5 can’t miss experiences in Chicago

Chicago is sometimes overlooked by visitors, who have heard more about NYC, Miami and San Francisco, but it’s a delightful discovery that many miss out on. As a New Yorker, I loved strolling along the riverfront, with its aquamarine water (a beautiful color, thanks to water from Lake Michigan), the clean air, lack of crowds, friendly vibe, and, similar to NYC, great food.

1. Sail on an evening boat cruise to watch the fireworks

Whether you’re on a couple’s getaway or family vacation, an evening boat cruise on the river and Lake Michigan is a great way to enjoy the illuminated city skyline, culminating in the perfect vantage point to take in the fireworks. During the summer, fireworks are at 9:30pm on Wednesdays and Saturdays. If you’re visiting as an extended family, or for an extra special romantic touch, consider a private yacht charter.

Chicago Fireworks-460-385

2. Savor delicious dining for foodies

Chicago offers amazing dining for foodies — everything from 3 Michelin Star Alinea by Chef Grant Achatz to gracious French cuisine at Les Nomades to innovative farm-to-table modern American at Allium to bustling no-reservations wine bar Avec to a plethora of ethnic food, from Indian to Greek to Thai.

Allium Restaurant Chicago-460-385

3. Delight in lake views from Four Seasons Chicago

The Four Seasons Chicago, unlike many city hotels that also include private residences and condos in the same building, occupies the top floors (30th to 46th) of its tower in Chicago’s Gold Coast neighborhood, steps from the shops of the Magnificent Mile. This means that it offers the highest hotel rooms in the city, and lake-view rooms and suites offer spectacular views of Lake Michigan. There’s also an indoor swimming pool and Jacuzzi, and of course superb Four Seasons service. I’ve never had a more personalized welcome amenity (my favorite brand and flavor of yogurt was waiting for me on arrival)—the staff here really does go the extra mile.

Chicago-Four Seasons Chicago Lake View

4. View Impressionist masterpieces and more at the Art Institute of Chicago

The Art Institute of Chicago is one of the great art museums of the world, and should not be missed, whether you want to take in Impressionist masterpieces by Monet, Degas and Renoir, Post-Impressionist works by Seurat, Gauguin and Van Gogh, or investigate the museum’s collections of ancient and Byzantine art, Asian art, American Indian art, photography, modern art, and more. If you have kids, don’t rule out a visit—they may well be fascinated by the stained glass and armor in the Medieval section, the Egyptian mummy, or the depictions of Greek and Roman gods and goddesses.

5. Explore Chicago by foot with Inside Chicago walking tours

One of my favorite things to do when visiting a city is to take a walking tour led by a local guide, and Inside Chicago Walking Tours, led by Hillary Marzec, was a highlight of my recent stay. I took the “At the Heart of the City” tour of the Riverfront and Magnificent Mile, and Hillary brought the city’s history to life through its architecture, sharing with us both tragic and humorous anecdotes, while also sharing tips on where to take the best photographs.

Inside Chicago Walking Tour-460-385

If you’ve been to Chicago, what were your favorite experiences?

Hilary Stockton is the CEO at TravelSort.

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Comments (4)

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  1. Bob Merrick says:

    I have always considered New York a great city to visit. I have been there many times, but never to Chicago. I have friends who have been to Chicago and they tell me that Chicago is even better than New York. I have decided to put this on my bucket list. Your blog has convinced me to go there. I find all four things that you mentioned worth trying. I am convinced to stay at Four Seasons while visiting there. A walking tour would be great as well as the experience of the fireworks. As a foodie, I always enjoy good cuisine and I heard that Chicago has some of the best. Thanks for such a great article.

  2. Roberto says:

    It was great to read about these options to see and do in Chicago. I am planning to go there and will take them into account.

    Greetings from Argentina!

  3. Anne says:

    Other ideas for Chicago: try the Palmer House for a step back in time in a grand old hotel with a terrific bar; the architecture cruise down the Chicago river on a hot summer’s day; and don’t forget Daley Plaza for Picasso and the Blues Brothers, too.

  4. Sarah says:

    I was there a decade ago and experienced the ‘Prohibition Tour’ which was astonishingly good fun. Our trip also coincided with the food festival around July 4th in Grant Park and I’m yet to find one just as delectable. Chicago is one of my favourite global cities in the world.

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