We all dream of visiting exciting exotic locales. My current top 10 “dream list” locations (in no particular order) are: Antarctica, Galapagos, Iceland, Azores, Alaska, Croatia, Santorini/Greek Isles; New Zealand (South Island), Bhutan. There’s countries I’ve been before that I saw very little of, and would like to spend a more leisurely time visiting, such as Australia, Japan, Nepal.
But for some of you out there, you’re dreaming of visiting the States, and Chicago is on your list for whatever reason. Maybe you fell in love with it through the movies like I did. Perhaps you like one of our sports teams, or you are a huge fan of improv comedy, you’re a serious foodie, or you love great museums.
Chicago has something for everyone, that’s for sure. So here’s ten of my favorite places around town – again, in no particular order! – and I’ll break it down into five favorite restaurants, and five favorite sites worth seeing/experiencing.
RESTAURANTS
This was a tough list, because every time I thought of a restaurant, I’d think of five more that I could easily include. So I narrowed it down to some of the places I’ve been the most frequently over the past couple years. They’re all decently priced and give you great food for your money.
- 90 Miles Cuban Café – Cuba has become a hot topic on American lips these days, but those in the know have been enjoying Cuban fare for many years. 90 Miles has a taste of the Caribbean in the heart of Chicago; they have three locations serving up fresh, tasty, amazing food. My favorite is their Bistec De Palomilla sandwich, but you can’t go wrong with a simple Cubano here, either. In addition to great food, they also host events like live jazz on Wednesdays, pig roast buffets on Thursday, and Flamenco nights! Their most public transportation-accessible location is their Logan Square location – 2540 West Armitage, a couple blocks’ walk from the Western stop on the Blue line L.
- Q BBQ – Like 90 Miles, Q BBQ also currently has three locations, although two more are in the works. Given Chicago’s history with its stockyards and the city’s intense love of meat, it’s no surprise that the barbeque business is booming all over the city, from low-key to upscale. Pick one, two, or three meats, pick your sides, and enjoy BBQ Nirvana. Big eater? Go for the Papa Q Platter. Enjoy Q’s regional sauces and influences. Q’s Lakeview location at 714 W. Diversey Pkwy. is a short stroll from the Diversey stop on the Brown and Purple L lines.
- Piece Brewery & Pizzeria – If you ever want to get two Chicagoans into a heated discussion, just bring up the subject of best pizza in town. If you want deep dish, I’ll send you to Lou Malnatti’s or the original Gino’s East. But if you want great pizza and some brewpub suds to wash it down, then head over to Wicker Park’s Piece, and get one of their New Haven-style (thin crust) pizzas. Go on game night and enjoy an enthusiastic crowd cheering on their hometown teams – Piece loves the local teams, and has designed cute Piece logos for each of them. And if that’s not cool enough for you, Cheap Trick’s Rick Nielsen is a co-owner, and yes, he’s occasionally found there. 1927 W. North Ave., Blue line L to Damen.
- Doughnut Vault – Yes, Chicago got hit with the cupcake craze and the doughnut craze. You can get heart-stopping pastries all across the city, but few induce the fan dedication of the Doughnut Vault. Their original location at 400 N. Franklin St. is barely big enough to hold a handful of people, but in the morning, the waiting line wraps around the corner of the block. (Don’t worry, the line moves fast.) They open at 8 a.m. Monday through Friday, 9:30 a.m. on the weekends, and they stay open “’til sold out” – which could be 11 a.m. or it could be 3:30 p.m. They update their stock constantly via Twitter, and you can preview the week’s rotating daily special selection on their Tumblr. Personally, I love the delicious simplicity of their “Gingerbread stack” – a threesome of cinnamon-and-sugar dusted doughnuts that taste pretty much perfect. The original location proved so popular that they added a food truck, and they opened a second location at 111 N. Canal St. (across from the Ogilvie Transportation Center) which is open 7 a.m. to 5 p.m. weekdays, and has a wider daily variety of doughnuts. Brown or Purple line L to Merchandise Mart.
- The Little Goat Diner – Chicago-born chef Stephanie Izard competed on Bravo’s Top Chef, and she not only won but was named fan favorite. Not long after that success, she opened her popular upscale Girl & The Goat in 2010. Its more casual sister restaurant, The Little Goat Diner (820 W. Randolph St.), opened in 2012, and has proven just as popular ever since. Go daring for breakfast and try This Little Piggy Went to China; and I love the Pork Belly Pancake under their “sammiches”. (Any of their sandwiches rule.) Their bakery opens at 6 a.m. and you can enjoy breakfast starting at 7 a.m.; they’re open until 10 p.m. most days; midnight on Friday and Saturday. Green or Pink line L to Morgan Station.
