A Visitor’s Guide to Chicago

Chicago, IL

I recently gave some advice to a foreign friend visiting Chicago. And I’m visiting there soon! I thought it would be fun to turn it into a blog post because I’m so proud of my hometown and would love to share my two cents about what to do there. In order to keep this from getting too out of control, I limited each category to my top 10 recommendations. It was so hard. Chicago has so much to offer! Here we go…

Sights Chicago is a world class city filled to the brim with cultural experiences for every visitor. I’m the type of person who isn’t bothered doing “touristy” things in their own town. Therefore, this list is quite touristy. Take it or leave it.

  1. Visit a museum. The Chicago History Museum to dig into the city-named-after-a-wild-onion’s turbulent past. The Field Museum for its famous dinosaur skeletons. Adler Planetarium to learn more about the sun, its planets and everything else under the stars. Museum of Science and Industry for inventions that will blow your mind. And finally, the Shedd Aquarium, provided the fascinating jellyfish exhibit is still ongoing.
  2. Ponder some art. The Art Institute of Chicago has major clout. How else do you explain why they’ve had Seurat’s famous Sunday Afternoon for all these years? Try the Oriental Institute at the University of Chicago for ancient Egyptian Hieroglyphics. I used to visit it often during my art history obsession in college. As a counterbalance, go to the Museum of Contemporary Art for art that makes you wonder what the heck art is. I saw an impressive Jeff Koons exhibit there a few years back.
  3. See a show. Chicago’s theater scene varies widely. Goodman and Chicago have great shows come through. Or check out Broadway in Chicago for all the places that host, you know, Broadway shows. But then, there’s the smaller gems like Steppenwolf, Lookingglass, and the Shakespeare theaters that all have incredible, intimate performances.
  4. Have a laugh. In the mood for something light? The Second City is where Bill Murray, Dan Aykroyd, Harold Ramis, Jon Belushi, Mike Meyers, Steve Colbert, Amy Poehler, Tina Fey and many others performed before they made it big. Or try the Blue Man Group if you don’t mind getting sprayed with mushed banana. (They provide ponchos.)
  5. Listen to music. From the symphony at Lyric Opera House to the small time rock band at Schuba’s to jazz at Kingston Mines to big time festivals (ever heard of Lollapalooza?), there is something for every… ear. And if you are still not satisfied, take the train up to Highland Park’s Ravinia, where you can choose either lawn or pavillion seats, while listening to the many artists that come through. Sprawling on the lawn as the sun goes down and candles light up, drinking wine, munching on cheese, sharing pasta salad… Those concerts used to be one of my favorite summer activities.
  6. Attend a sports event. Da Bulls (or the Blackhawks) at United Center. Da Bears at Soldier Field. The Cubs at Wrigley Field. Even the Chicago Fire at Toyota Park. There is something really powerful about the Chicago sports community. The pride and the devotion of its fans are unmatched.
  7. Enjoy the outdoors. There are parks galore in this planned city, thanks to Daniel Burnham and his comrades. Lincoln Park is topped only by Central Park in NYC for the number of visitors it draws each year (according to Wikipedia anyway). Millennium Park (home of the Cloud Gate) and Grant Park (Buckingham Fountain) are other popular parks which, in my opinion, offer solid photo ops for locals and visitors alike. Case in point:

    J+J at the cloud gate

    J+J at the cloud gate

  8. Take a tour. The Architectural Boat Tour is probably the most popular and it’s easy to see why. As you cruise the Chicago River, knowledgeable guides explain all about the rather incredible history of Chicago’s buildings. Or try a Segway Tour, which doesn’t need any explanation.



  9. Walk or bike the lakefront. Just in general. It’s pretty in all seasons, but best in summer. There is a lakefront path that stretches the entire city, north to south. Now that there is Divvy, the sweet, new shared bike program, it’s easier than ever to glide through the whole darn thing. Enjoy the rollerbladers, bicyclists, joggers, volleyball-ers and, oh yeah, some really beautiful skyline views.
  10. Take in the view. Speaking of views, head to the Sears Tower Skydeck. Okay, actually I have never done this (but I plan to on my upcoming visit). I hear it is quite astounding and on a clear day, you can see Wisconsin and Indiana. Also, there is a glass ledge you can step into, suspended over 100 stories up, for the thrill-seekers out there.

