Chicago: 13 Highlights & Tips for the Windy City

After New York and Los Angeles, Chicago is the third-largest city in the United States. The impressive skyline of the Windy City gives this metropolis a unique charm.
With its fascinating architecture, the scenic Chicago River, and beautiful beaches along Lake Michigan, Chicago offers an unparalleled setting.
The city's lively people embody the American Way of Life and add to its special atmosphere.

During our road trip through the eastern United States, Chicago was undoubtedly our highlight. Shortly after our arrival, we were completely captivated by the city!
To ensure that you are equally fascinated during your visit to Chicago, we’ve compiled our top 13 best tips and highlights for the Windy City.

1. THE LOOP - CHICAGO'S DOWNTOWN

Most Chicago residents colloquially refer to the city center as “The Loop”. This area is the second-largest business district in the U.S., after Midtown Manhattan, and one of the world’s central economic hubs.

The term “The Loop” originated in the late 19th century when cable cars looped around what is now a 35-block area of downtown.
As space in the heart of the city quickly became scarce, architects had to devise creative solutions. Even the increasingly taller buildings could no longer meet the demand for space.
Consequently, they converted the cable car system into the elevated railway that still exists today, known as the “Chicago Elevated”, which runs 8 meters above the street.

The historical Chicago Elevated, which rattles over numerous steel supports every few minutes, is simply known as the “L” to locals.
A ride on this famous silver elevated train is a must during your visit to Chicago. Tickets are available at every station.

THE MAGNIFICENT MILE / MICHIGAN AVENUE

A major highlight in The Loop is the Magnificent Mile. This area starts at the DuSable Bridge right by the Wrigley Building.
It’s not the official street name but rather a fitting nickname for Chicago’s most famous shopping mile.

The almost 2-kilometer-long Magnificent Mile stretches across the northern part of Michigan Avenue. Here, you'll find not only high-end designer stores but also popular clothing chains like H&M, Zara, and many more. Luxurious hotels, as well as bars and restaurants with their impressive facades, line this grand street.

A walk along the Magnificent Mile is a must. Even if you’re not interested in shopping, the stroll is worth it for the impressive architecture alone.
A particular highlight is the Water Tower Chicago, a historic building made of yellow limestone and one of the oldest in the city.

Built in 1869, the Water Tower once served as a water supply station, pumping water from Lake Michigan.
If you’d like to visit the old pumping station, you can purchase a ticket from the Lookingglass Theatre Company, which is located right in this historic building.

By the way, did you know that Wrigley’s (the chewing gum manufacturer) is from Chicago, and McDonald’s has its headquarters there?!

2. THE SKYDECK AT WILLIS TOWER

The nine interlocking square towers of the Willis Tower were the tallest office towers in the world until 1996 and, at a height of 527 meters and 108 floors, remain Chicago's tallest building. An express elevator takes you directly to the Skydeck, the observation deck on the 103rd floor.

From 412 meters above the city, on clear days, you can enjoy breathtaking views over the Windy City.
On especially clear days, you can even see into neighboring states and far across Lake Michigan.

A particular highlight of the Skydeck is the glass balconies (known as “The Ledge”) made entirely of glass. With a little courage (and ideally, no fear of heights), you can stand on one of the four glass balconies on the tower's west side and enjoy an unobstructed view of the city 400 meters below. The view is simply unmatched!

The Skydeck is open daily: from October to February, from 10:00 am to 8:00 pm, and from March to September, from 9:00 am to 10:00 pm. It’s essential to book tickets online in advance, as they have specific timed entry slots. You can book standard tickets in advance here. Entry to the Skydeck is also included in the Chicago City Pass, allowing visits both during the day and at night.

Our tip: To make the already spectacular view even better, visit the Skydeck either early in the morning shortly after opening or about 30 to 40 minutes before sunset!
If you’re there at sunset, you’ll have the chance to experience Chicago at night and take some beautiful photos.

GOOD TO KNOW

For your trip to the USA, you’ll need a power adapter, as plug types A and B are used. These are different from the plug types commonly used in many countries around the world.
You can find a suitable adapter here:  Travel Adapter USA.

