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An aerial view of the downtown Chicago skyline, with a park and beach in the foreground.

3 Days in Chicago: Long Weekend Explorations


Chicago is probably the most interesting and aesthetically pleasing city in the U.S. In fact, Conde Nast Traveller recently named Chicago “Best Big City” in the nation for the fourth year in a row. Between award-winning dining options, epic green spaces, world class museums, and a striking skyline, Residences at 8 East Huron has come up with a three-day itinerary just in time for the Labor Day holiday. So get out, feel like a tourist, take part in urban adventures, and enjoy our fair city.

Day 1 – All About Green Spaces

Fuel up for a fun-filled day at Big Shoulders Coffee, just a short stroll down State Street. From here, catch the Red Line for a 9-minute ride to one of the city’s best outdoor spots: the Chicago Riverwalk. Then, stroll the 1-mile path to Lake Michigan and Lakeview Park, where you’ll find Urban Kayaks. Rent a standup paddleboard or kayak and paddle the calm waters of the bay, or sign-up for a 2-hour guided tour. Either way, you’re sure to enjoy the change in perspective water brings. Afterward, take a break with a picnic lunch in Millenium Park then head back to the Riverwalk for happy hour. Beatnik on the River offers inventive cocktails and small plates with a posh crown and stunning bohemian aesthetic. It’s the ideal spot for low-key celebration of a perfect day.

Day 2 – All About the City’s Energy

Today is about exploring Chicago’s unique energy. Brunch at NoMi Kitchen | Lounge | Garden for thoughtfully sourced ingredients prepared simply and elegantly with a classic French twist. From here, head to The Skydeck at Willis Tower for a touristy moment, enjoy the lofty view of the city in all its glory. Then take time to explore the shopping on streets nearby, before you grab a classic Italian deli lunch at Cafe L’Appetito or walk the short distance to Quartino Ristorante to catch a soccer game and enjoy some afternoon vino. Afterwards, find a seat at ROOF on theWit for a classy, retro experience and a perfect cocktail to keep the party going.

Day 3 – All About Life Outdoors

Even from the heart of the city, there are plenty of opportunities to enjoy the great outdoors. Hop on your bicycle or rent one at Third Coast Cycles for a ride through the classic Chicago streets of Old Town and up to Lincoln Park. Here, you have options. Zip through the stunning paths around Lincoln Park COnservatory or over to the Lakefront for miles of beach and the Chicago skyline. Once you’ve worked up an appetite, land at Theater on the Lake for a Shrimp roll and an ice cold beer on the stunning outdoor patio. Back home at 8 East Huron, rejuvenate from your day with a refreshing dip in our outdoor swimming pool, or if you’ve still got energy to burn, snag a table at Aba in Fulton Market. A short taxi ride west, the chic garden rooftop is the spot to watch the world go by at a pace you set yourself.

The best part about living here is having the option to create your own exploration every day of the week. Have a favorite routine that is uniquely Chicago? Share it with us – we’re always looking for new spots to explore. And stay tuned for more blog posts with food, fun, and lifestyle recommendations.


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