Checking Into: Chicago

Advisor - Payton Brown
Curated By

Payton Brown

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  • Chicago

  • Arts & Culture

  • City Travel

  • History

  • Architecture

  • Foodie

Body of water and city
Curator’s statement

Chicago is a large metropolis located in the Mid-West of the United States that hosts a vast opportunity to learn about history or immerse yourself with art. Chicago developed into the expansive city that we know today and is popular for its walkability and convenient transit options to tour is town. You can spend time on the river walks surrounded by aesthetically designed skyscrapers, tour the streets and view wonderfully crafted artistry, or connect with locals over delicious deep-dish pizza.

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Insider knowledge

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Where to stay in Chicago

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Hotel Saint Clair - Magnificent Mile

A luxurious and stylish haven nestled in the heart of Chicago's iconic Magnificent Mile, offering exceptional comfort, impeccable service, and breathtaking views.

Thompson Chicago, by Hyatt

Experience contemporary elegance and world-class hospitality at Thompson Chicago, a Hyatt-affiliated hotel blending sophistication, modern design, and exceptional amenities in the heart of the city.

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  • Hotel / resort credit.

  • Welcome amenity.

  • Breakfast daily.

  • Upgrade & extended check-in/out, whenever possible.

Hyatt Centric Chicago Magnificent Mile

Discover the perfect blend of modern comfort and urban excitement at Hyatt Centric Chicago Magnificent Mile, where stylish accommodations, personalized service, and prime location meet to create an unforgettable city getaway.

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Advisor - Payton Brown

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Things to do in Chicago

Navy Pier is a 3,300-foot-long pier on the shoreline of Lake Michigan.

River Boat Tour - Enjoy a boat ride down the Chicago River and learn about the city's architecture and history. Highly recommend for first time visitors. Suggestion: bring a jacket during the colder or cooler months - it is cold on the water.

Chicago Bean - Visit the Bean or "The Cloud Gate" sculpture at Millennium Park.

Willis Tower - Formerly known as the Sears Tower, you can visit the observation deck of this 108-story skyscraper and view the city.

Navy Pier extends over into the Chicago River and offers many outdoor attractions, shopping, restaurants, and family friendly excursions.

Catch a Game - During MLB season, catch a Cubs game at Wrigley Field or if you would just like to visit, there are tour options as well.

Chicago Craft Brewery Barrel Bus - If you like craft beer, enjoy a uniquely guided bus ride around the city and visit 3 breweries. Sample of beer included.

Hop On Hop Off Big Bus Tour - If you want to tour the city at your own pace, you can purchase a 1-2 day unlimited bus ticket and visit attractions around the city. This is a great option if you do not have a vehicle on your trip.

Howl at the Moon - Packed with fun and great for a night out on the town. Known for the best live music in the city, this place is great for private event or parties. Open 7 nights a week, make plans to enjoy a show. Make sure you eat first (no food served).

Places to eat & drink in Chicago

Chic Italian eatery with a riverfront terrace offering craft pizza & pasta, grilled seafood & wines.

For a twist on both Middle Eastern and Mid-Western flavors, Beatnik on the River is a chic and fun cocktail bar and restaurant that will give you a glimpse of food from around the globe. Reservations suggested. Recommendation: Shakshuka for Brunch and a Jungle Bird cocktail

The Hampton Social is a coastal cuisine, American restaurant that has a light, bright and airy ambience. Popular for its brunch, you can't go wrong with the Gatsby Breakfast or experience the Ocean Eyes cocktail.

If you like dinner and a view, Offshore Rooftop is the best in the city. Located at Navy Pier, enjoy some shareables, minis, or mains while taking in Chicago's skyline. Reservations suggested. Fan favorite: Faroe Island Salmon and a Bad & Boujee cocktail

A cute and trendy Italian restaurant named The Albert is a great place to sit down for a nice, elegant dinner. Many choices for pasta are available, but my favorite is the truffle flavored Ravioli paired with glass of wine. Not wanting carbs? They have anti pasta options, too!

Visiting restaurant row? Girl & the Goat was established as one of the first spots to open on the West Loop. This restaurant is a cute and quaint place to enjoy a meal on the patio and soak in some sun. Recommendation: Goat Empanadas and Off Color Brewing's Beer for Tacos

Riverfront facing, Pizzeria Portofino is the perfect place to enjoy specialty pizzas right on the river. In addition to pizza, they have seafood and pasta options to choose from. What is special about this place is if you are enjoying your day on the river by boat, they do have an accessible boat dock for customers.

Another staple to Chicago is Giordano's where you can indulge in their famous deep-dish pizza. This is a great option to feed a group or family for a reasonable price and also get to experience Chicago's finest. Fun fact, you can also ship a frozen pizza to your house if you want to bring a little bit of Chicago back or share with someone special.

With its original location built at Wasbash Avenue and Ohio Street in 1943, Pizzeria Uno is another famous pizza joint. If you are looking for casual dining or comfort food, step into Pizzeria Uno to enjoy authentic choices of freshly made pizzas or entrees. You can take it a step further and book a cooking class, too!

Downtown Night Life Spots

Need to Know

For more travel tips, check out Fora Advisor Abby Kulwicki’s guide, Chicago Must-Sees.

Advisor - Payton Brown

Travel Advisor

Payton Brown

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This guide is part of our ongoing series on travel to Chicago.