one of the greatest cities in the US. The city is right on Lake Michigan, a fresh water lake that is so big it feels like an ocean. We have an absolutely gorgeous skyline, with an endless array of new and old buildings that touch the sky. We have all four seasons, and each makes a uniquely beautiful contribution to the energy of the city, with “Summer Time Chi” offering boating, drinking in “the Playpen,” long days on the shores of Lake Michigan, or perhaps better, in Wrigleyville, with fall and Winter offering cozy indoor options like playful arcade bars, tea rooms, gorgeous spas, culturally significant museums, fantastic shopping, and some of the best restaurants in the world. It’s a wonderful city, smaller and cleaner than NYC and LA, more condensed, and with nicer people and dare I say, better food. I’ve traveled many, many places in my life, and I always come home to Chicago.

How to get there

Chicago has two large airports O’Hare and Midway. You can fly into either. If you are traveling from within the midwest, you can arrive via Amtrak (Midwest region), Metra (Chicagoland area), or the El (it stands for Elevated Train and gets you around the various Chicago neighborhoods). If you prefer to drive, it’s easy to book your parking in advance with Spothero. For street parking, download the ParkChicago parking app in advance to save time not having to “feed the meter.”

Know before you go

Chicago is a big city with so many incredible neighborhoods. There is a ton to do all times of day and year. I always tell people the best time to come is during the summer months, simply because you get to play with Lake Michigan and the Chicago River more when you do, but truly, there is no bad time to come to Chicago. I’m keeping my recommendations for where to Stay and Eat to my favorite neighborhoods — The Loop/River North, Viagra Triangle, West Loop, and South Loop. Here’s a quick vibe-check on each of these neighborhoods:

  • The Loop/River North — This is where the large majority of companies are headquartered, so if you are in town for business, you’re probably headed to this neighborhood. The Loop is known for it’s commerce, whereas River North is known for its bustling restaurant scene, shopping scene and nightlife. If you are coming to Chicago for the first time, you can’t go wrong staying here, excellent proximity via walking or ubering to everything the city has to offer.

  • Gold Coast/Viagra Triangle — You guessed it, this neighborhood gets its name from all the mid-to-late-life people that live in the area and frequent the bars, restaurants and HIGH END stores. This is where you’ll find the fancy designer stores and the most amazing steak and lobster kinds of restaurants.

  • West Loop — This is the spot for all the foodies and techies out there. West Loop is home to Google HQ, McDonalds HQ, Fulton Market District and Randolph Street, Chicago’s best and finest chefs hail from here and an endless variety of restaurants pepper the streets from the East end (Halsted) to the West end (Ogden). This is also the east-side neighbor to where the Bulls and Hawks play.

  • South Loop — This is the neighborhood Ronnie and I called home for >10 years, so it had to make the list simply for nostalgia’s sake. This neighborhood sits south of The Loop, right on Lake Michigan, Grant Park, and Soldier Field (where the Bears play), and is the north-side neighbor to the neighborhood where the White Sox stadium.

Eat

  • Coffee — Edie’s (River North), Blue Bottle (River North), Goddess and the Grocer (The Loop, River North), and Cafe Press (South Loop) have been my go-to’s for ages. I recently popped into Good Ambler (West Loop) and loved it.

  • Smoothies — Left Coast (The Loop) is my fav, I do a custom smoothie with enough spinach to make a salad, plus almond milk, peanut butter, blackberries, blueberries and raspberries.

  • Breakfast — Hands down my favorite breakfast is brunch at Sunda (River North), you won’t find it on the menu, but order a Sumo Bloody Mary if you want a great story to tell your friends.

  • Lunch — The basic b***h in me is telling me to tell you to go to Eataly. I know that it’s not a Chicago original, but any time of year, you can walk around here and get a meal for any person in your group — from their Oyster bar, to their fresh cut meats, to their handmade pizzas and pastas, you just can’t go wrong. If you feel like getting outside instead, head to the Chicago Riverwalk and stop at any one of the many restaurants along the south side of the river for American classics.

  • Dinner — Eating your way through Chicago could take years, limiting myself to only sharing a few spots is a near impossible feat, but I will try…

  • Dessert

    • Molly’s Cupcakes has locations in South Loop, West Loop, Lincoln Park and more… Get the Blueberry Cheesecake Cupcake for mind-blowing deliciousness.

  • Drinks — Chicago is a cocktail bar haven, I attest this to all of our cold-weather months, requiring hibernation, or lots of long days at your neighborhood watering hole. Here’s where to get a few classic cocktails:

  • Dancing/Nightlife/Live Music —

    • The Loop/River North — The Bassment (Chicago’s best live music, IMO), Untitled (dancing!), Bub City (Like Nashville’s live music scene, but in Chicago).

