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Destination Guide: Chicago

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Why do we love Chicago? It’s not just the pizza (although we do like diving into a deep dish). It’s because Chicago’s a great destination for any travel budget. If you want to splurge, shop the Magnificent Mile and order a $250 Tajima Kobe beef filet at Benny’s Chop House. If you prefer simpler pleasures, treat yourself to a Chicago dog and a bleacher seat at Wrigley Field. Or, just find a spot on the beach and admire the skyline.

We’ll help you plan your getaway with this quick guide to the best Chicago activities, hotels and restaurants.

5 Fun Things to do in Chicago

  1. Visit The Bean. Chicago’s iconic sculpture, the gleaming “Cloud Gate” (aka The Bean) is a must-see spot for visitors. After the obligatory selfie, explore Millennium Park, where (depending on the season) you might find a concert, a food festival, or ice skating.
  2. Take an architecture boat tour. It may sound dry, but a boat tour offered by the Chicago Architecture Foundation is one of the most fun things you can do in Chicago. See the city from a different angle as engaging guides explain why Chicago is so clean (the secret? Its alleyways) and how engineers reversed the flow of the Chicago River in 1900.
  3. Hit the beach. On a glorious summer day, you can sit on the shore of shimmering Lake Michigan and feel like you’ve been transported to the Caribbean. Chicago has some great beach bars, too. We love Caffè Oliva, a relaxed spot on Ohio Street Beach with excellent mojitos.
  4. Tour Wrigley Field. If you’re in town for a Cubs game, get tickets and soak in the ambiance of this beloved ballfield. Even out of season, a Wrigley Field tour is an experience you won’t forget. You’ll see the ivy-covered outfield wall, the press box, the Cubs’ dugout and other features (depending on the day).
  5. Stroll the Magnificent Mile. Do designer boutiques make your heart sing? Then you’ll want to dedicate a morning to walking North Michigan Avenue, home to Armani, Tiffany, Prada, and Chanel, among other brands. If your style leans more boho than Burberry, shop the artsy shops and galleries in Wicker Park.

4 Fantastic Boutique Hotels in Chicago

For traditional tastes, we have a couple of Chicago boutique hotels to suggest. Built in 1919, The Drake is the epitome of Gilded Age glamour, the spot where celebrities and gangsters once mingled. Marilyn Monroe and Joe DiMaggio, newly married, even carved their initials into the Drake’s wooden bar. Don’t miss afternoon tea in the Palm Court.  

There’s also the Hotel Lincoln near Wrigley Field, a fun and pet-friendly hotel that’s known for excellent food and original art. The hotel, built in the 1920s, once had a speakeasy frequented by Al Capone.1

And if you like modern style more than vintage digs? You can’t miss The Godfrey Hotel’s dramatic Cubist façade in the River North neighborhood, close to the Magnificent Mile. Perks include crisp rooms, a well-equipped gym, and a rooftop lounge. The Guesthouse Hotel offers well-appointed suites with kitchens and private balconies. Guests praise the super-cushy furnishings and helpful staff.

3 Great Places to Eat in Chicago

Allianz - Chicago Pizza

There are three things you have to eat on your trip to Chicago. Number one, of course, is deep-dish pizza. Head to Gino’s East, which bakes its cornmeal-crust pies in cast-iron pans. Write your name on the wall, if you’d like, and order the Chicago Fire with sausage, fire-roasted red peppers, and red onions.

The second is a Chicago-style hot dog. This is a delicious mess, usually defined as an all-beef dog on a poppyseed bun, piled with relish, onion, tomato, peppers and a pickle spear, plus mustard and celery salt.2 Don’t even think about adding ketchup. Experts disagree on where to find the best Chicago hot dog, but we’ll suggest the Superdawg Drive-In. It’s classic spot with two hot dog sculptures on the roof named Flaurie and Maurie, after the founders.

The third dish might surprise you: It’s a jibarito, a sandwich invented in Chicago by Puerto Rican restaurateur Juan "Peter" Figueroa.3 Instead of bread, the jibarito is made with flattened, fried plantains; in the middle you’ll find garlic mayonnaise, lettuce and tomato, steak (or chicken) and cheese. Serious Eats names La Bomba as the best place to find a classic jibarito.4

Ready to jet off to the Windy City? Don’t forget travel insurance. Trip insurance is invaluable even for short domestic trips, protecting you in case of flight delays, lost luggage and covered trip cancellations. Find the plan that's right for you!

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