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Heading to Chicago? If you’re heading out for the first time to the Windy City, it can be overwhelming. The city of over 2.5 million residents is sprawling and features incredible dining, world-class museums, towering skyscrapers and more. For your first time, there are some things you can’t leave Chicago without experiencing. Check out our guide to Chicago for first-time travelers.

Title Chicago for First Time Travelers By Semmick Photo-Shutterstock.jpg
By Semmick Photo-Shutterstock


There is so much to do and see in Chicago that we couldn’t possibly name it all, but for your first time in town, here are the classic sights you can’t miss.

Millennium Park

Millennium Park By Lucky-photographer-Shutterstock.jpg
By Lucky-photographer-Shutterstock

You have to stop by this classic tourist park during your stay in the city. Millenium Park is home to Crown Fountain, where you can cool down on a hot summer day. Wander down the unique, spiraling BP Bridge that gets you across the major roads to Maggie Daley Park (also a part of Millennium Park) or find a concert or event at Jay Pritzker Pavilion. In the summer, the pavilion hosts the Grant Park Music Festival, a summer-long event of free nighttime concerts and family-friendly fun. And of course, no trip to Millenium Park, or Chicago for that matter, is complete without a visit to Cloud Gate, AKA the Bean. Cloud Gate was constructed in 2006 by British artist Sir Anish Kapoor and was designed as a way to reflect the towering skyline of the city while also acting as a gate, letting people walk through the Bean to the rest of the park.

Shedd Aquarium

Traveling with kids? Head to the Shedd Aquarium. Located in Grant Park just below Millennium Park, the aquarium opened in 1930 and is one of the biggest indoor aquariums in the United States. Shedd Aquarium features over 30,000 different species of sea life, as well as reefs and educational tours to learn more about the animals and their habitats. The aquarium has five main areas: Waters of the World, Caribbean Reef, Amazon Rising, Wild Reef, Abbott Oceanarium, and Polar Play Zone, each one focusing on a different aspect of marine life and habitats.

Wrigley Field

Wrigley Field By Heather Maguire-Unsplash.jpg
By Heather Maguire-Unsplash

Take us out to the ballgame at Wrigley Field. One of the country’s oldest stadiums of the country’s oldest sport is right here in Chicago. Wrigley Field opened in 1914, making it the second oldest in the United States. Today, the stadium is the home to the Chicago Cubs, the winners of the 2016 World Series. Head out to one of the games and cheer amongst the passionate Chicago fans, or head to the stadium during the day for a tour and history lesson. The field is as classic American as, well, baseball and apple pie.

Willis Tower Skydeck

By Tim Trad

Looking to see all of Chicago at once? Head over to Willis Tower. The building, over 1,000 feet high, features a glass floor Skydeck for you to watch the city below your feet. The box juts out of the building, adding an element of thrill to it, if you dare. For the best views, and the smallest crowds, it’s best to head over at night. In the fall and winter, Willis Tower Skydeck is open until 8 pm, and in the spring and summer, the spot stays open until 10 pm.

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While in town, you have to try some classic Chicago dishes. The city is known for certain foods and treats, and while you can find them in other parts of the US, it’s honestly just not the same as enjoying it in its home city while staring up at the Sears Tower above.

Deep Dish Pizza

Deep Dish Pizza By TMON-Shutterstock.jpg
By TMON-Shutterstock

You’ve heard of it, maybe you’ve even tried it before, but that doesn’t mean you shouldn’t experience the original recipes and flavors of a Chicago deep dish pizza in its hometown. Deep dish pizza has a thick crust, making it more like a flatbread. The pizza is baked in a deep, round pan, similar to a cake, giving it its signature crust. In some variations, the crust is stuffed with cheese or meats, giving the pizza multiple layers. While in town, the best deep dish pizza can be found at Pequod’s Pizza at Lincoln Park.

Chicago Style Hot Dogs

Chicago Style Hot Dogs By Brent Hofacker-Shutterstock.jpg
By Brent Hofacker-Shutterstock

You might be thinking “what’s so special about a hot dog?” but before you cross it off your list, be sure to try a classic Chicago dog. The city’s famous hot dog variation is a Vienna beef hot dog on a poppy seed bun topped with standard yellow mustard, white onions, sliced or wedged tomatoes, sport peppers, sweet relish, speared kosher pickles, celery salt, and absolutely no ketchup. The exact date of creation remains unknown, but the Chicago dog is one of the most classic Chi-Town dishes you could try during your stay.

Italian Beef

Another Chicago classic, this is a sandwich you have to try during your visit. The Italian Beef is a sandwich of thinly sliced roast beef on an Italian roll. Acceptable variations on the classic sandwich feature sandwiches dipped in the meat juices. This can vary from just damp to dripping to absolutely soaked. Other variations include an additional grilled sausage, sweet peppers, giardiniera, provolone or mozzarella cheese, and pre-cooked bread. For the best sandwich, head to Al’s Italian Beef, right in the heart of the city.

Where to Stay

South Loop

South Loop By Atosan-Shutterstock.jpg
By Atosan-Shutterstock

If you want to be close to all the best of Chicago, including Grant Park, Shedd Aquarium, and the Field Museum, definitely head to the South Loop. This neighborhood sits along Lake Michigan with easy access to tons of Chicago history, like Millionaire’s Row and Motor Row District. South Loop is home to many old factories and warehouses that have been converted in recent years to become new office spaces or homes. Check out the charming or modern apartments where you can find Airbnbs to let you live like a local in Chicago’s South Loop.

Chicago Riverwalk

Chicago Riverwalk By Thomas Barrat.jpg
By Thomas Barrat

Charming, upscale, and perfect for your stay — Chicago Riverwalk. The area around the center of the city spans from Lake Shore Drive to Lake Street along the Chicago River. The area is home to McCormick Bridgehouse & Chicago River Museum, Michigan Avenue Bridge, kayak adventures on the Chicago River, boat tours of the city, and tons of waterfront dining, music, shopping, and more. The area is also home to tons of hotels for you to stay right in the center of all the action. If you’re traveling with your furry best friend, don’t fret! Even Chicago’s high-class riverwalk has dozens of pet-friendly hotels.

Magnificent Mile

Another top neighborhood centrally located in the city is Magnificent Mile. The area runs down Michigan Ave and features some of the most high-class shopping, dining, and hotels in the city. Check out classic landmarks like Fort Dearborn, Tribune Tower, Old Chicago Water Tower District, John Hancock Center, One Magnificent Mile, Chicago Place, Water Tower Place, and more. The area is home to hotels like the Four Seasons Chicago and the Ritz Carlton Chicago, perfect for a luxury stay in the Windy City.


Transportation By R Scapinello-Shutterstock.jpg
By R Scapinello-Shutterstock

If you’re only in town for a short time and have a short budget, take the train! Chicago’s metro system, or El, gets you anywhere and everywhere you need to be in the city and is close to all the major tourist attractions. The CTA offers visitors a three-day pass or a seven-day pass at lower costs than buying each ticket individually.

If you’re in the city by car, the city is a grid, making it easier to navigate your way around the streets and neighborhoods. Chicago has some free apps for smartphones, like ParkChicago, to always find easily accessible parking spots and other information. Be sure to have GPS on you, as well.

If you’re looking for other modes of transportation, Chicago was listed as one of the top pedestrian and bike-friendly travel destinations. Rent a bike through Divvy, the city’s public bike share program, or just be sure to pack a good, sturdy pair of walking shoes and head out!

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