48 hours in Chicago

Where to stay

Housed in a Venetian Gothic building, Chicago Athletic Association is a gathering spot for visitors and locals alike. You can feel its athletic heritage in the gymnasium-inspired accents in each room. Consider the Founders Suite, with original stained-glass windows, fireplaces, and views of downtown. In the evening, head to the Milk Room speakeasy to sip rare spirits and curated whiskeys. 

Alternatively, stay at the Hotel Essex, a modern property on bustling Michigan Avenue that marries retro and contemporary luxury. The classic accommodations offer pops of color and views of Grant Park and Buckingham Fountain. Imbibe at SX Sky Bar, a two-floor space with an open-air area.

Day 1

Kick off your morning at an outpost of Foxtrot Market & Café. Opt for a pour over of locally-roasted Metric Coffee, a nitro cold brew, or a CBD latte. Healthy dishes like crustless quiche with butternut squash and broccolini and blended dragon fruit bowls with chia, berries, and coconut flakes are perfect fuel for the day ahead.

Choose your adventure:

Slide 1 of 2
  • Option 1: Culture

    Chicago is known for its iconic skyline and architecture by notables like Frank Lloyd Wright and Mies van der Rohe. Familiarize yourself by visiting the Chicago Architecture Center. The new location includes the Chicago City Model Experience consisting of more than 4,000 miniature buildings.

  • Option 2: Fitness

    Traverse the town on two wheels. Rent a Divvy at Osterman Beach, the start of the Lakefront Trail. If you’re feeling energetic, tackle all 18.5 miles and end at the South Shore Cultural Center

For lunch, head to , where you can find numerous gluten-free, dairy-free, and vegan options. Try the Boulderado grain bowl with roasted vegetables or the Le Midi kale salad topped with tahini-yogurt dressing. 

Save room for dinner at Café Cancale. Chef Paul Kahan launched the concept in May 2019 following a trip to coastal France. Begin with selections from the raw bar and an order of grilled octopus ratatouille. Smoked eel, incorporated in the yellow chicories salad, is particularly delicious and the trout amandine is a must. Wash it all down with a dry white wine from nearby Michigan.

Day 2

Beatrix in the River North neighborhood is known for its healthy breakfast items like 10-grain oatmeal, quinoa cakes with poached eggs, and Shishito–egg white sandwiches. Order a turmeric chai latte and, if you’re feeling indulgent, an angel food muffin from the pastry case.

Choose your adventure:

Slide 1 of 2
  • Option 1: Culture

    Stroll the elevated 606 Trail, which has 12 access points and was built atop a former elevated rail line in Logan Square. Pop into well-curated shops like Tusk, swing through scenic Humboldt Park, and check out the experiential wndr Museum before heading back downtown.

  • Option 2: Fitness

    Explore the city with a five- to six-mile-long run around Millennium and Grant Parks. Start on edge of Millennium Park (take in Cloud Gate better known as the Bean), then loop around the Art Institute and Grant Park. Continue past the Shedd Aquarium to Northerly Island before heading back.

It’s easy to eat well at Wells Street Market, a new food hall in the Loop. There are 10 restaurants, but make Fare a priority. Start with a bowl of greens or ancient grains, then add toppings like flavorful harissa carrots, sweet-and-sour cucumbers, or miso sweet potatoes. Get your lunch to-go and grab a seat along the Chicago Riverwalk. 

Reserve dinner at . Share vegetable-focused dishes like shaved zucchini with sheep’s milk feta, pine nuts, and mint, or grilled sweet potato salad with sesame yogurt and citrus. End your trip with a nightcap and views of Millennium Park at Cindy’s.

An extra day: Lincoln Common

Visit Lincoln Common, a brand new development in the residential Lincoln Park neighborhood, opening this fall. It’s home to luxury apartments and condos, shops, and restaurants. 

Start the morning at the new Equinox club, perhaps with some laps in the indoor pool. Then stop into Herb + Alchemy, a new sustainably-focused coffee shop serving vegan baked goods and herb-infused coffee. Check out the shops on North Halsted street then visit the Lincoln Park Conservatory, a Victorian-era glass structure that houses exotic plants from around the world. 

Enjoy a Middle Eastern bounty at Galit. Explore the wine list, which specializes in Israeli bottles, then order the Salatim, a selection of salads and spreads with pillowy pitas. Dishes change often, but know that the offerings, especially ones with surprising produce pairings like broccoli and sour cherries, won’t disappoint. Desserts like lemon granita with blueberry compote satisfy a sweet tooth.

48 hours in Milan

There are over 100 miles of cycling paths inside the city.