Chicago: The best tips for a weekend in the Windy City

Chicago is the third largest metropolis in the United States. Nevertheless, the fewest America travelers are drawn to the city with the impressive skyscrapers and the gigantic Lake Michigan. Our author still went there and shows why the adopted home of the Obamas is so much more exciting than its reputation.

Almost 2.7 million inhabitants, gigantic architecture, food capital of the USA, spectacularly beautifully located on Lake Michigan – and yet Chicago simply does not take place on the travel radar of most America vacationers. Too long is the shadow of the other famous skyscraper sea city on the east coast, New York City. Chicago, twelve hours by car and 1,300 kilometers to the west in the state of Illinois, looks like the wrongly spurned stepsister of the megacity on the Hudson.

Chicago has a lot of what New York has to offer – and should be particularly sympathetic to those who currently categorically reject a trip to the USA because of the man switching and acting in the White House. Because: Chicago has been firmly in the hands of the Democrats for decades and even today, since Barack Obama is no longer the president and his successor successively reduces the hard-won achievements of the first African American at the head of the United States, 'Obamaland'.

Obama stronghold and Trump apathy

Obama lived and worked on the very big political stage in Chicago for 20 years before his career. Here he met Michelle, a native of Chicago, and the daughters Malia and Sasha were born here. The Chicagoers still love him today – and the new shooting star from Chicago is already in the starting blocks: Lori Lightfoot. Your biodata: female, Afro-American, openly gay.

She has been the new mayor since May. The Chicagoers and many others who believe in free and modern America celebrated after their choice. Trump raged. He is accordingly unpopular in the city.

All other guests, however, greet the Chicagoers in the typically charmingly innocent but incredibly friendly American way. Since Chicago is also incredibly large and most of the visitors know very little about the city, we give an overview of what you visit when you visit not to miss a case.

First day, in the morning

Even those who have hardly had any associations with Chicago so far Bean, or the Cloud Gate, as the artwork by Indian-English artist Anish Kapoor, which is welded together from 168 stainless steel plates and always polished to a high gloss, is something everyone has seen before. No wonder: Nothing is photographed more often in Chicago than the Wolkentor sculpture, which was completed in 2006. Running under the reflecting silver bean is therefore a must-do list for all Chicago travelers.

This is particularly good in the early morning, because then the chances of taking a selfie are entirely with the futuristic one Bean and the gigantic skyscrapers of adjacent Michigan Avenue that are reflected in it. From the morning at the latest, thousands of tourists will populate the AT&T square, all of whom also want to get a photo with the famous bean.

Then a short walk through the neighboring Millenium Park is an option. It is the largest public park in the city and something like Chicago's living room. Depending on the weather and season, concerts, open-air cinema, free workouts or events for children take place here. You can take part in many activities for free. Just have a look on the Internet to see what is currently on offer.

Exciting, but no time right now?

First day, at noon

To get a first overview of the city afterwards, a walking tour through downtown is recommended. In Chicago, this center area is also called "The Loop". This goes back to the famous Chicago ring railway, which, unlike in many cities, runs above instead of underground. The city can of course be explored on foot even better than with the clattering panoramic elevated train, whose iron rails wind on meter-high stilts between the skyscrapers and in places above the heads of passers-by.

The Chicago Greeters offer very good tours. This is not a conventional provider, but the people who have to do it best: the Chicagoers themselves. People who live here, live, know their city and like to tell about it – even so much, that they don't want money for it.

One of the volunteers is Howard Raik. Born in New York in a polo shirt, a casual sweater knotted around the waist and sports shoes with a poison green lacing have been living in Chicago for 45 years. Since 2001, he has been guiding visitors through his current hometown as part of the Greeter program. And he still likes to do it at the age of 76, as he explains. "I've met a lot of people from all over my life, it's still fun today."

The tours can put together visitors according to their own interests, pick out a certain district, book a historical tour or have the best shopping spots in the city shown. Even in German if desired, explains Howard.

While walking us through the streets of Windy City leads (that's the nickname of Chicago; this has nothing to do with the sometimes rather drafty weather, but with the windy shops that were once shot here. Chicago was the most corrupt city in the country in the 20th century), he works with his full beard and the sonorous voice a bit like the storytelling grandpa, who has a different story to tell for each building, each block of houses.