3. 360 CHICAGO AT THE JOHN HANCOCK TOWER

The John Hancock Building, standing 344 meters high (459 meters to the antenna tip), is Chicago’s fourth-tallest building and houses the spectacular 360 Chicago observation deck on the 94th floor. It's considered the smaller sibling of the Willis Tower.

In addition to the observation deck, the building contains nearly 700 apartments, offices, shops, restaurants, and a television station.
Notably, it houses North America's highest swimming pool on the 44th floor of the John Hancock Tower.

If you want to experience Chicago from a different perspective than the Willis Tower, a visit to 360 Chicago is highly recommended.
Located 314 meters above ground, you’ll reach the 94th floor in seconds on one of the world’s fastest elevators.

For thrill-seekers, there’s an option to stand on the “Tilt”—a glass window that tilts outward. Like at the Willis Tower, you’ll have a breathtaking view over the Windy City.
On clear days, you can see into neighboring states and far across Lake Michigan.

The 360 Chicago observation deck is open daily from 9:00 am to 9:00 pm. It’s essential to book tickets online in advance, as they have specific timed entry slots.
You can book standard tickets in advance here. Entry to the observation deck is also included in the Chicago City Pass.

Our tip: To make the already spectacular view even better, visit 360 Chicago either shortly after it opens in the morning or about an hour before sunset (last entry time)!
If you’re there at sunset, you’ll even have the chance to see and photograph Chicago at night.

4. THE MILLENNIUM PARK

Millennium Park is Chicago's largest public park and serves as the city’s green lung.
It provides a retreat for the stressed city-dwellers and stretches over 99,000 square meters from downtown to the shore of Lake Michigan.

As Millennium Park is worth a visit in every season, it attracts up to 4 million visitors annually.
In addition to its well-maintained green spaces, the park offers numerous attractions for all ages.

From June to August, you can enjoy live music or film screenings every evening on the large open-air stage. Chicago locals and many tourists gather with blankets, chairs, snacks, and drinks to enjoy the events together. Admission to these events is free, making Millennium Park an ideal spot for relaxed summer evenings.

THE BEAN OR CLOUD GATE

Perhaps the most-photographed sculpture in Chicago and an absolute must-see for tourists in Millennium Park is Cloud Gate. This impressive stainless-steel sculpture is 11 meters long and 22 meters high and resembles an oversized bean, hence the nickname “The Bean”. To locals, this nickname is far more common than the official title.

Be sure to check out “The Bean” for yourself, as the fascinating reflections of Chicago’s skyline and the sky on its stainless-steel surface are breathtaking, especially at dawn!

In the neighboring Grant Park, which stretches south of Millennium Park, you’ll find another highlight: the Buckingham Fountain.
This artistic, gigantic fountain is a must-see and makes an excellent photo spot with the skylinein the background, both day and night.

5. THE NAVY PIER

Along the shore of Lake Michigan, you’ll find the Navy Pier, a 1,000-meter-long entertainment area built on 20,000 wooden piles.
Numerous attractions await you here, including a ferris wheel, a musical theater, a palm garden, a climbing wall, a carousel, and the Chicago Children’s Museum.
No wonder the Navy Pier is equally popular with locals and tourists.

The “Centennial Wheel”, a ferris wheel with enclosed cabins, operates year-round, allowing you to enjoy a stunning view of Lake Michigan and the Windy City even in the middle of winter.

In summer, free fireworks are displayed every Wednesday and Saturday evening. Additionally, there are many other free events year-round, such as festivals and concerts.

Besides the various attractions, the Navy Pier is also where you can catch boats for tours on the Chicago River or Lake Michigan, offering a chance to explore the city from the water.

6. A BOAT TOUR ON THE CHICAGO RIVER

Do you have tired feet from sightseeing or want to experience the Windy City from a new perspective? Then a boat tour on the Chicago River is just the thing for you!
This tour not only offers an extraordinary way to explore the city, but it is also extremely convenient.

