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How To Spend 5 Days In Chicago

How To Spend 5 Days In Chicago

Picture of Elizabeth Newhart
Updated: 2 September 2016
Whether you’re visiting from across the pond, out of state or just outside city limits, Chicago is the perfect city escape.

What to Do

Visit Millennium Park

Chicago’s 24-acre green community space dominates the Loop’s east side. Take a picture at the popular Cloud Gate bean, designed by famous Indian sculptor Anish Kapoor, go for a stroll through the gardens or enjoy a free movie or live music show at the Jay Pritzker Pavilion.

Explore the Lakefront Path

Whether you do it on foot or by bikes, blades or boards, nothing beats the sights and scenes of Lake Shore Drive. With Lake Michigan on one side and towering skyscrapers on the other, there’s no better place to spend a sunny Chicago day.

Attend a Cubs Game

As the second-oldest ballpark in Major League Baseball, Wrigley Field is more than worth an afternoon visit. Take in a game during the Cubs’ wildly successful season or go on an after-hours tour behind the scenes to soak in the park’s grandeur.

Wrigley Field, courtesy of Wikimedia Commons

Wrigley Field | Courtesy of Wikimedia Commons


Get on a Boat

Lake Michigan is a gorgeous place when it’s not half-frozen. Take advantage of the deep blue waves by trying one of many different boat tours on the lake. You can also take an architecture boat cruise through the Loop on the Chicago River or rent kayaks and make your own path.

Tour a World-Class Museum

Chicago has all your culture needs covered. The downtown ‘museum campus’ includes The Field Museum, the Shedd Aquarium and the Adler Planetarium and is a terrific place to lose an afternoon (or several). Don’t forget to stop at the Art Institute, the Museum of Contemporary Art and head south for the Museum of Science and Industry. For something a bit more quirky, check out one of Chicago’s many unusual museums or, if you’re on a bit of a budget, check out our selection of the ten free museums and attractions in Chicago.


What to Eat

Classic Chicago cuisine comes down to three main food groups, and you have to try at least one, if not all three, during your visit. And, after dinner, why not check out one of Chicago’s beautiful rooftop bars and unwind under the stars with a refreshing drink or cocktail?

Giordano's deep dish pizza, courtesy of Wikimedia Commons

Giordano’s deep dish pizza | Courtesy of Wikimedia Commons

Deep Dish Pizza

Every Chicagoan has a different favorite spot for the perfect slice, and they’re always ready to defend it to the death. Giordano’s  and Lou Malnati’s offer the most downtown locations, which means they are often overrun with tourists and hyped a little higher than they can deliver. Altogether, they’re definitely a safe and tasty bet for deep dish. But if you’re looking for a tad more authenticity and respect from the local pizza connoisseurs, check out Pequod’s, Pizzeria Uno  or Gino’s East.

Chicago-Style Hot Dog

Leave your ketchup at home, people. The Chicago-style dog is famous for being messy and overloaded with condiments and, just like pizza, everyone has a strong opinion on whose is best. For reference, a Chicago-style includes an all-beef hot dog on a poppy seed bun with mustard, relish, onion, tomato, pickle, sport peppers and celery salt. For a solid option, try Portillo’s – where you can also grab a beef sandwich and mouth-watering chocolate cake shake. Other famous favorites include Superdawg, The Wiener’s Circle and Downtown Dogs. 

Italian Beef Sandwich

Outside the area, a lot of people don’t quite understand what a beef sandwich is, though it’s been a fixture in Chicago’s old Italian neighborhoods for decades. Thinly shaved beef, peppers, giardiniera and gravy on a bread roll make up this classic sandwich. Different variations are popular, and you can typically order it dry or wet/dipped, depending on how juicy you want it. Again, Portillo’s is a great option for all your Chicago cuisine needs. But try making the trek down to Little Italy for the original Al’s #1 Italian Beef (and all the other delicious authentic Italian food in the neighborhood) and your taste buds will definitely thank you. Other good options in the Loop are Mr. Beef and U.B. Dogs


Where to Stay

Downtown Chicago has its fair share of luxury hotels that will offer you unparalleled city views and accommodations of a lifetime. But they’re not always an option to the average traveler. If you’re sightseeing on a budget, try the Red Roof Inn just off the Magnificent Mile, Travelodge Hotel or ACME Hotel Company. Remember that the closer you are to the city center, the more expensive your accommodation will be. Chicago’s public transit system travels far and wide to easily get you to all the best attractions.

Chicago's Loop, courtesy of Wikipedia

Chicago’s Loop | Courtesy of Wikipedia