His tip away from the city center: the former working-class district of Pilsen. Located southwest of the downtown area, immigrants from Eastern Europe used to live here. Today Pilsen is home to one of the largest Hispanic communities outside of Mexico. The neighborhood is constantly changing, Howard says. For him, Pilsen is therefore one of the most interesting quarters of Chicago, as history can be observed live here, sociological upheavals, new, old and their interaction, everything is constantly changing.

When we stand in front of a brick building on a street corner next to a laundromat, Howard points to the unassuming dark brown stone facade. "Two months ago there was still a colorful graffiti that I liked to show my groups," he says. "When I was there with another group the following week, it was gone." Painted over, scraped off. That shows the dynamism in Pilsen.

If you want to get closer to Mexican art, which can also be found on the house facades, you should pay a visit to the National Museum of Mexican Art.

First day, in the afternoon

Back in the city center, the first thing to do is to relax on the Chicago Riverwalk: The promenade along the Chicago River, which eventually flows into the Gulf of Mexico, has been gradually expanded since 2001. Made pedestrian-friendly, that was the goal of the city administration. Remarkable for an American metropolis to this day.

In the past, nobody wanted to sit or stroll here, the buildings along the river were specially designed so that no window overlooked the river. The Chicago River was a single dump, a sewer that even became a health hazard in the late 19th century. Today the Riverwalk is one of Chicago places to be: beautiful restaurants and bars are lined up, in between food stalls where you can grab a snack and then make yourself comfortable in one of the deckchairs on the bank to watch the goings on and on the river. Framed by spectacular buildings.

Very prominently located on Michigan Avenue: the Trump Tower. Despite the pronounced apathy of the Chicagoers towards their current president, the real estate billionaire had a gigantic 423-meter tower in the city center before his political career, which mainly houses offices and apartments. When he was just a rich investor, nobody cared. Today the tower is a thorn in the side of many Chicagoers. However, it still has an impressive appearance to this day.

If you are more interested in the architecture of the city and the stories behind the towers and steel castles: The Chicago Architecture Foundation offers informative and humorous tours (duration: about 1.5 hours, price: not cheap, $ 45 per person, more information here).

Less facts, but a very special experience: paddle through the skyscrapers in a rocking kayak. Some organizers even offer particularly atmospheric sunset tours. Absolute recommendation!

  • More information about the kayak tour: e.g. with Urban Kayaks, duration: 1 hour, from $ 45 per person, kayak rental without a guide a little cheaper,

First day, in the evening

For dinner it goes to the Pizzeria Uno. It is an institution in Chicago and known far beyond the city limits. Because in the shop with the red and white awnings and geometrically arranged tables like in a classic American diner there is a dish that is nowhere else in the world: the deep dish pizza. Use EXPEDIA vouchers now for attractive last-minute trips

However, the Chicago version has little to do with the original Italian pizza with little topping and wafer-thin bottom. Instead, there is a pizza several centimeters high, which is more reminiscent of a quiche and served bubbly hot from the oven. The special thing about it: the topping is arranged the other way round than with conventional pizza, that is: first cheese, then salami, ham and the like, and finally a thick layer of tomato sauce. "Otherwise the cheese will burn," explains restaurant manager Howard McHale. "Because everything is through, our pizza needs at least 45 minutes to be ready."

Whether the Chicago version of the pizza tastes better than the pizza that we know from the Italian is a matter of taste. At least everyone should try the Deep Dish Pizza once.

  • Info: 29 E Ohio St, Mon-Fri 11 a.m. to midnight, Sat to 1 a.m., Sun to 11 p.m.,

First day, late at night

If you still have energy, you should go up to the 104th floor of the Willis Tower. The elevator ride also takes only 60 seconds. Once at the top, you can not only see impressive tall houses (Chicago is considered the birthplace of the modern skyscraper), but you can test your head for heights on a glass platform suspended 412 meters above the streets.

That's what counts: 1.5 million people from 150 countries made the "Skydeck" the second most popular attraction in the city after the Shedd Aquarium last year. General tip: there is less going on in the evening than during the day. For those who have the Chicago Pass, there is also a separate entrance so that you can simply walk past the normal queue.