    • Gold Coast/Viagra Triangle (you may hear this bar area referenced as “Rush and Division” the streets that intersect where the nightlife in this neighborhood happens) — The Zebra Lounge Piano Bar (tiny little bar on the ground floor of an apartment building with the best vibes), The Hangge Uppe (a Chicago cult classic, the basement is the spot for every bachelorette party ever)

    • West Loop — Lazy Bird (Live music in the basement of the Hoxton), Punchbowl Social (bowling, games and more!), Kaiser Tiger (sit outside by the fire during winter months and get your name on the list for Curling), Federales (throw your ice shot at the bell)

    • South Loop — Brando’s Speakeasy (best Karaoke Bar in the city! You’re right next to Chicago’s Columbia University, so the talent that shows up to rock out on the stage here is next-level good, with some truly awful drunk locals and travelers peppered in, the vibes are excellent)

  • Chicago Cult Classics

    • Deep Dish Pizza — LouMalnatis (their deep dish is my personal fav), Italian Fiesta (Ronnie’s fav), Gino’s East, and Pequods are all classics.

    • Chicago Dogs — Head to Portillos (River North), or for the ultimate (but slightly seedy) Chicago experience head to Maxwell Street, and pick your poison (there’s a few hot dog and polish sausage places all in a row vying for your business).

    • Popcorn — Garretts Popcorn is the iconic Chicago spot, there’s shops all around the city, you’ll smell them before you see them. Make sure to get the Chicago Classic cheese and caramel popcorn (if they have it, get the bundle which also includes Frango Chocolates).

    • Malort — Ask for a shot of Malort at any Chicago watering hole that’s worth their salt, and they’ll serve it up to ya. Make sure to take a video when you take your shot, this video is the ultimate Chicago souvenir.

Stay

  • The Loop/River North — Great for business travelers, nightlife is going to be more theater shows and the bar scene just across the river in River North, our fav hotel is the Chicago Athletic Association Hotel.

  • Gold Coast/Viagra Triangle — Great for the fashionista, you are in the heart of the nicest designer shopping in Chicago, great walkability, solid dining scene, our fav hotel is the Thompson Hotel.

  • West Loop — One of Chicago’s hottest neighborhoods, this is the spot to stay if you’re a foodie, our favorite hotel here is the Hoxton.

  • South Loop — Honestly, this is only the best neighborhood to be in if you are only in town for Bears and White Sox games. If that’s you, get an Airbnb, and make sure to order Chi Cafe when you get home and you want drunk food.

Workout

  • Gold Coast/Viagra Triangle — Rumble Boxing is where I’d head.

  • West Loop — Basecamp will help you sweat out all the extra calories you consume on Randolph St.

  • South Loop — Title Boxing for an indoor workout, get outdoors by opting for a delightfully long walk. Plug these spots into your phone to walk a big loop… Walk from Grant Park to the Shed Aquarium, then up the lakefront to the Chicago Riverwalk, down the Riverwalk to Blue Bottle for coffee and back. It’s a good 6 miles or so.

Play

During the warm months:

During the cold months:

A Dream Day

If I am packing my day absolutely full of everything that I love… Oh wow, this will be tough. My dream day in Chicago… I would wake up and head to Edie’s for a coffee, before making my way to Ritual Hot Yoga for a morning class, and to work up my appetite. Then I’d head to Left Coast to grab a smoothie, before going for my massage at Aire Ancient Baths and then back to my hotel at The Chicago Athletic Association Hotel to shower and get ready for the day. From here, I’d walk to Millennium Park to see the Bean, and through the park to Lake Michigan. Then I’d walk up the Chicago Riverwalk as far as I could on my way to Sunda for Brunch and a Sumo Bloody Mary. From here, I’d walk off my calories by heading to North Michigan Avenue and walking all the way to The Gold Coast/Viagra triangle for some shopping. Once I was done shopping, I’d head back towards the river for my boat rental (whether that was a cycle bar, a hot tub boat, a tiki boat or anything else) and to get out on the water. After getting back from the boat experience, I’d check out the Broken Shaker or Federales for some afternoon margaritas and then head to Au Cheval or Green Street Smoked Meats for some early dinner before heading to take in a comedy show at Second City. When I leave Second City, I’ll stop somewhere on the way home for a nightcap — most likely the rooftop at the London House because the views are EXCEPTIONAL. If I’m still hungry when I get home at the end of the night, you bet your bottom dollar I am ordering Loumalnatis pizza, Molly’s cupcakes, and Chi Cafe chinese food to my room so I can get a little bit of everything that I love before I go to sleep.

Summary

Chicago really is the best. When people tell me they hear bad things about Chicago, I always think they’re just talking to the wrong people. Come here any time of year and have the best time of your life. We have SOOO much to offer. I hope you find joy in trying any one (or many) of the things I’m recommending here.

Stef Caldwell https://bystefcaldwell.com
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