Day One

Morning

Less than a 5-minute walk from the Omni Chicago Hotel, you’ll find one of Chicago’s hottest breakfast spots, Sunny Side Up Brunch & Coffee Shoppe on Wabash and Superior. Guests of all ages will enjoy the indoor and outdoor seating at this charming old house on the corner. The skillets, hash and chilaquiles garner the most praise, but the French toast is another standout. On the other hand, you could enjoy the stunning views of the bustling Chicago streets at 676 Restaurant on the 4th floor of the Omni Chicago Hotel. The banana bread pancakes are a must, as are the waffles, which you can order topped with everything from caramel apple chutney to brown sugar cream.

After breakfast, take your coffee to go and explore the scenic Riverwalk, which allows you to explore the city’s public art as well as enjoy live performances from local musicians, all with the skyline as a backdrop.

If you’re into shopping, you might also stroll the luxury fashion boutiques along Michigan Avenue. This world-famous shopping district, aptly dubbed The Magnificent Mile, features Tiffany & Co., Bulgari, Swarovski, Chanel, Saks, Nordstrom, Alice + Olivia and dozens of other great shopping options.

Afternoon

When the sun comes out in the afternoon, book a 90-minute Architectural River Cruise—a fun, picturesque tour that’s a must on any Chicago bucket list. It’s also regarded as the most popular tour in the city.

If you’d rather continue moving through your afternoon, pop over to Millennium Park, where you can walk, jog, bike or even Segway your way through this 24.5-acre sanctuary. Interestingly, the park sits atop a parking garage and the Millennium Station railway, making it the world's largest rooftop garden. If you do make it to Millennium Park, be sure you take a picture in front of the famous Cloud Gate sculpture, a.k.a The Bean.

For lunch, enjoy Chicago’s famous deep-dish pizza. On the Magnificent Mile, head to Gino’s East off Michigan Avenue and Superior. Just up the street from the River is Lou Malnati’s Pizzeria, and across from Millennium Park you’ll find Giordano’s. Regardless of where you go, you’ll be sure to get a taste of the true Chicago.

Evening

For a night out, head over to the Wicker Park neighborhood. This area is famous for art galleries, chef-driven restaurants and a healthy nightlife. For something fun and different, try eating at Big Star on Damen and Wicker Park. Self-billed as “Tacos, Whiskey & Honky Tonk”, this is raw, street-inspired authentic Mexican food with a splash of whiskey and beer set to the tune of classic rock and country.

If you are up for it, this area has some of the best desserts in the city. Stroll the streets with a coffee or hot chocolate and sample the sweets from Insomnia Cookies, Mindy’s Hot Chocolate, Stan’s Donuts or other local favorites.

Top the night off with artisanal cocktails at The Violet Hour. Be sure to mind the house rules, which bars cell phone use as well as light beer, Jager-bombs and cosmopolitans. Instead, try the signature Hush and Wonder. Or, grab a drink back at your hotel at 676 Bar & Lounge, which offers a whole swath of classic cocktails.

Day Two

Morning

Start your day off right with a hearty breakfast at nearby Grand Lux Café. This stylish yet relaxed restaurant has something for everyone on their brunch menu. Kids will love the “Churro” French Toast with cinnamon-sugar, chocolate and dulce de leche caramel sauce. Try the Crab and Asparagus Omelet for a unique, savory dish. If you’re looking for something other than coffee to start your day, make sure to try the Sparkling Spanish Rose with prosecco, sangria and fresh strawberries. From breakfast beignets to fried chicken & waffles, this spot has plenty of options for the most important meal of the day.
  
After you’re satiated, head to The Field Museum. Perfect for kids, this spot showcases 30 million objects and natural specimens for a scientific museum experience like no other. If the arts is more your scene, you might also get a ticket to the Art Institute of Chicago, one of the oldest and largest museums in the U.S. featuring the work of masters such as Paul Gauguin.

Afternoon

Today has to include a visit to Shedd Aquarium, where you can explore the greatest depths of the ocean—all while in Chicago. Whether you join a tour or go it alone, be sure to allocate a good two to three hours to see all of the amazing marine species on display.

You might also want to check out an iconic part of the city’s skyline: Willis Tower, a 110-story behemoth with expansive views of the city. If you dare, you can even get right on the ledge in a glass encasement for some daredevil sightseeing.

For lunch, try City Winery on the Chicago River, which has the ambiance and scenery you’d expect from its name. The open-air terrace and views will surprise and delight nonetheless. The Gage upscale gastropub is beloved by tourists and locals alike for its inventive menu and cold microbrews. Order anything on the menu with confidence, but be sure to sample and share a Scotch Egg.

Evening

The vibrant West Loop has great dining and entertainment. In this area of former factories, markets and warehouses sits Girl & The Goat. This restaurant was created by West Loop local and executive chef Stephanie Izard, whom you might recognize as the first woman to win Bravo’s “Top Chef”. The wood oven roasted pig face (topped with a fried egg) is one of her most popular, and strange dishes. Then again, the goat liver mousse is not far behind.

Leña Brava is another option by yet another celebrity chef Rick Bayless, who is the host of the PBS show “Mexico: One Plate at a Time”. This restaurant serves steak and seafood with a unique, Southwestern flair that you can’t find anywhere else, like Black Cod “Al Pastor” and Octopus “Carnitas”.

After dinner, the Lone Wolf will welcome you with its house-made libations. Ask for the Beergarita, Frozen Zamboni, Wolfs Blood or go off the menu for the Sgroppino No. 2. Or, head back to your hotel for a dip in the indoor swimming pool or a relaxing session of people watching in the rooftop garden of herbs. You might also grab dessert at 676 Restaurant & Bar—the caramel pot de crème with vanilla Chantilly is a knockout.

If you have more time...

Whether you like baseball or not, in-season or out, visit Wrigley Field, home of the 2016 World Series Champion Chicago Cubs. Catching a game is ideal, going on a tour is memorable, but even visiting the grounds and neighborhood is a noteworthy experience. And if you are a sports fan, try to find time for a cigar and drink at Ditka’s or head over to Harry Caray’s 7th Inning Stretch for a burger and an Old Style.

The Signature Room (95th Floor) and The Signature Lounge (96th Floor) at the 100-story John Hancock Center are ideal for soaking in views of the entire city while you grab a bite or a drink. In fact, on a clear day you can see up to 80 miles across four states (Illinois, Indiana, Wisconsin and Michigan).

Explore the flavors of the Mediterranean at Eataly, a high-quality Italian food market where you can shop, wine and dine. Taste everything from gelato to fresh meat and fish to pizza and pasta.

The Omni Chicago Hotel concierge team contributed to this article.