Mary K’s Guide to Chicago

 When friends visit Chicago and ask for recommendations, I stress over making sure I tell them all the best things. Maybe it’s the hospitable host in me, but I want to make sure everyone sees the typical Chicago attractions while also enjoying the city without being a total tourist. Instead of racking my brain every time and ultimately writing a novel, I’ve compiled my favorites into a blog post to help friends make the most of their Chicago visits.

The Loop

The Loop is the heart of Chicago, mainly because all of the trains make a loop so anyone from any line can access it. It’s accessible from Union Station, and it’s probably what comes to mind when you think Chicago. My main advice is to walk around. Boring? Nah. Check out Millennium Park to see the Bean, Grant Park, Maggie Daley Park, and Buckingham Fountain. During the summer, there are always festivals and free events here. If it’s cold, Chicagoans don’t care. Instead of musical festivals and yoga, we have ice skating rinks! Bundle up and if you’re around during the holiday season, check out Christkindlmarkt, the German Christmas market (please don’t fucking say Chris Kringle Market or I might start yelling at you in German, which ain’t pretty). Grab a souvenir cup of Gluhwein or hot cocoa, and enjoy the gorgeous views. Also, for the best views in the city, go to the Willis Tower SkyDeck.

Eat: Giordano’s Chicago Style Pizza

Sweat: Hardpressed is considered one of the hardest workouts in the city by all trainers, and it’s only 30 minutes. If you’re a cardio junkie, SoulCycle Loop is a must!

Drink: Cindy’s Rooftop at the Chicago Athletic Association

Michigan Avenue

The Magnificent Mile is where all visitors go to shop, even though you can go to the exact same stores anywhere else in the city without tourists. Water Tower Place is a solid mall and next door is the John Hancock Building for sky views. Again, just walking down Michigan Avenue will suffice.

Eat: If you want a Chicago “Breakfast at Tiffany’s” experience, grab some donuts from Stan’s or Do-Rite as you longingly walk past Tiffany’s on Chicago & Superior. You’ll be sure to run into some interesting characters along the way. Also, check out Eataly for a unique Italian experience. It’s part market, part restaurant, part cafes.

Sweat: Not quite Michigan Avenue, but Barry’s Bootcamp for the most glamorous sprint + lift sweat. Or, check if Nike Training Club has any classes at the studio while you’re in town. They’re free!

Drink: Don’t go out on Michigan Avenue. It’s inundated with tourists.

The Lake

The gorgeous lake is my favorite part of the city! Walk, run, bike, rollerblade, or move however you choose. Key points along the lake are Navy Pier (ya, you can go there for any tourist-y delight but you don’t need this blog post to tell you that), Museum Campus, North Avenue Beach (where I take all of my “cool pics” — thanks for asking!), Montrose Harbor, and Northerly Island. Enjoy!

River North

River North is my favorite neighborhood to work and play. It’s got the same hype as Michigan Avenue, but on a weekend morning, it’s quiet with people in Lululemon getting their Whole Foods fix. Explore the River Walk and check out the Merchandise Mart. I work on the 13th floor at 1871, but this building is large enough it needs its own zip code!

Eat: Meli’s Cafe for brunch. You’re welcome. Portillo’s for any other meal to get your infamous Chicago dog or other greasy sandwich (don’t forget the chocolate cake shake!). For a fancy dinner out, check out RPM Steak.

Sweat: ENRGi Fitness to see me or any of the other awesome trainers, duh 😉

Drink: Hubbard Street is the place to be! Bottled Blonde, Joy District, Bub City, Three Dots and a Dash… see more on this post here!

Lincoln Park

I live in Lincoln Park, at the intersection between young, picture perfect families and ratchet DePaul students. Armitage Avenue is the cutest to explore and window shop. You have to check out Lincoln Park Zoo! Not only is it free, but it’s also not just about confined animals. During the Christmas season, Zoo Lights is the place to be.

Eat: Jeni’s Ice Cream and Glazed & Infused Donuts! Oh, real food? Homeslice Pizza, Cafe Ba-Ba-Reeba, or Blue Door Farm Stand

Sweat: AIR Aerial Fitness or Pilates ProWorks

Drink: J. Parker for the rooftop view, or for a wild night out, start at Lion Head Pub before making your way upstairs to the Apartment


If you’re at all a baseball or Cubs fan, you have to check out the stadium. Since winning the 2016 World Series, the area is a lot nicer and fun to explore. Even if you don’t make it into a game or an event at Wrigley Field, it’s a cool neighborhood to explore. At night, prepared to drank.

Eat: Uncommon Ground is a unique restaurant that’s hella organic. Otherwise, literally anywhere will sell typical sports bar food.

Sweat: Sometimes they offer free workouts at the Park at Wrigley!

Drink: Deuces and the Diamond Club, Irish Oak, but definitely Old Crow. You can’t go wrong, and you won’t remember anyway.

West Loop

West Loop is often claimed to be the best Loop, and I can’t deny it. For more of a local, gentrified charm, explore the West Loop where you’ll find lots of foodies and murals.

Eat: Au Cheval burgers are worth the wait, Green Street Smoked Meats, or check out the Allis of Soho House for bougie brunch.

Sweat: Brooklyn Boulders is a massive facility for rock climbing

Drink: Get a tequila ice shot at Federales and then throw it at the bell. Just do it.

Old Town

You can read more about Old Town in my nightlife post, but it is a super cute area if you make it a little more north than Michigan Avenue.

Eat: Happy Camper pizza, or Kanela Breakfast Club — monkey bread is a must!

Sweat: There’s another SoulCycle here, and there’s also Runner’s High, which is the SoulCycle for runners

Drink: Benchmark, Fireplace Inn, Pour House

Wicker Park

Ahh, hipster territory. It’s a great place for foodies like West Loop, but a little more grungy. I’ll be waiting for a Wicker friend to call me out on this hahaha

Eat: Furious Spoon, Antique Taco, Bongo Room, or Big Star

Sweat: Training Revolution, or explore the 606!

Drink: The Robey for a rooftop drink, or Mahalo for an insta-worthy Hawaiian drink

Don’t forget to check out my post on Chicago’s nightlife! Let me know if you’re visiting —  hope ya enjoy Chicago!

++ Mary K

2 thoughts on “Mary K’s Guide to Chicago”

  1. This is amazing. Thank you!!!

    Jillian Jernas

    University of Central Florida Marketing ’19

    UCF Rowing | UCF CHAARG

    Cell: 419-346-8817



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