Whether you’re visiting for the pioneering theater scene, five-star restaurants, world-class cultural institutions, or something else entirely, Chicago truly offers something for every traveler. Inspirato Members stay in an ideal location in the heart of Chicago’s mesmerizing downtown, at the award-winning Peninsula hotel or the stylish and modern Thompson Chicago.

There’s a lot to do in this bustling city. To help narrow down members’ itineraries, we’ve laid out some top recommendations for the best things to do, see, and eat in The Windy City.

Places to See

Downtown Parks

Leave some time for an unhurried stroll through Millennium Park and Grant Park, home to acres of lush gardens, sprawling grounds, Buckingham Fountain, and arguably Chicago’s most famous sculpture — the Bean.

Lake Michigan

Chicago’s iconic skyline is best appreciated from the vantage point of Lake Michigan, so be sure to schedule a harbor cruise or charter your own boat. The sun sets behind the skyscrapers and makes for a gorgeous twilit silhouette. Have your camera ready.

The Art Institute

The Midwest’s most venerable art museum, The Art Institute is home to more than 10,000 pieces of artwork, including pieces by Pablo Picasso, Henri Matisse, Georgia O’Keeffe, and Mary Cassatt. In 2014, The Art Institute was ranked the #1 Museum in the World by TripAdvisor.

Things to Do

Spa Day

The 19th and 20th floors of The Peninsula Chicago are devoted to health and wellness. The spa’s comprehensive menu of services is inspired by Ayurvedic and Asian philosophies. Indulge in a bamboo massage that utilizes the plant to stimulate the flow of energy throughout the body.

Navy Pier

It’s known as the City of Big Shoulders, but this city caters wonderfully to the little ones too. Head to the Chicago Children’s Museum at Navy Pier or let tykes cool off with a splash in the Crown Fountain in Millennium Park.

The Best View

Slip away to The Signature Room, situated 95 floors above Michigan Avenue. The iconic restaurant perched high atop the John Hancock Center offers sparkling views of The Windy City skyline and the lake.

Like a Local

Chicago’s heart might beat downtown but its soul resides in its neighborhoods. Head to Wicker Park for a stroll on the 2.7-mile 606 trail (sometimes referred to as the Bloomingdale Trail), an elevated park built over a former rail line. Exit at Logan Square — one of the city’s trendiest foodie spots — for a bite of fried chicken and a Negroni slushy at Parson’s Chicken & Fish.



Cafe Ba-Ba-Reeba!. This unpretentious (and always bustling) tapas bar in Lincoln Park caters to the whole brood. Parents will be happy with pitchers of sangria, scores of tapas, and larger entrees like seafood paella. Pint-size family members can dig into kid-friendly tapas, like chicken or beef la plancha and vegetable paella.


Mindy’s Hot Chocolate. Savor entrees such as down-home mac and cheese, smoked rabbit, and grilled half chicken. Be sure to leave room for dessert. Chef Mindy Segal — a 2012 James Beard Foundation award winner for “Outstanding Pastry Chef”— crafts a rotating menu of delectable sweets.


Gibson’s Bar & Steakhouse. In a town that’s serious about its steakhouses, Gibson’s Bar & Steakhouse is an institution. It’s the only restaurant group in the country with its own USDA Prime certification. Gibson’s meat hails from sustainable farms in the Upper Midwest and is aged precisely 40 days to perfection by the time it makes it to your plate.

Local Favorite

Frontera Grill. Rick Bayless didn’t make a huge splash on the Chicago dining scene when he debuted his first Mexican restaurant, Frontera Grill, in 1987. But in recent years, his restaurants have exploded in popularity, racking up a slew of awards, including a James Beard Award for “Best Outstanding Restaurant” in 2007.

Things to Know


Hot and humid summer days send locals and tourists alike to the refreshing waters of Lake Michigan; summer nights are balmy, long, and best savored on an outdoor patio. If you can’t stand the humidity, fall is a great time to visit, when the leaves burst into a kaleidoscope of color. Chicago winters can be bone-chilling cold, windy, and snowy.

Getting There

O’Hare International Airport (ORD) is the primary airport servicing Chicago. O’Hare is 17 miles northwest of the Loop, which means you’re a quick cab ride away from downtown, unless it’s rush hour. Then, your best bet is to hop on the CTA’s blue line.

Chicago’s secondary airport is Midway International Airport (MDW). It’s situated just south of the Loop and offers service on five airlines, most notably Delta and Southwest. Again, a quick cab ride will whisk you downtown, or you can hop on the CTA’s orange line if traffic is bad.

Getting Around

One of Chicago’s best qualities is how easy it is to get around without a car. Make use of the CTA, the city’s robust public transit network, which includes several El lines (an elevated subway) and a network of buses. Cabs are plentiful when you need them. Overall, Chicago is wonderfully walkable.


  • Jim says:

    I was the first employee to walk on the property before the grand opening of Great America theme park in Gurnee.
    It was a great difference between this new environment and this Tennessee boy. It was like I was living in a foreign country. Hated the weather. Loved the snow. Didn’t quite fit in with the yankees. Loved the mid west people. Didn’t like the traffic. Loved the “loop”. I could go on and on. Overall, a great experience.

  • Edgar says:

    How could you not mention the Wrigley Field experience?

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