From Sunup to Sundown and Beyond: How to do Chicago in a Day

1. Watch the Sun Rise

Start your morning at the Adler Planetarium Skyline Walk watching the sun come up over Lake Michigan. Bring your tripod and catch pictures of the city lights across the water from the northwest part of the semi-circular walk. Sunrise colors reflect pink, lavender and orange in the glass buildings. Follow the sidewalk around to the east side of the planetarium for an unobstructed view. Feeling romantic? The sidewalk runs along the 12th St. Beach where you can wiggle your toes in the sand and stroll hand-in-hand with your significant other. Afterwards, take a leisurely stroll through the surrounding Grant Park and nosh on challah French toast at Yolk.

2. Walk the Walk

After breakfast, connect with the Chicago Riverwalk. Get your camera ready—you’ll spot 18 movable bridges within 2 miles. Watch giant gears in action on the first level of the McCormick Bridgehouse & Chicago River Museum. Afterwards, meander through the museum’s tower. Five floors of exhibits culminate in a panoramic view from the top. If you’ve been thinking of redecorating your home, you won’t want to miss Merchandise Mart. The Mart is the world’s largest commercial building, standing 25 stories high and taking up two full city blocks. Don’t worry about trying to see everything in the building—design shops open to the public cover a mere six floors.

3. Stroll Through the Park

Head over to Millennium Park for your midday meal. You’re sure to spot one of Chicago’s many ethnically diverse food trucks on the streets flanking the park. If you prefer to plan ahead, stop by Al’s Italian Beef to try one of the city’s signature thin-sliced beef sandwiches smothered in sweet and spicy peppers. You’ll also find the famous natural casing Chicago dogs here. After lunch, check your teeth and take “selfies” in the reflective stainless steel surface of the Cloud Gate sculpture. Watch water spurt from the mouths of 50-foot-high faces projected on the towers of the Crown Fountain, and don’t forget to stop and smell the flowers at Lurie Garden.

4. Sip Cocktails in a Speakeasy

Although the Green Door Tavern opened in 1921, its history goes back much further. It’s one of the first buildings built after the Great Chicago Fire of 1871 and one of the few remaining wooden structures in the Central Business District. If the building looks a little “tipsy,” don’t worry. The leaning building is structurally sound. Stick around after 5 p.m. and head downstairs to The Drifter, a historic speakeasy. Let the bartender whip you up a speakeasy-era French 75, made with gin, champagne and sour mix topped with a lime and cherry. While you sip your drink, you might even get treated to entertainment ranging from belly dancers to piano players.

5. Call It a Day

Watch the sunset over the city from the 103rd floor of the Willis Tower on the Skydeck. The deck stays open until well after dark every day of the year. You’ll get panoramic views in every direction—the tower is the tallest in the Western Hemisphere. Step out on The Ledge if you dare. The glass-floored viewing platform gives a true bird’s-eye view from 1,353 feet up in the air. Leave your tripod behind, as you can only bring monopods to the Skydeck. After the sunlight fades and the city lights are at full twinkle, head across the street to Giordano’s to taste a traditional stuffed deep dish pizza. Try the Chicago Classic, brimming with pepperoni, mushrooms, onions and green peppers.

6. Be Very Entertained

In addition to checking out the city’s famous attractions, you can enjoy an evening entertainment that is uniquely Chicago. Call a cab or rideshare service and head off to the races on Friday nights at Big Joe’s 2 & 6 Pub. Turtle races, that is! Get there early to earn tickets for your chance to be a contender. You’ll win a free t-shirt if your turtle wins, or a consolation beer if yours is dead last. Next, trek three miles away to one of the city’s most culturally diverse bars, Berlin, whose customers run the spectrum when it comes to ethnicity and lifestyle. Shows vary from Goth to drag and everything in between, all set to a backdrop of grinding rhythms and uninhibited dancing.

7. Close Down a Late-night Bar

Don’t waste the rest of your single day in Chicago waiting in the airport. Old Town Ale House stays open until at least 4 a.m., and will have you feeling like a local in no time. Portraits of the bar’s regulars through the years share wall space with racy renditions of politicians, all painted by owner-artist Bruce Elliot. The jukebox plays blues and jazz, an ode to musicians that once frequented the joint. Old Town Ale House serves beer, chips, and the occasional dog biscuit for canine patrons.

Ready to travel? Find hotels in Chicago.