Eats Food is a very important, I’d even say critical, part of Chicago culture. Just see this Chicago Food Glossary and you’ll understand. You just can’t experience this city without exploring some of the fabulous restaurants. While trying to think like a visitor, I also added some of my personal favorites.

  1. Deep dish pizzaLou Malnati’s. Best Chicago-style pizza, hands down. Seriously. Giordano’s, Uno’s and Gino’s East are all “fine”, but they don’t compare to the glory that is Lou’s butter crust.
  2. Hot dogPortillo’s. No visit to Chicago is complete without a classic, Chicago-style hot dog or a sweaty Italian beef. This is the place to get it. I actually detest the downtown location, but bite the bullet hot dog here. And don’t ask for ketchup. Never ketchup. They’ll slap your face (or should). If you really want to get fancy with your dog, scramble over Hot Doug‘s as they open. Don’t let the line around the block discourage you.

    hot doug's

    hot doug’s insanity

  3. TacoBig Star. Very trendy and you may have to wait in a (sometimes very long) line, but there is no better way to spend a sunny afternoon than by sipping margaritas and chowing down on inventive (& cheap) tacos at this hipster hangout. Note: lime juice + your skin + the sun don’t mix well. Want the cheap late night stuff? Picante.
  4. Pig face. In the mood to, you know, eat a pig’s face? How about a cod cheek? Solution: Girl and the Goat. Opened a few years ago by Top Chef winner Stephanie Izard, this creative American hotspot is completely, positively, absolutely worth the hype. (I heard her new eatery, Little Goat, is superb as well.)
  5. Seafood. GT Fish and Oyster. One of our favorite date locales. The best nights were spent sitting at the bar, downing raw oysters and dirty martinis. Another great choice is Le Colonial on Rush. 
  6. Steak. David Burke’s Primehouse. You can’t visit Chicago and not have a steak. That’s just blasphemous. I’m not really a red meat person, but David does it right. Avoid the chains. 
  7. ItalianVia Carducci. There are a million Italian restaurants in the city. What I love about this one is its neighborhood charm (now that our beloved Terragusto closed its doors). We spent many casual date nights and family birthday dinners here. The one on Division is teeny tiny, reasonably-priced and there’s never a wait. Don’t mind waiting? Rosebud on Taylor. 
  8. Sushi/Thai. Butterfly Thai. There is nothing fancy about this place, let’s get that straight. It’s a hole in the wall. But, it had to make the list, if only because they got so much of my business while I was living in Ukrainian Village (I told you this would be biased). My favorite sushi and Pad Thai, and it’s BYOB, c’mon.
  9. Sandwich. As any Chicagoan will tell you, sometimes you just need a gigantic sandwich. At Jerry’s. If you don’t get the Mindy F with peanut butter… I don’t know what to tell you.
  10. Brunch. If brunch was a sport, I’m a gold medalist. I can’t choose just one place. Milk & Honey for their huevos rancheros casserole. Toast for that pancake orgy. Nookies for any of their weekly specials. Orange for the fru-shi (fruit sushi, duh). Feast for the benedict. Rockit for the Bloody Mary bar… The list goes on.
  11. Bonus! Some places that I have never tried, but will from all the rave reviews I hear: RPM for Italian, Frontera Grill for Mexican, Sunda for sushi, Kuma’s for his famous burgers and Ruxbin for creative American.

Drinks We more or less stuck to our usual hangouts (Ola’s being one of them), but here is a variety of places depending on your mood.

