With an incomparable culinary and cultural scene, grandiose architecture, and beautifully manicured park lawns, there’s not much the Windy City lacks in terms of excitement. So in a city where boredom ceases to exist, where is a one expected to begin? Lucky for you, we’ve taken the stress out of planning your next Chi-town excursion with a list of our own must-see neighborhoods, shops, eateries and happenings. Experience them at your own enjoyment.
Hot Hoods To Visit
A mini-guide to Chicago's most popular areas.
This area of Chi-town attracts millions of tourists each year for its endless shops, attractions and restaurants that form a loop (pun intended) around downtown Chicago. Considered the business district of Chicago, with all of the hustle, bustle and skyscrapers (we suggest a boat tour), the Loop manages to find balance with the lush green lawns of Grant Park and Millennium Park, just steps apart from one another. The Chicago Symphony Orchestra, Art Institute of Chicago, Joffrey Ballet and annual Taste of Chicago are just a few wonderful attractions to enjoy in the bustling neighborhood.
Near North Side
The Near North Side, made up of the Gold Coast, Streeterville and River North neighborhoods, is considered one of the wealthiest and ritziest areas of the city – making it the touristiest as well. The gorgeous buildings, apartments and condos along Lakeshore drive make it a great walk-around neighborhood. The Navy Pier, the number one tourist stop in Chicago is home to plenty of shops and restaurants. Magnificent Mile (which runs down Michigan Ave.) is home to endless retail stores ranging from chain stores to high-end designers. If you’re in the mood for something less bustling, head to the Museum of Contemporary Art to check out a few exhibits.
The trendy neighborhood of Bucktown offers the best of both worlds for Chicagoans. Located near Wicker Park and the Loop, the area is a central location for folks searching for easy access to downtown, but the slower pace of the burbs. A stroll down Damen Avenue will have you forgetting you’re in suburbia with stores like Bebe, Arden B., Marc Jacobs and some of the city’s best thrift stores and one-of-a-kind boutiques. If you get hungry, you’re in luck. The area is filled with eclectic eateries, cafes and pubs to satisfy your thirst and huger.
This neighborhood has seen some drastic change over the years. The once crime ridden community now attracts a young and vibrant crowd (thanks gentrification) and is considered one of Chicago’s most ethnically diverse ‘hoods. There is no shortage of delicious Mexican food thanks to the large Latin population and the Farmer’s Market is a favorite among locals. The relatively close distance from downtown makes it ideal real estate for young professionals.
Lakeview: Home to Wrigley Field, the Lakeview neighborhood attracts plenty of sports fans, shopaholics and tourists alike, year round. The community is offers great mix of residents making all who visit feel welcome. After Wrigley Field, the most talked about destination is Boystown, where a large population of Chicago’s gay community resides and where the annual Gay Pride Parade takes place. There are plenty of bars and nightclubs in the area – both gay and straight – that are perfect for dancing the night away.
The Lincoln Park area of Chicago is one of the more sought after residential areas of the city. The massive green lawns that make up Lincoln Park run all along the city’s lakefront, giving residents and tourists breathtaking waterfront views and easy beach access. Inside the park, locals can perfect their backhand on the open tennis courts or test out their 9 iron on the manicured golf course. Don’t miss a stroll through the Lincoln Park Conservatory or the Lincoln Park Zoo.
Bavette’s Bar & Boeuf functions as a steakhouse suitable for schmoozing over business dinners, nestled in a giant leather booth while drinking martinis, noshing on rib eye and listening to the sounds of jazz. But there’s also a dark basement area filled with the sounds of fast music booming-bass pumping, a paradox in the same River North location brought to us by well-known restaurateur Brendan Sodikoff, whose trademarks include leather couches, distressed brick and sepia-toned lighting. 218 W. Kinzie St. 312-624-8154
For two weeks, the best films from around the world will be on display at Chicago’s AMC River East 21 Theater for the 48th annual Chicago International Film Festival. 150 films from 50 counties will be presented by first-time directors and legendary filmmakers alike. Panel discussions are expected to take place, along with plenty of star sightings. For ticket information, be sure to visit the film festival’s official website.
