We asked our friend Carmen, student, artist, born and bred Chicagoan for the local take on her great city. Here she provides a weekend mapped out starting after you’re arrival Friday mid day. One thing universal among Chicagoans, apart from resilience to cold, is intense pride and loyalty to their city. Yet, few natives frequent touristy sites like Navy Pier or the Sears Tower (we will never give in to Willis) most commonly associated with the windy city. So Stray from Michigan Avenue for an authentic Chicago experience!
Day One: Friday Afternoon
Carmen shared some fun facts with us… Pick up a copy of The Reader, Chicago’s free, weekly alternative newspaper for popular events, concerts, films and shows. It is a Chicagoan’s bible—you can’t go wrong!
Chicago’s most well known trait is its unpredictable weather. Every season can be extreme, dictating how you may experience the city. Plan accordingly and expect to change those plans more than once.
Avoid Wrigleyville and the Redline north of Addison during Cubs games at all costs.
Chicago’s title as the “windy city” actually refers to its corrupt politics, not the weather!
Settle In: Chicago has many great hotels such as the Drake, The Four Seasons, and the Peninsula but why not stay in a boutique hotel for a more local feel? Check out Ian Schrager’s Public Chicago or the Thompson in the Gold Coast, close to all the major sights and the lakeshore. I love the Hotel Lincoln located right by Lincoln Park. It’s got a great coffee shop and rooftop bar. (A bonus: it’s right down the street from Second city, you can stumble home later.) Enjoy Richard Branson's first Virgin Hotel in downtown Chicago.
Wander: Walk or bike down Lakeshore Drive. Chicago is a unique city lined with a beach and bike path. The gorgeous views of Lake Michigan and the skyline make this a must do, regardless of the season.
Dinner: Both new and established chefs take turns heading the kitchen at Intro. Get the rotisserie duck for two at gastro pub, Duck Inn. Located in the heart of Wicker Park, Big Star offers tacos, bourbon and beer in a funky refurbished 1940s gas station. Weather permitting, sit on the outdoor patio - you’ll never want to leave! After dinner, head directly across the street to The Violet Hour. This “underground” bar has incredible cocktails and friendly staff. Be sure and leave time to walk around Wicker Park and observe the fixie bikes and beards. It is the East Village of Chicago.
Late Evening: See a show at Second City, Chicago’s well known improvisational comedy enterprise. You'll drink, eat and laugh more than you'd expect! Arrive early for good seats. Second City paved the way for a deep culture of improv, standup and sketch comedy in Chicago. The iO Theater and Up Comedy Club also offer phenomenal shows.
Day Two: Saturday
Art: Visit the Museum of Contemporary Art or for something more obscure, head south to the Hyde Park Art Center to see inventive, creative, cutting edge work. While in Hyde Park, , eat at Medici , a warm wooded tavern with delicious food and a chance to carve your name into the aged booths.
Lunch: Or head to The Heartland Cafe offering wholesome, organic food and old-hippie ambiance in Rogers Park, said to be one of the most diverse neighborhoods in America. On Wednesday nights they host an open mike night, the stage is yours if you're brave.
Afternoon Wander: Visit Pilsen, Chicago’s new hip neighborhood for dining and shopping. Plus, there is a fantastic arts scene with storefront galleries and artist studios. (Think Williamsburg before gentrification.) Pilsen, once home to Eastern European immigrants, now has a large Mexican-American community. Wander down 18th street for authentic Mexican cuisine. Then head to W. 16th St between Halsted St. and Damen Ave. to see the public art murals. These blocks of murals are organized by Art in Public Spaces, aiming to transform the neglected neighborhoods in the city. Make sure to spend some time at the National Museum of Mexican Art.
Dinner: Nightwood is an excellent choice in Pilsen, garnering rave reviews and awards offering farm to table food from it’s seasonal menu. Weather permitting, dine on the outdoor patio.
Evening: Step into the 1920s at The Green Mill Cocktail Lounge in Chicago’s Uptown neighborhood. Opened in 1907, and partly owned by Al Capone during the Prohibition era, this historic club hosts late night live jazz and poetry as well as a dance floor. Half the entertainment is watching the dedicated dancers return weekly to swing and sway. Check ahead for shows. When there's no live music at the Vic, one of Chicago's iconic music venues, it transforms into the Brew and View, showing second run movies for $5.00. The cheap beer, pizza and movie price always make for a lively crowd. For music and dancing, go to The Hideout or The Empty Bottle, both well-known music venues for alternative local music.
Day Three: Sunday
If You’re Feeling Adventurous: About a 30-45 minute drivie, in Niles, IL is King Spa & Sauna, an authentic Korean spa open 24 hours, 7 days a week. try the various nude wet and dry saunas separated by sex. You can choose between nine spa rooms that invoke “elemental therapies” such as dry heat, charcoal and stone. There is a movie room, Korean restaurant and various additional spa treatments available. It's unlike any place you’ve ever been!