Chicago often plays second fiddle to more popular destinations like New York City, Los Angeles, or even Miami when travelers are planning a visit to an American Metropolis.

One of Chicago’s many nicknames is actually “The Second City”, although this is possibly for another reason

America’s coastal cities or National Parks might come across as a more enticing place to visit, but Chicago has just as much to offer.

Laid back West Coast attitude is perfectly balanced with East Coast character, and as the unofficial Capital of the Midwest there is an overflow of Middle America charm and hospitality.

Three days in Chicago is just enough time to see what this place has to offer.

Crown Fountain at Millennium Park


The Loop is the ideal place to begin exploring Chicago. It’s a downtown Central Business District that’s defined by an elevated train system connecting all city districts. A large working population means that there are many options for a quality breakfast, but an Italian Beef Sandwich is a Chicago classic and should not be missed.

This area is home to some thought provoking pieces of public art; two of the most impressive are the Buckingham Fountain and Cloud Gate, a shiny sculpture that’s more popularly known as “the bean”.

Tourists by Cloud Gate in Chicago

Grant Park and Millennium Park are the hubs of downtown outdoor activity and there’s always something worth checking out; from major music events like Lollapalooza or the Chicago Blues Festival to more casual movie nights and food truck pop-ups.


Since the 19th Century until modern times, Chicago has always been known for tall buildings. Exploring the city is best enjoyed when you have an understanding of how the streets are lined with skyscrapers that all have their unique story.

Chicago Skyscrapers including Willis Tower

Options exist for boat tours and paid walking tours that focus on Chicago’s architecture, but exploring downtown Chicago on foot offers the most freedom and flexibility and gives you the option to go in any direction that you want.

North of the Chicago River, the Magnificent Mile is a scenic walk that’s a bit touristic but still remains as one of the top things to do in Chicago because it’s so convenient. Walking along this shopping focused area leads to Oak Street Beach.

This already beautiful stretch of coastline becomes even more impressive when considering how far North of the Caribbean, and far away from the ocean this beach is. The beauty and the backdrop of the towering Chicago skyline give Oak Street Beach enough personality to be considered a bucket list beach.

Oak Street Beach in Chicago

Just south of Oak Street Beach is Navy Pier, a great place to end the first day in Chicago. The Ferris wheel is an important part of Chicago’s heritage and an iconic element in the city’s distinctive skyline.

At night, it looks especially beautiful when lit up. Navy Pier offers many dining options, but fried chicken from a nearby spot like Harold’s Chicken Shack is an option that allows you to experience some of the best fried chicken in the world along with interesting extras like deep fried gizzards and livers.

Original Ferris Wheel at Navy Pier in Chicago


The second day in Chicago goes even further North. The coastline that lines Lake Michigan becomes more rustic and the buildings change from skyline to suburban as you move Northward.

The Northbound Red Line train leads to some of the trendy uptown neighborhoods and one of the stops includes the home of the Chicago Cubs; Wrigley Field.

The area around the stadium includes dedications to some of the Cubs who won them their World Series titles or helped them become one of the most popular baseball teams in the world.

Amazing Asian food can be found further North at Argyle. The lack of an obviously Oriental name like Little Tokyo or Chinatown means that this entire area is almost a secret spot.  Menus in Vietnamese or Chinese, and locals lined up to enjoy steaming hot noodles is the only assurance that these restaurants are authentic.

Beyond just Asia, quality ethnic fare includes a few affordable Ethiopian Eateries, the steadfast neighborhood taquería and a hot dog restaurant that marinates sausages in Guinness before adding it to a classic Chicago Style Hot Dog with mustard, pickles, celery salt and diced tomatoes.

The restaurant is run by the protégé of a Chicago Street Food legend that has appeared on the Food Network and Parts Unknown. Some of the more interesting hot dogs include a duck sausage that topped with fois gras and truffle aioli, and a bison sausage that’s paired with Chipotle sauce and Asiago cheese.

Hot Dog with Foie Gras and Truffle Aioli

A major highlight of this part of town is the Malt Row; an area that happens to be the home of the greatest concentration of micro-breweries. The distance between these breweries may be small, but the diversity of their brewing methods and beer styles is vast.

Craft Beer Tour in Northside Chicago

Included in the Malt Row is the first brewpub to earn a Michelin Star, an American Craft Brewer who sticks to European brewing methods and many other craft beer companies with their own unique story. Begyle Brewing and Half Acre Beer Company both stand out for interesting limited edition beer releases, and having great session beer that’s always on tap. Craft beer, a plethora of dining options, and a cool community makes Uptown Chicago the perfect place to end the day.


Like every other major metropolitan area, Chicago is home to world class museums and art galleries. One such place is the Art Institute of Chicago, one of the leading fine arts institutes in the United States. Over 5000 years of human artistic expression exist within its 11 curated departments, from Ancient Etruscan and Egyptian Sculptures to Modern art and Photographs.

The museum is known for some of the most iconic images in American Art like Nighthawks, American Gothic, and Rip Van Winkle.

American Gothic by Grant Wood

The Field Museum located further South is also home to some noteworthy exhibits, Sue the t-rex is the most extensive and best preserved specimen of one of the most well-known species of carnivorous dinosaur. Together with other exhibits like a three million year old hominid, and a giant sloth, they tell the story of life on earth.

The nearby Museum Campus is home to two other interesting institutions. The Adler Planetarium is dedicated to the study of astronomy and astrophysics and the first of its kind in the United States. The Shedd Aquarium is the first inland aquarium with a permanent saltwater fish collection. Both have interesting exhibits and interactive experiences that transport you to distant worlds; outer space and the depths of the ocean.

Carl Akeley's Fighting African Elephants

Standing on the top floor of one of the buildings that contributes to Chicago’s skyline is also something that you need to do while in the City.

Just like with the museums, there is more than one option for visiting a Skyscraper in Chicago.

360 Chicago is located at the John Hancock Building, 1000 feet above the magnificent mile. On a clear day, Lake Michigan merges with the distant blue sky and the nearby states of Michigan and Wisconsin can be seen.

Skydeck Chicago is at the top of what was until recently, the tallest building in the Western Hemisphere. The views may be less spectacular, but the coolness of The Ledge more than makes up for it.

Aerial view of Chicago and Lake Michegan

Taking in expansive views of Chicago is the perfect place to dwell on life or even just dwell on how to spend the final night in Chicago. Options include Adler After Dark, revisiting Malt Row or Navy Pier or taking one of many free walking tours that explore the food scene one of the city’s ethnic neighborhoods.

Jay Pritzker Pavilion in the Evening

Whatever you decide, do not miss out on a chance to feast on classic Chicago deep-dish pizza for dinner either before or after. The combination of a buttery crust, seasoned sausages, fresh mozzarella and sweet yet tangy tomato sauce is uniquely Chicagoan. It’s the perfect dinner to end three days in Chicago.

Lou Malnati's Pizza and Samuel Adams Fat Jack Double Pumpkin Ale