If you want options, this Uptown brunch institution has you covered with an absolutely exhaustive menu. Choose from pancakes and French toast, eight different Benedicts, breakfast burritos, omelettes and an impressive gluten-free lineup. (We're especially fond of the corn arepas topped with chorizo.) But perhaps the best part about dining at Tweet is checking out owner Michelle Fire's personal art collection on the walls as you slip into a food coma. You'll even find some of the featured artists' go-to dishes on the menu.
Runner-up: Odyssey Cruises Chicago
Music Box Theatre
For movie lovers who don't care for traditional Hollywood blockbusters, there's no better theater than the Music Box, a two-screen cinema that shows the latest art-house films and documentaries. It's gorgeous, and the main theater regularly hosts director Q&A sessions as well as weekly midnight screenings of cult classics. Also, the concession stand here tops its popcorn with real butter.
Runner-up: Davis Theater
Parson's Chicken & Fish
No Chicago summer is complete without a trip to Parson's umbrella-dotted patio for a frozen negroni and a basket of fried chicken. This year, the pristine outdoor area will debut a new bar and kitchen plus more exterior seating (good news for the wait list, we hope). Once you nab a table, choose from frozen tipples, funky beer cocktails, canned beer and classic mixed drinks. Keep the good times rolling with a trip to the Ping-Pong table before you go.
Runner-up: Big Star
Back of the Yards Coffee Co.
This specialty coffee roaster serves an excellent cup of joe and gives back to its namesake community. A portion of all sales goes directly to neighborhood programs that promote peace and education. Beyond that, the shop employs local youth and diverts 95 percent of its waste to compost. On the caffeine front, choose from menu items like Ojo Rojo (coffee with a shot of espresso), cappuccino, horchata cold brew, Toro Loco (cold brew, CO2 bubbles, simple syrup and lime) and drip coffee.
Runner-up: Backlot Coffee Old Irving Park
Located in the basement of the Wrigleyville building that houses Metro, Smart Bar has kept the party going since the early ‘80s (when it on the fourth floor). A vibrant young crowd fills the subterranean club each weekend, dancing to the beat of the venue's world-class Funktion One sound system. Typical bills find cutting-edge DJs from Europe, Detroit and Chicago spinning for the crowd, while the weekly Queen party brings out house music aficionados and drag performers nearly every Sunday night.
Rep Chi keeps its store stocked with plenty of Chicago love. The shop boasts patches, shirts, keychains, hats and more that proudly display the Chicago flag, CTA map and other Chicago-centric designs. Stop here first for gifts for anyone on your list that loves the city or is missing it from afar. The store creates custom designs and crafts gifts made with recycled items.
Runner-up: Savvy Seconds and 1sts
This sunny Rogers Park café has breakfast on lock with hearty scrambles, self-proclaimed "life-changing" breakfast sandwiches, bagels, doughnuts, quiche and more. Whether you're ordering a house-made pastry or a biscuit smothered in gravy, this sweet spot is sure to put a smile on your face before noon.
Runner-up: La Catedral Cafe & Restaurant
Designed by William Le Baron Jenney in the mid-1800s and enhanced several years later by Jens Jensen, Humboldt Park was once the nation’s greatest public park, boasting acres of Prairie-style gardens, grazing animals and a meandering river scene. Though the animals are long gone, the park still offers extensive rose beds as well as tennis courts, an inland beach, baseball fields and bike paths.
Runner-up: Lincoln Park
Bookings at this historic Pilsen concert hall range from Americana to psych rock bands, all presented in a room that retains its character (chipping paint on the walls, original molding around the stage) and sounds excellent. Whether you’re standing on the floor or sitting in the balcony that wraps around the room, you’ll feel like you’re experiencing one of your favorite bands playing in a bygone era of Chicago’s history.
Runner-up: Empty Bottle
If size matters, there's no better bar in Boystown than this well-hung hot spot. Six big rooms—we like the bustling Glass Bar—are all packed with cute, frisky boys distracting themselves with the same three things: the videos on the wall, the drink in their hand and the ass in your jeans.
Runner-up: Big Chicks
Art Institute of Chicago
Guarded by an iconic pair of bronze lions, the Art Institute of Chicago houses a permanent collection of more than 300,000 artworks, displayed in a sprawling complex of galleries and halls. You’ll find everything from Japanese prints to ancient Greek sculptures among the pieces housed in the museum’s central galleries, where classic paintings such as Edward Hopper's Nighthawks and Grant Wood's American Gothic are also housed. For something a bit more contemporary, head for the Modern Wing—a Renzo Piano-designed addition that displays the museum’s architecture and design collection as well as 20th- and 21st-century art.
Runner-up: Museum of Contemporary Art
This 24.5-acre park is one of the most popular gathering spots in the city, known for its free concerts, famous public art installations and its proximity to the Loop. The centerpiece of Millennium Park is the Jay Pritzker Pavilion, a flowing Frank Gehry-designed structure that hosts of the city’s biggest outdoor festivals and concerts. You’ll also find the serene Lurie Garden, al fresco dining destination the Park Grill and pedestrian bridges that lead to the Art Institute and Maggie Daley Park. Welcome to the hub of Chicago’s front yard.
Runner-up: Buckingham Fountain