You won't find preening, trendy old-timeyness here, just authentic 18th-Century-referencing and decidedly masculine charms: gas lanterns, black Windsor chairs, a thirty-foot walnut bar and a coal bucket fireplace. Former Sepia chef, Kendal Duque, straddles tradition and innovation; indeed, where else might you sample such glories as sunchoke velvet soup with braised oxtail and marrow dumpling, or fish and shellfish pie with fennel, lobster-sherry sauce and potato crust? A beer selection just shy of a hundred should keep the punters coming back again and again. 1416 S. Michigan Ave. 312-786-1401
For one night only, you’ll have the opportunity to be moved and inspired by breathtaking images at DIGNITY Chicago’s photography exhibition, fair and auction benefiting the non-profit organization Acumen Fund. The event will showcase photographs for auction by renowned and emerging artists taken in regions where Acumen Fund is tackling poverty. Savory nosh will be provided along with beer, wine and cocktails and an open bar. Guests will also be treated to a performance from talented poet, playwright and vocalist Jamila Woods. Advance tickets are $45 and $55 at the door. http://chicago.plusacumen.org/events/dignitychicago/
If delicious sushi, sleek designs and swanky décor is what you seek, it can all be found at Jellyfish. Chef Harold Jurado and sushi chef Andy Galsan have collaborated to create the perfect menus for lunch, dinner and late-night dining. The pan-Asian and sushi offerings include items like kabocha squash skewers, Szechuan king crab, miso-glazed cod, spicy tuna tempura, and of course nigiri and sashimi. The cream-colored leather cushions, off-white specked bar and blue mosaic tiles set the perfect aquatic scene – somewhat reminiscent of a Miami lounge. In warmer weather, the floor-to-ceiling windows overlooking Rush Street open to let in a cool breeze. Sit still long enough, you just might hear the ocean. 1009 N. Rush St.; 312-660-3111
The quick-serve Mediterranean food fixture has expanded from Lincoln Park to the Loop. It’s still the same casual healthy food place that patrons fell in love with. Fresh-baked pita, shawarma, falafel, kabobs and baba ghanoush are staples at Nesh, but it’s the bread that really gets the people going. The oven, imported from Lebanon, is responsible for the traditional pita as well as larger hand-stretched flatbreads for wraps. There’s also a create-your-own salad option and smoothies made from real fruit. 734 West Fullerton Ave.; 773-975-6374
The cozy bakery, formerly known as Phoebe’s Cupcakes, offers a breakfast, lunch and dinner menu in addition to its tasty sweets. Phoebe’s Cupcakes is known for rotating more than 200 signature flavors over the course of the year by featuring 15 flavors a week, and lucky for you, that won’t change. Owner Phoebe Walker’s goal was simply to marry great coffee and espresso with great gourmet pastries and sandwiches. It’s simple comfort food made from high quality ingredients and prepared by culinary school trained chefs. But don’t expect to walk in and be greeted by a maître d’. Phoebe’s still has a mom-and-pop, neighborhood vibe with first come, first serve seating. 3351 N Broadway St.; 773.868.4000
Round up the kiddies and become a part of history at this year’s Great Highwood Pumpkin Festival. HGTV and the Guinness Book of World Records will be on hand to try to break the world record for the most pumpkins being carved simultaneously! $10 gets you one pumpkin, while $20 gets you an all-you-can-carve weekend pass. Pumpkins will later be displayed along through the main drag in Highwood. Attendees can also expect carnival rides and food vendors. Visit the festival’s website for more details.
Rooftop fun shouldn’t be limited to the summer – at least that’s what the folks at theWit believe. The swanky downtown Chicago hotel unveiled the new and improved ROOF on theWit bar that now features a retractable glass roof which means later nights and year-round fun. Despite all the new changes, tasty menu options like roasted artichokes with almonds and tuna crudo will remain the same. Guests can indulge in hibiscus margaritas or mellow out with wine from the Euro-centric wine list; all while sitting 27 stories high in the sky. Evenings can get quite amped, so if you’re not a fan of crowds, an after-work drink might suffice. 201 N. State St.; 312-239-9501
Sip espresso and enjoy city views all while getting your new suit tailored. An unparalleled shopping experience is the focus of the second opening of Suitsupply in the US. Now Chicago fellas can enjoy the Amsterdam-based companies’ tradition of offering the finest Italian fabrics, European styling -- all within an unexpected Gold Coast penthouse with a rooftop -- at an attainable price. From suits and cufflinks, to pocket squares and scarves; there’s no short supply of items that will have you turning heads in the boardroom or a night on the town. 945 N. Rush St.; 312-340-6909
For more places to venture to in Chi Town, head over to Uptown’s Chicago Guides page for listings.