  1. Beer. Head over to Goose Island Brewery (or almost any bar in the city) and get a Green Line. Really want to impress the bartender? Order the vintage Sophie or Matilda and they’ll think you’re a local. Or just someone that appreciates really good beer.
  2. Wine. Sono became a popular place for friends and I to have wine nights; it was the perfect stop after shopping binges on North Ave. They also have tasty pizzas. 404 Wine Bar (nestled in the Southport Corridor) and DOC Wine Bar (in my old stomping grounds, Lincoln Park) are also very good.
  3. ChampagneRM Champagne Salon is swanky, tiny, with French-inspired details and beautiful chandeliers. Great for dates.
  4. With a view. Duh, the Signature Lounge. Okay, I will warn you right away that this is very touristy. But, it’s on the 96th floor of the Hancock Tower and there are beautiful sweeping views of the city.
  5. Pre-dinner. I’ll always have a special place in my heart for Hunt Club because we headed there on our very first date before a meal of epic proportions at nearby Carmine’s.
  6. Post-dinnerTrump Hotel‘s Rebar or Terrace. As the name suggests, it’s a bit on the upscale side. Such great views of the river that you almost forget you paid $18 for that cocktail.
  7. Secret. Is the light on? That means Violet Hour is open. A disguised facade with a “hidden” entrance, VH has the best cocktails in the city.
  8. Sports Bar. Try Old Town Social for a sports bar that doesn’t feel like a junky college hangout. If you want a junky college hangout, go anywhere in Wrigleyville. There’s my bias again!
  9. Mobster-style. The Bedford. People around the world still remember Chicago as Al Capone’s territory, filled with mobsters, and basically a corrupt city (which it is…). This old school real bank vault turned trendy bar/restaurant celebrates that image in the best way. With stiff drinks.
  10. Late night. Innjoy. The late night dance parties can’t be beat. Although maybe I only liked this place because I could stumble home afterward. Of course, there’s also dive bar Ola’s, which hands out $1 mystery shots and has an ancient jukebox from which you can blast LaBouche. Not that I ever did that…
  11. Bonus! Need to try Maude’s Liquor Bar on Randolph (maybe before dinner at Girl and the Goat?), Hopleaf up north with it’s massive beer selection, and the Whistler because it just looks cool.

Shops Organized this category by street since there is no easy way to do this.

  1. Michigan Ave (Magnificent Mile). This is where you’ll find all the major department stores and designer boutiques. Prepare to get sucked up in the current and just go with it.
  2. Damen. Between Armitage and North are a ton of little boutiques. Old favorites include Apartment number 9 for menswear, Stitch for beautiful home goods, Riley for clothes and jewelry, etc, etc. Goddess & Grocer is a wonderful place for lunch.
  3. Armitage. Great boutique shopping (try Art Effect), with a lot of beauty stores thrown in like Kiehl’s, Benefit, MAC, and more.
  4. Southport. My Anthropologie was/still is over here, but now I’d love to also browse through Krista K and Perchance. Southport Grocery is a great place to refuel, but if you are there in the evening, Tango Sur is a dynamite Argentinian steakhouse.
  5. Division. Itty bitty boutiques abound. I loved Penelope’s for the clothing and Paperdoll for stationery.
  6. Milwaukee. The heart of what-used-to-be-hipstervile-and-now-is-yuppieville. That’s okay though. Find your Levi’s, Free People, Urban Outfitters and some interesting vintage stores here.
  7. North. I used to do some real damage on this street. With power labels like J.Crew and housewares mecca Crate & Barrel (and it’s trendy baby C2), I’d gather my necessities here. (Then grab wine at Sono.)
  8. Grand. Some of my favorite antique/junk stores are over here and they are amazzzzing. Salvage One is the best and it’s also an event venue (we considered having our wedding here, but went with this incredible space…which made this awesome list at #3)
  9. Montrose. Admittedly, I never made it up here myself. But I hear Neighborly is rad.
  10. Just trust me. The Walgreens on North & Damen. This isn’t your average drug store.

And there we have it. Now that I don’t live there anymore, I realize two things 1) how massive that city is (2.7 million residents! 234 square miles!) and 2) how little I really knew of it (I didn’t even touch on cool neighborhoods like Logan Square, Andersonville, or Pilsen). It’s amazing how you can find your little niche wherever you live and once you find that comfort, you kinda stick with it.

I know a city this large has way way wayyyy more to offer. Have something to add? Please leave a note in the comments!


{first image is from a boat tour I took with my dad back in 2010.)

P.S. My guide to visiting Amsterdam.


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