Great weekend in The Windy City

It’s not easy to capture Chicago in a weekend, but if you’ve made it a point to see the best of what the third largest city in the U.S.A. has to offer then we can help. The winter might leave you wanting for more, but visit Chicago in the Summer and you’d be hard pressed to find better weather in the country. There are clear time constraints on enjoying the outdoors in Chi-Town, and the locals know it.

Rooftop terraces cover most apartments, from low-lying brownstones to towering skyscrapers, parks are busy and well cared for, and the restaurant and bar scene immediately spills out onto the surrounding streets when the climate gets just barely warm enough. Follow the locals lead and use your time wisely, soaking up as much of that perfect sunshine and warm lake breeze as possible during your weekend escape.

Friday Night

After you are well settled into your hotel, head out for your first slice of deep dish pizza. Yes, there is an endless amount of good food in this city, but there is something so alluring about participating in the ongoing pizza debate. New York or Chicago? It doesn’t matter, really, all that matters here is that the pizza is delicious. Pequods Pizza is one of the more famous places to get it, boasting awards like “Top 5 Pizza in the Country” and “Best pizza in Illinois.”

Afterward, if you haven’t fully submitted to the exhaustion of eating through multiple slices of 2-inch thick pizza crust, stop off at one of the cities fun rooftop bars. Check out Cindy’s for great views of the lake and the bean in Millenial Park while you sip.

Saturday Day

Spring out of bed and hustle out the door to the best breakfast you’ll have all year. The Publican, which is also open for lunch and dinner, has made quite a name for itself in recent years. The brunch features highlights like Porchetta and homemade Weisswurst. It’s busy, so make this reservation well in advance.

Once you’ve had your fill, ride the elevated subway line out to Wrigley Field and take in a Cubs game at one of the oldest baseball stadiums in the country. If the Cubs aren’t in town, try out a kayaking trip on Lake Michigan to get a view of the city that most visitors and locals never see.

Saturday Night

Dinner will depend on how your day went. If you’ve been drinking Coors Lights at the Cubs game, you might be more interested in a burger from Au Cheval. If you paddled away the daylight hours, clean up and step into Chicago’s world-renowned fine-dining scene. Alinea is one of the cities most famous, making regular appearances on the list of top 50 restaurants in the world and carrying the prestigious recognition of 3 Michelin stars.

Sunday Morning

Start your last day in Chicago off with a run, walk, or bike ride along the Chicago lakefront trail. Extending for miles in both directions, the sparkling waterfront views make it easy to slip into a trance and forget you are in a massive city. Either en route or once you’re finished, make time to stroll through Chicago’s well-loved Millenial Park, home to the famous “Chicago Bean” statue.

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