city guide | chicago

Disclaimer: I was born and raised in Chicago, have spent over twenty years in this city, and there are still a million places on my To See, To Do, and--of course--To Eat lists. This guide just barely scratches the surface of what the city has to offer, and my best advice is to simply explore on your own and see what you happen to stumble across. (One of my favorite personal discoveries? The U.S. Air Guitar Championship. True story.)  Still, here's a tiny peek into what you'll find in The Windy City...

For Foodies:

Portillo's (Multiple Locations) - What we're known for. Meat lovers will fall head over heels for the Italian beef sandwiches and famous Chicago hot dogs... Not a meat person? Don't worry: the cheese fries are equally to-die-for. Oh, and did I mention the chocolate cake shake? Yes. You heard me. Chocolate. Cake. Shake.

Lou Malnati's Pizzeria (Multiple Locations) - World famous Chicago-style deep dish. Legit.

Greek Islands (River West/Greektown) - A classic Greek restaurant in the middle of a neighborhood that's full of Greek restaurants. Hence, you know, "Greektown." The menu is huge and I've never had an item I didn't love--there truly is something for everyone. And the flaming saganaki cheese? I'm allergic to cheese and I still eat it... yep. That good.

Garrett's Popcorn (Multiple Locations) - It's one of Oprah's Favorite Things. Need I say more?

XOCO (Near North) - This Mexican cafe, inspired by street food, is part of the Frontera Restaurant group from Chef Rick Bayless. Delicious tortas, melt-in-your-mouth churros, and rich Mexican hot chocolate. Sit outside, people watch, and eat up. You won't be disappointed.


The Goddess & The Grocer (Multiple Locations) - Best. Deli. Ever. Great salads, great sandwiches, and all the finest, freshest ingredients. And the matzo ball soup... Well, let's just say that they know be my name there--and it's all because of that soup.

Hub51 (River North) - Trendy, tasty, and you may or may not run into a celebrity.

Sweet Mandy B's (Lincoln Park) - Buttercream frosting, cookies, cupcakes, and decadent desserts that you never even knew existed. Good luck leaving with anything less than ten dollars worth of sweets and one serious, serious sugar high.

For Touristy Tourists:

The John Hancock Building (The Loop) - It's true that the Sears--okay, "Willis"--Tower is more famous, but I've always preferred the view from the top of the Hancock Building. Stunning. Plus, it's always fun to stop for drinks at the Signature Lounge on the 95th floor... Bonus: There are floor-to-ceiling windows, so be sure to visit at sunset.

Michigan Avenue (The Loop) - Check out "The Magnificent Mile" if you love to shop. You'll find everything from H&M to Nordstrom to all the high-end designers on Oak Street. There's also some of the city's best architecture (love the Wrigley Building), rich history, and a slew of upscale steakhouses. Oh, and if you visit in the spring, all the tulip beds look absolutely breathtaking. Good views and good shopping--what more could you ask for?

If you're a fan of museums, well, we have plenty. The Field Museum, The Museum of Science & Industry, Adler Planetarium, Shedd Aquarium, and on and on. My advice? Research the exhibits, map out your day(s), and buy tickets ahead of time if possible.

For Sport-o's:

Soldier Field, Wrigley Field, US Cellular, and the United Center--the Bears, the Cubs, the Sox, the Bulls and the Blackhawks. Even if you're not a fan, a game at any of these stadiums is a guaranteed good time. And Wrigley, it's basically a historical landmark... a historical landmark surrounded by all of the best bars and beer gardens. Like I said: A guaranteed good time.

For Movers & Shakers:

Chicago is a remarkably walkable city, so my first suggestion is just to walk whenever and wherever you can. For those of you who like to wander (or run), the best place to be is along the lakefront: You can walk, run, bike, or rollerblade for miles and miles along Lake Michigan, and the views of the skyline are spectacular.

Grant Park/Millenium Park is another great location for exercise. While you're there, visit the famous metallic bean sculpture or try to catch a free concert at the Pavilion. 

For Artsy Folk:

The famous Art Institute is a Must Do--and if you have time, I highly recommend the Museum of Contemporary Art, too. Love musicals? Check out Broadway in Chicago to see which shows are in town during your stay. (You'll find your best pre-play dinner at Petterino's Restaurant in the Theatre District. Order the peppermint ice cream.) 

For a more affordable option, look into the productions at the Chicago Shakespeare Theatre on Navy Pier--and, if the season's right, you can ride the Ferris wheel during the fireworks later that night.

For Pop Culture Nerds:

Are you a Saturday Night Live fan? Then you have to squeeze in time to visit Second City, the improv theatre where so many of the SNL greats got their start--Chris Farley, Mike Myers, the Belushi brothers, Tina Fey, Steve Carrell, Stephen Colbert, and Bill Murray, to name a few. Tickets are affordable and I promise you will love whatever show you see.

For Hipsters:

The Bucktown and Wicker Park neighborhoods are basically a hipster heaven--kitschy thrift stores, record shops, hole-in-the-wall restaurants that use all the best local ingredients, and used bookstores galore. Not to mention all the great bars and concert venues. Bottom line? It's one of my favorite areas to explore during the day and also one of my favorite spots when I go out at night. It's a win-win.

For Happy Hour Aficionados:

Big Star (Bucktown/Wicker Park) - A casual, rustic chic sort of atmosphere and simple, tasty organic food. (To go along with great drink deals, of course.) Absolutely love this place.


The Gage (The Loop) - A pricy choice, but well worth it if you're looking for a cozy, upscale vibe. Steps away from Millenium Park, the restaurant/tavern has vintage decor, great drinks, and amazing food... you really can't go wrong here.

Seasonal Picks:

Fall

Okay, I'm biased... but seriously, even if you're not a diehard football fan, you should at least hit up a pub or a sports bar in the city on game day. Chicago comes alive whenever Da Bears are playing, and the people on the streets can be even more entertaining than the game itself! A good bet? The stretch of bars on Lincoln Avenue between Belden and Webster in Lincoln Park--Halligans, Wise Fools, Lionshead Pub, etc. Oh, but do yourself a favor: If we're playing the Packers, don't root for them. 

Winter

If you're visiting during the holiday season, you should most definitely visit the Christkindlmarket, a traditional German market that sets up on the Daley Plaza at Washington and Dearborn. Not only are there some seriously amazing food stands, but there's also some fun vendors who sell German trinkets and art prints and random little knick knacks you won't find anywhere else. Afterward, you can hop on over to Millenium Park to ice skate beneath the skyline! 

Spring

Weather permitting, the Chicago Architecture Boat Tour is an absolute Must. It's a great way to see the city--a boat tour along the Chicago River that passes right through the heart of the city and shows off all the most beautiful, impressive buildings. (Also a great way to get a tan on a sunny day... Just saying.)

Summer

First on the summer to-do list? A baseball game! (Preferably the Cubs--not just because I'm a fan, but also because you can spend the day gallivanting around Wrigleyville, ducking into all the trendy boutiques/pubs along the way.) If you visit in July, the Taste of Chicago will blow you away: all of the city's best restaurants sell their signature dishes for a lower price... Such a steal. If it's especially hot, head over to Oak Street Beach and cool off beneath the imported palm trees. (Yep. That's right.)


Hopefully this little guide gives you a few ideas for any trips you may be taking to Chicago!
And, as always, feel free to email me for any specific questions :)

(Photo: My Flickr)