As the boats pass impressive buildings like the Wrigley Building, the Tribune Tower, and the Trump Tower, you’ll receive fascinating information about the buildings and the history of Chicago through speakers.

The boats dock daily, rain or shine, at the Navy Pier. Depending on the chosen tour, the ride can last between an hour and an hour and a half. Prices vary depending on the tour.
You can buy your boat tickets directly at the pier, but we recommend booking your ticket online in advance through GetYourGuide to save time in line and secure your preferred tour time.

7. THE CHICAGO RIVERWALK

Cities built directly on the water hold a special charm. That’s why we highly recommend a stroll along the beautiful Chicago Riverwalk.
This modern pedestrian promenade starts at the Old Post Office Plaque at the Lake Street Bridge and stretches over 5 kilometers along the south bank of the Chicago River to Lake Shore Drive on Lake Michigan'sshore.

The entirely car-free Chicago Riverwalk spans six street blocks, each with its own unique bay, specially landscaped and designed for different activities.
To make the areas easier to distinguish, they have been given special nicknames:

• The Marina (from State to Dearborn): Here, restaurants and numerous seating options invite you to enjoy the river view with a cool drink or snack.
• The Cove (from Dearborn to Clark): In this area, you can rent a kayak or grab a small snack.
• The River Theatre (from Clark to LaSalle): An urban oasis adorned with numerous trees providing shade on hot days.
• The Water Plaza (from LaSalle to Wells): This sunny bay with a beautiful fountain invites relaxation.
• The Jetty (from Wells to Franklin): Here, you can quietly watch birds, maybe spot a fish underwater, and even try fishing.
• The Boardwalk (from Franklin to Lake): From here, you have a stunning view of the junction of the three branches of the Chicago River.

The Chicago Riverwalk offers a perfect opportunity to experience the beauty of the city while enjoying a variety of activities.

8. THE SHEDD AQUARIUM

The Shedd Aquarium was once the largest indoor aquarium in the world. While it no longer holds that title, it remains one of the most significant aquariums globally, housing around 32,000 animals. There is an impressive variety to discover in over 18 million liters of water – equivalent to about 126,000 bathtubs.
The Shedd Aquarium is divided into eight exhibit areas that showcase the fascinating underwater world from different regions of the earth:

1. Amazon Rising: Here, you’ll find a variety of tropical fish from the waters of the Amazon.
2. Caribbean Reef: This exhibit houses turtles, colorful fish, and vibrant corals.
3. Polar Play Zone: Experience the Arctic waters with penguins in their natural environment.
4. Wild Reef: Discover the Indian Ocean with sharks, stingrays, and a piece of the Philippine coral reef.
5. At Home on the Great Lakes: This exhibit shows the creatures of the Great Lakes and their unique ecosystems.
6. Waters of the World: In several small tanks, you can observe octopuses, spider crabs, and other marine creatures.
7. Abbott Oceanium: Here, you’ll encounter large marine mammals like beluga whales, dolphins, and sea lions.
8. Underwater Beauty: Admire the colorful inhabitants of the ocean floor, including crabs and small tropical fish.

With over 650 different species residing at the Shedd Aquarium, a visit is worthwhile. Plan at least two hours to half a day to fully enjoy everything on offer.

The aquarium is open daily from 9:00 am to 6:00 pm. Since the Shedd Aquarium is very popular, we recommend visiting on weekday mornings if possible.
Also, we suggest booking your ticket online in advance to avoid long queues at the ticket counter. Admission is included in the Chicago City Pass.

9. THE FIELD MUSEUM OF NATURAL HISTORY

The Field Museum of Natural History is an impressive natural history museum spanning 85,000 square meters across five floors.
It is one of the world’s most renowned natural history museums, housing one of the largest collections in the fields of natural sciences and anthropology.

A highlight of the Field Museum is the best-preserved Tyrannosaurus Rex ever found – a must-see for any dinosaur fan!
In addition to this fascinating specimen, the museum has numerous natural history treasures that provide a deep insight into our planet's history.