SIGHTS / EXPERIENCES AROUND TOWN
You already know about the obvious tourist destinations. But what else do you do after you’ve been up in the Willis or Hancock Towers, checked out your reflection in Cloud Gate (a.k.a. “The Bean”), wandered around art museums all day, and hit the tourist scene at Navy Pier? You go check out other experiences like a local, of course.
- Lillstreet Art Center – Lillstreet has been making art with the community for 40 years. If you’re local or if you have plenty of time to enjoy the city, you might want to consider one of Lillstreet’s many mulit-week art classes in disciplines like ceramics, jewelcrafting, textiles, and more. Have a little less time? Lillstreet offers some one-off classes and new full day “creative retreats”. You can support local artists by checking out their galleries and gift shop; or make a difference by having a meal or picking up a pie at their on-site café, First Slice. 4401 N. Ravenswood Ave.; Brown line to Montrose.
- United Center – The “UC’s” predecessor, the Chicago Stadium, was known as “the Madhouse on Madison”, a moniker that was originally carried over to the United Center. Chicago is a very serious sports city – and the UC is home to two well-decorated, much-beloved sports teams: the Chicago Bulls (NBA) and the Chicago Blackhawks (NHL). The Bulls were dominant in the 1990s for basketball during the Michael Jordan era; the Blackhawks have led the hockey world with three Stanley Cup titles in the past six seasons (2010, 2013, and 2015, above). With a seating capacity of nearly 21,000, the United Center is the second-largest arena in both the NBA and NHL; but standing room capacity regularly pushes their ticket sales to first. In addition to sports, the UC also hosts dozens of concerts, Disney on Ice, the circus, and other events throughout the year. CTA bus #19 UC Express or #20 Madison from the Loop to the United Center.
- The Chicago Lakefront / Lincoln Park – Chicagoans often joke that we get 4-5 months of summer and the rest is all winter, but that’s not entirely accurate. At any rate, the lakefront is never quiet; it’s the city’s backyard and its lungs – a gift to the citizens of Chicago by its master planner, Daniel H. Burnham, who insisted that “The Lakefront by right belongs to the people. Not a foot of its shores should be appropriated to the exclusion of the people.” Today, 25 of Chicago’s 29 miles of lakefront remain public parklands, studded with various athletic facilities (including a public golf course), 18.5 miles of trails, marinas, beaches, museums, picnic facilities, and more. In the summer, the city’s denizens fill the parks, and the lakefront path can be very busy between Belmont Harbor in the north down to the Museum Campus. On the east side of the Loop, you can enjoy Millennium Park, the new Maggie Daley Park (great for kids of all ages!), enjoy one of many music festivals held in Grant Park, or stroll by the harbor and Buckingham Fountain (pictured at top). At the Museum Campus, you can take enjoy the Field Museum, Adler Planetarium, and Shedd Aquarium. Take in wildlife – or a concert – at Northerly Island; enjoy a Chicago Bears (NFL) football game or other major event at Soldier Field. Wander around the shops, restaurants, theater, rides, fireworks, and city views at Navy Pier. Visit the Lincoln Zoo; enjoy the Green City Market or the Lincoln Park Conservatory. Rent a Divvy bike and go for a ride – your choices for entertainment on the waterfront are endless!
- The Improv Scene – Chicago is called “the Second City”, but they’re second-to-none when it comes to being the birthplace of the improv comedy scene. The granddaddy of them all, Second City, has produced many of the country’s leading comedians for fifty years, and you can still take classes there – or take in many shows throughout the week. But it doesn’t stop there: check out the Improv, IO Chicago, or Zanies; take in the Chicago Improv Festival; or take the stage yourself at open mike nights at smaller comedy clubs like The Playground Theater. Pick up the free weekly The Chicago Reader to find out what’s happening around town.
- The Theater Scene – Broadway in Chicago brings top musicals and shows to Chicago, as well as providing a fertile testing ground for new musicals. (Spamalot, among others, did test runs here before their Broadway debuts.) Experience world-class Shakespeare and other productions at the intimate Chicago Shakespeare Theater on Navy Pier. See well-known actors perform live in one of Steppenwolf’s powerful productions. Take in quality shows at smaller neighborhood theaters like the Raven and the North Shore Center for the Performing Arts. Like the improv scene, check out The Chicago Reader for the most current listings.
And one last wild card among my recommendations: Metropolis Coffee. You’ll need caffeine to keep you vibrant for all this fun! If you can’t make it up to their coffeehouse at 1039 W. Granville Ave. (Red line L to Granville), you’ll find their coffee on tap at various locations throughout the city, and you can buy their amazing coffee by the pound at Whole Foods.
THE WANDERBROAD 