Located in the heart of the Midwest, a visit to Chicago gives way to a welcoming, navigable city packed with entertainment, dining and cultural options that make it truly world-class. Home to the first skyscraper, an incubator of improv, die-hard sports fans, and cutting edge cuisine, the Windy City is a great weekend escape or longer excursion.
10AM GREEN CITY MARKET
Start your day at Lincoln Park’s Green City Market, a farmer’s market like no other. The variety here is mesmerizing (purple asparagus, elk meat, cheese curds, farm made pasta), and comes from farms near and far, bearing fruits, vegetables, dairy, protein, flowers, herbs and more.
12PM PORTILLO'S HOT DOGS
100 W. ONTARIO ST. CHICAGO, IL 60654
If you want a true Italian Beef or Chicago Dog beyond the street cart, your only option is Portillo's. A cult classic in the Midwest, from their killer cheese fries to the immense chocolate cake, it's no wonder that all 45 locations always have lines out the door.
2PM WRIGLEY FIELD
Whether you're a Cubs fan, Sox fan, or not a sports fan at all, Wrigley Field is one of the most iconic baseball stadiums in the country, and worth paying homage to. Whether you're visiting in summer and able to catch a game amid the ivy outfield, or just snapping a photo in front of that infamous red sign, it's 100+ years of history in the making. Wrigleyville, the surrounding area has a bunch of fun, young bars to check out that are easily accessible via the Red Line on the El.
4PM CHICAGO TOUR
See Chicago from above! With this do-it-all tour through Viator, you and your family will get early access into the Skydeck at Willis Tower, enjoy a 75 minute cruise around the city and take a trolley tour to some of the cities best museums.
6PM GIRL AND THE GOAT
The first female winner of Top Chef, Stephanie Izard's Girl and the Goat was opened to endless acclaim that lived up to the hype, including being dubbed “America’s Best New Restaurant” by Saveur magazine. It was nominated for the 2011 James Beard Best New Restaurant Award right around the time Stephanie was named one of Food & Wine magazine’s Best New Chefs. Always packed, if you can't get a reservation (and yes, you need one), the Little Goat diner right across the street is equally delicious and even more affordable.
9PM VIOLET HOUR
1520 N. DAMEN AVE. CHICAGO, IL 60622
With bartenders that actually know how to make a drink, when you’re ready for a nightcap, there's no better place for libations than the Violet Hour in Wicker Park, an upscale, semi-secret speakeasy with rules that include, “No O-Bombs. No Jager-Bombs. No bombs of any kind.” Opt instead for a reliably strong classic drink like a Manhattan or one of their speciality artisanal cocktails.
9AM THE BONGO ROOM
With a few locations sprinkled throughout the city (South Loop, Wicker Park & Andersonville), the Bongo Room is known for their decadent brunches from white chocolate carmel pretzel pancakes (yes, you read that right) to a chocolate french toast tower piled so high you'll need an army to even make a dent. Pro tip: their benedicts are equally as good so if you're craving a savory breakfast, an off-the-menu option is to get just one of their fancy pancakes on the side. Who said you can't have dessert before noon?
10AM MILLENNIUM PARK
Then take a walk around Millennium Park, the pride and joy of Chicago. Surrounded by the serenity of Lake Michigan and the buzz of downtown, the 24.5-acre park is home to more than 500 free events of the year, from concerts to festivals, dance and theater. Performances take place at the Jay Pritzker Pavilion, a sculpture, in and of itself, designed by Frank Gehry, which is as accessible to the audience in seats as it is to those sharing picnics in the lawn. Other highlights include Cloud Gate, aka “The Bean,” a reflective sculpture designed by Anish Kapoor, that mirrors the sky and skyline, the five-acre Lurie Garden and Crown Fountain.
12PM PIZZERIA UNO
There's a longstanding debate about where in Chicago has the best deep dish and ask any three Chicagoans and you'll get three different answers (probably Lou Malnati's, Edwardo's and Due being included). However, if you want to go straight to the source, Pizzeria Uno's is the original deep dish purveyor, slinging cheesy, tomato-ey goodness since 1943. Just bring your appetite.
1PM ARCHITECTURE RIVER CRUISE
In the afternoon, learn about the past, present and future of Chicago while floating down the Chicago river, gazing at the surrounding skyscrapers. The Chicago Architecture Foundation’s Architecture River Cruise is a must for every Chicago visitor, whether you know who Mies van der Rohe is or not (you will by the end of this trip).
3PM BIKE THE LAKEFRONT / NAVY PIER
Spend the afternoon sightseeing on a beautiful bike ride down the lakefront. Boasting 18 miles of car-free paths, enjoy sandy beaches, scenic parks, stunning architecture and spectacular views of the city. Bikes can be rented from various kiosks around the city via Divvy or Bike and Roll. If you have kids in tow, you may want to plan a stop at Navy Pier to enjoy the 15-story ferris wheel or other attractions.
401 N. WABASH AVE. CHICAGO, IL 60611
If you want to splurge for your last meal, steal away to the Michelin-starred Sixteen (on the 16th floor of the Trump Hotel Chicago) which, at 92 stories, is the second tallest building in Chicago, just behind the Willis (formerly Sears) tower. Perfect for a fancy evening affair or just a nightcap, gaze at iconic buildings such as Tribune Tower and the Wrigley Building as you sip your bubbly, far, far above the city. If you time it right, you just may catch the sunset.
9PM SECOND CITY
Famously inspiring guffaws since 1959, Second City is one of the country's premier sketch comedy and improv theaters. With a rotating calendar of shows, there's always somewhere to get your laugh on. Notable alumni include comedic greats like Andy Dick, Mike Meyers, Chris Farley, Amy Poehler, and countless others.
WHERE TO STAY: THE TRUMP HOTEL
401 N. WABASH AVE. CHICAGO, IL 60611
The Trump Hotel Chicago is pretty spectacular and located right downtown, so it is a great base from which to explore the city. One of the most upscale hotels in the city, it's A+ customer service.