Since the museum offers so much, you should plan at least half a day for your visit. The Field Museum is open daily from 9:00 am to 5:00 pm.
To avoid long queues at the ticket counter, we recommend visiting on weekday mornings if possible. It's also advisable to book your tickets online in advance to save time.
Admission is included in the Chicago City Pass.

10. THE ART INSTITUTE OF CHICAGO

The Art Institute of Chicago is an impressive art museum that houses over 300,000 art and cultural artifacts spanning five millennia.
It is particularly famous for its extensive collection of French Impressionists and ethnological exhibits from America, Africa, and Asia.

To explore the entire exhibit, you should plan at least half a day. If time is limited or you’re only interested in the museum's highlights, a visit is still worthwhile.
You can check the Art Institute of Chicago’s website in advance to see which exhibitions or events are scheduled during your visit.

The museum is open daily from 11:00 am to 6:00 pm. Admission is included in the Chicago City Pass.

11. CHICAGO'S CITY BEACHES

Had enough of the city and skyscrapers? Then take a break from sightseeing at one of the beaches along the shore of Lake Michigan!

Since it’s a lake rather than a sea, it’s understandable that all the sandy beaches here are artificially created.
Nevertheless, you can enjoy a few relaxing hours here, especially in good weather.

Just a short distance from downtown, you’ll find Ohio Street Beach in Olive Park, ideal for a quick visit. If you’re looking for more space and a nicer view, Oak Street Beach and North Avenue Beach in the city's north are excellent alternatives. These beaches are especially popular with locals and tourists alike in the summer.
Here, you can sunbathe, swim, or just enjoy the atmosphere.

A visit is particularly worthwhile in the late afternoon. Then you can relax in one of the beach bars and enjoy a sundowner with the locals.

12. VISIT A ROOFTOP BAR

One thing’s for sure: We love rooftop bars! The combination of delicious drinks, chill music, and a relaxed atmosphere with a breathtaking view of the Windy City’s lights makes the first evening in Chicago an unforgettable experience.

There are plenty of rooftop bars in Chicago that you should visit. Some of the best include RAISED, Terrace 16, Cerise Rooftop, Utopian Tailgate, and Gene’s Rooftop Beer & Wine Garden. Everywhere you go, you’ll be able to enjoy the spectacular views of the skyline and Lake Michigan.

Please note: You must be at least 21 years old to visit rooftop bars.

13. WANT EVEN MORE SHOPPING?

Was Magnificent Mile not enough? Craving more shopping? Then you should check out the Chicago Premium Factory Outlet, located about 35 minutes from the city by car.

Factory outlets in the USA are similar to large, modern shopping malls or small shopping villages with lovely parks, restaurants, and various shops. What makes these outlets special is that you can buy many items from big and well-known brands at unbeatable prices – a real advantage compared to prices in many other parts of the world.

The Chicago Premium Outlet is one of over 1,000 factory outlets in the USA, mostly operated by Tanger or Simon. Here, you’ll find a wide range of well-known designers and brands, including Adidas, American Eagle, Boss, Burberry, Columbia, Calvin Klein, Dior, Coach, Converse, Diesel, Fossil, GAP, Guess, Lacoste, Levis, Michael Kors, Nike, Polo Ralph Lauren, Puma, Reebok, The North Face, Timberland, Tommy Hilfiger, Under Armour, VANS, and many more.

TIPS FOR SAVING MONEY WHEN SHOPPING AT OUTLETS:

1. Get the coupon booklet: Visit the information counter at each factory outlet and get the in-house coupon booklet for many attractive discounts.
2. Join the customer club: Register online for the customer club of each factory outlet. Membership is essential in the USA if you want to save money.
   Even for a one-time visit, it’s worth the effort, as you’ll gain access to exclusive coupons.
3. Subscribe to the newsletter: Sign up for the outlet's online newsletter shortly before your visit. You’ll often receive a welcome coupon for 10% to 20% off in various stores.

Outlets usually have a pleasant atmosphere with fewer people, so you can shop at leisure. The good selection of products and ample parking options make shopping a pleasure.
Be warned, though: you might end up doing a lot of shopping!

