24 hours in Chicago

Home to the 2016 World Series champions and the deep dish pizza, ‘Windy City’ Chicago is the global capital of architecture and one of the most important business centers on the planet. With 2.7 million residents in the city itself, and almost 10 million in its metropolitan area, Chicago is the third-largest city in the United States. Located along the Lake Michigan, it has been an international hub for transportation and commerce since the 1800s.

After being established as a city in 1837, it quickly turned into an industrial capital with the creation of the Illinois and Michigan canal in 1848 and the completion of a railroad network soon after that. Its architectural growth was equally as important; the city was home to the world’s first skyscraper, a ten-story home insurance building completed in 1885.

Must Experience

Cloudgate – “the Bean”

As mentioned above, Chicago is home to its own blues genre. It is therefore imperative to stop at Kingston Mines, the world-famous blues venue, located in Lincoln Park.  If your music cravings are still not satisfied, stop at the Green Mill in Uptown, the oldest jazz club in the United States and gangster Al Capone’s main hangout spot back in the 1930s.

Must Visit

Downtown Chicago offers a variety of activities that will keep you busy the entire day. To learn about the history and architecture, take the Architecture River Cruise, offered by the Chicago Architecture Foundation. It will take you on Lake Michigan and along the river for an all-inclusive skyscraper viewing tour. After that, stop at the John Hancock Center and go up a 1000 feet to get a 360 degree view of the city. The observation deck also offers the ‘Tilt’ attraction, a platform that will tilt you out from the 94th floor.

From the John Hancock Center, walk along the ‘Magnificent Mile’. This is an upscale shopping avenue full of historic landmarks. From there, you will reach Millennium Park and Grant Park. These parks are home to the famous Cloud Gate (‘Bean’) but also to the Jay Pritzker Pavilion, the Art Institute of Chicago and the Buckingham Fountain. During the summer many events take place in the park, such as movie screenings and concerts by the Chicago Symphony Orchestra.

Must Watch

Navy Pier Ferris Wheel

Chicago has five professional team sports. These include the Chicago Bulls (basketball), the Chicago Bears (football), the Chicago Fire (soccer), the Chicago Blackhawks (ice hockey), the Chicago White Sox and the Chicago Cubs (baseball). The latter won the 2016 World Series Championship, and you can catch one of their games alongside thousands of proud Cubs fans at the Wrigley Field.

Chicagoans are also very proud of their stand-up comedy scene.  The city hosts various comedy clubs that include improvisation, stand-up comedy, open mic, sketch, theater and more. Many famous comedians such as Steve Carell, Jim Belushi, Stephen Colbert and Bill Murray made their debuts at the Second City in Old Town.

Must eat


Not only is Chicago a global culinary headquarter, it is also famous for its legendary deep-dish pizza and Chicago-style hotdog. Pizzeria Uno is not only the place best place for deep-dish pizza (characterized by a very deep crust, resembling a pie), it apparently also originated there. The typical Chicago hotdog has onions, tomato slices, green relish, yellow mustard, pickled peppers and also a dill pickle. You can find it at Portillos in River North, in the same neighborhood as Pizzeria Uno.

Must drink


Thirsty after all that Chicago fare?  Chicago has a good history of brewing and hosts a number of brewpubs and microbreweries. The largest brewer of the region is Goose Island Brewery, with a brewpub located on Clybourn Avenue. The company produces a large number of beers that are available all year long, as well as some seasonal beers.

Must stay

Navy Pier

The Palmer House Hilton has been an architectural wonder since it first opened in 1871. With its extraordinary ceilings and majestic chandeliers, this hotel has long been a part of the National Trust for Historic Preservation. Located in downtown Chicago, the hotel is also close to trains, busses and most of the city’s touristic attractions. If you can’t afford this hotel, or would rather stay somewhere else, make sure to still stop by the bar, the interior design of this place is incredible!

When to go:

Planning a visit?  Chicago winters are harsh, reaching temperatures of -30F. The best time to visit is in the summer, between May and September, when most attractions are open.

Getting there:

View of the Willis Tower

Plane- Chicago has two airports, Chicago O’hare Airport  and Chicago Midway Airport.

Train- Amtrak trains arrive at the Union Station in downtown Chicago.

Car- Highway I-80 when arriving from East or West, I-94 when arriving from the North and I-55 when arriving from the South.

Getting around

To get around Chicago, the best way is to take the Chicago Transit Authority (‘CTA’) bus or train. Public transportation is extremely well developed in the city, connecting downtown to both airports. Fares are relatively cheap and the trains are easy to identify (by color).


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  • Medha Verma Bector

    That’s a very short and precise post about Chicago, love that you’ve listed what all can be done in a single day because many times, there are cities we do not get more than 24 hours to spend in. I have never been to Chicago but would love to go, I have some friends there and they love it.

    • Wallis

      Chicago is absolutely incredible! You definitely need more than 24 hours haha but if you don’t have that much time at least you know where to go!!

  • Ritika

    I love 24 hours post ., with full time job we all try to make best out of it and these 24 hours posts help a lot and I must say u have covered all the main spots of Chicago .. Thanks for sharing

  • ritika

    i love 24 hours posts. with limited time sometimes thats all we have to cover a city. thanks for indepth information. have bookmarked this post for our next visit.

  • Ambuj Saxena

    I think one can’t explore any place more than that within 24 hours! You have covered almost all the aspects that Chicago offers. Thank you for the precise post. I loved Chicago downtown but that was long back in 2005. I am sure a lot must have changed by now. I just had one suggestion, if you could make the pics bigger in size. I would have loved to soak in the essence of Chicago better. 🙂