Savings tip: Chicago City Pass

If you want to see and visit a lot, the Chicago City Pass is worth it. This includes admission to the Skydeck, Shedd Aquarium, Field Museum and optionally to the Art Institute or the Adler Planetarium, the 360 ​​Chicago viewing platform or the Museum of Science and Industry, each at a discounted price. There are also special City Pass queues at many attractions, which are often significantly shorter than the regular ones,

Second day, in the morning

Chicago is far from the sea. However, the feeling of being at the sea still exists directly behind the last front of the city: Because Lake Michigan is so big that you can't see the other bank even on clear days and equipped with binoculars, and it also in many places of Lined the beach, it feels like Chicago is on the coast.

You can relax and enjoy this atmosphere in the beach restaurant Shore Club. Located directly on the sandy beach, with stylish lounge furniture and instagram-worthy dishes that are fun for both the taste buds and the eye, the semi-open terrace restaurant is perfect for an extensive breakfast or early lunch.

  • Info: 1603 N Lake Shore Dr, daily 11 a.m. to 10 p.m., on weekends from 10 a.m.,

Second day, in the afternoon

Because it is so beautiful, it makes sense not to go back to the city after eating, but to spend a little more time at the lake. Perfect for that: a bike. Just swing on it, ride on the wide paved bike paths along the lake, stop in between, enjoy the view of the skyline and stretch your toe into the ice-cold water of the fifth largest freshwater lake in the world.

Also recommended: the guided bike tours from Bobby’s Bike Hike. On the Lakefront Neighborhood Tour, for example, the local guides show the part of Chicago that hugs the lake, the chic Gold Coast area.

There are large, ingrown avenues, houses with cast iron fences and lavish floral decorations. Overflowing hydrangeas adorn many entrance doors. Even without a lot of explanations, you understand that you have money here – and that's nice to look at if you don't have the dollars to live here yourself.

The adjacent Old Town district is also worth a visit. Between brick-built townhouses there are great shops, boutiques, bars and restaurants with terraces on the sidewalk above which fairy lights dangle. Perfect to stroll a bit through the streets and buy a souvenir or two.

Second day, in the afternoon

The afternoon is reserved for culture so that the brain also gets a little food: the range is extensive. The Natural History Museum Field is considered one of the best in the country and one of the largest in the world. If you want to see all exhibits and exhibitions, you probably need a whole day. However, only a few are enough to pay a visit to the most famous “inhabitants” of the Field Museum, such as Sue, the world's largest known fossil of a Tyrannosaurus, to visit an authentic Indian earth hut or to use 3D simulation to beam onto the Galapagos Island and rare animal species hours.

At least as worth seeing for art fans: The world-famous Art Institute with more than 300,000 works of art and culture from five millennia, including famous works such as Van Gogh's "Self-Portrait" or the oil painting "American Gothic" by Grant Woods. Both museums are included in the Chicago City Pass.

Second day, in the evening

Chicago is diverse – cultural, ethnic, and culinary. The selection of excellent restaurants in the city with the largest food festival in the world is huge for everyone. In conclusion, instead of lumpy burgers, there is typically Spanish tapas. The Cafe Ba-Ba-Reeba is one of the best addresses in Chicago. In the large but cozy restaurant, guests can try goat cheese in tomato sauce, waygu beef carpaccio with black truffle, homemade paella and scampi-filled dumplings. Be sure to test: the light mango sangria. Delicious!

  • Info: 2024 N Halsted St, Mon-Thu 4 p.m. to 10 p.m., Fri 11.30 a.m. to midnight, Sa 9 a.m. to midnight, Sun 9 a.m. to 10 p.m.,

Anyone who is still looking for a cool bar in the evening should remember Cindy’s. In the rooftop bar there are not only good drinks, but also one of the best views in the city: Millenium Park, Lake Michigan, the houses of Chicago – and right outside the door: the famous Bean. There is hardly more Chicago.

Hotel tip: Chicago Athletic Association Hotel

Built in 1893, the hotel was formerly an exclusive Athletic Member Club. Since 2015, the time-honored building has been a four-star hotel with a perfect location in the middle of downtown, opposite the Millennium Park. The sport motif still runs through the hotel today: side horses as a bench at the foot of the bed, wall bars as a desk construction, even the old basketball court still exists. It is now used as a ballroom. Be sure to reserve a room on Michigan Street. Information at:

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Note: The author was supported in her research by Choose Chicago.