Important note: Remember that sales tax is not included on U.S. price tags. It’s only added at checkout.
So don’t be surprised if the final price is higher than the one on the tag – it’s typically just the tax.

IS THE CHICAGO CITY PASS WORTH IT?

In short: Yes, the Chicago City Pass is worth it, especially for first-time visitors spending more than a day in the city.
Our sightseeing included attractions like the Skydeck in Willis Tower, 360 Chicago in John Hancock Tower, and the Shedd Aquarium.

Entry fees for these attractions alone would currently total around $130. With the Chicago City Pass costing $128, it’s a great deal when you compare the combined entrance fees.

The City Pass includes:

• Shedd Aquarium – fixed
• Field Museum – fixed

Plus, you can choose three of the following five attractions:

• Skydeck Chicago
• 360 CHICAGO Observation Deck
• Art Institute of Chicago
• Museum of Science and Industry
• Adler Planetarium

The Chicago City Pass is valid for 9 days from first use. After booking, you’ll receive the pass via email, which can be used directly as a mobile ticket.
Book the Chicago City Pass online at getyourguide.

THE BEST TIME TO VISIT CHICAGO

You can, of course, visit Chicago all year round, so the best time to go depends on your personal preferences.

The city has a continental climate, meaning summers can be hot, while winters can be very cold.

The ideal travel times are between the end of April and October. During these months, you can generally expect pleasant weather.
By the end of April, daytime temperatures reach around 15 °C. From June to September, you can even enjoy average temperatures of about 27 °C.
After these months, temperatures drop significantly again.

The winter months in Chicago are often extremely cold and uncomfortable. The high humidity can intensify the cold, making the winter months and parts of spring especially challenging.

It’s wise to be prepared for all weather conditions in Chicago. In just a few days, the weather can shift from very windy and rainy to a heatwave.
During our visit in late April, we first enjoyed summer-like temperatures, only to be surprised by heavy rain and a sharp drop in temperature the next day.

By the way: Chicago earned the nickname 'Windy City' not only because of the strong winds that sweep through the city, but also due to its reputation in the late 19th century for boastful politicians and exaggerated claims, particularly around the time of the 1893 World’s Fair.

THE IDEAL LENGTH OF STAY IN CHICAGO

The ideal length of stay depends, like the best travel time, on your personal preferences. We recommend planning for 3 to 5 full days.
This timeframe gives you ample opportunity to explore the main sights and fully immerse yourself in the exciting atmosphere of this metropolis.

Of course, it’s also possible to discover Chicago in just 1 to 2 days. However, this may result in rushing from one attraction to another and potentially missing out on interesting places – which would be a real shame!

With 3 to 5 days, you can make the most of your visit and build a deeper connection with the city.

HOTELS & ACCOMMODATIONS

Admittedly, finding the perfect place to stay in a metropolis like Chicago isn’t exactly easy. There’s no shortage of hotels and other accommodations, but one thing they all have in common is that they’re not exactly cheap. Whether it’s a hotel, hostel, apartment, or another type of accommodation, you’re sure to find the right place for you on platforms like booking.com or Airbnb.

We made a very good choice with our accommodation at the Best Western Hotel on the southern part of the well-known Michigan Avenue across from Grant Park.
The location and value for money were excellent, making it an ideal starting point for exploring the city entirely on foot.

Planning a road trip through the USA? Then you might find our following posts interesting:

• Washington D.C.: 12 Must-See Sights in the U.S. Capital
• Washington D.C.: The Best Tips for Your Trip
• New York City: 15 Sights You Must See
• New York City: The Best Tips for Your Trip

Enjoy browsing and planning!

USEFUL LINKS & RECOMMENDED TRAVEL GUIDES FOR YOU

• The Right Travel Adapter for the USA
• Find affordable rental cars at rentalcars.com
• Find affordable flights at skyscanner.com
• Discover the best accommodations
• The Chicago City Pass
• The Best Travel Guides for Chicago
• Unique Excursions to Experience in USA

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Note: This blog post contains our personal recommendations in the form of so-called affiliate links. If you book or purchase something through these links, we earn a small commission. There is absolutely no change to the price for you.