Chicago Travel Tips

Chicago is undoubtedly one of the most popular travel destinations in the USA. And it's no wonder: The city has something to offer for everyone, whether you're looking for world-class restaurants, hotels, and entertainment or fascinating neighborhoods.

In fact, Chicago has been voted the best large city in the USA multiple times by readers of Condé Nast Traveler. So if you're on the lookout for an exciting city trip, you can't go wrong with a trip to the Windy City. I've been here twice and love Chicago.

If you're planning a trip to Chicago, you'll find many useful tips and information in our ultimate travel guide to make the most of your visit. From the main attractions to insider tips on where to eat and drink deliciously, we have everything you need to know about the Windy City written down here.

Here we have listed 16 things you need to know before your visit to Chicago!

Enjoy reading our Chicago tips!

Chicago has 8.9 million residents, making it the third largest city in the USA. The metropolis is located on Lake Michigan in the state of Illinois. Chicago is nicknamed 'The Windy City' because there is always a breeze.

The most famous sports teams are the Chicago Bulls (NBA, basketball, with the legendary team around Michael Jordan), the Cubs and White Sox (MLB) baseball, and the Chicago Blackhawks (NHL, hockey).

The ideal months to visit Chicago are the summer months from June to September, when the weather is pleasant and the sun shines all day. The temperatures here are just right and a pleasant breeze blows. The water temperature of Lake Michigan also rises during this time to up to 21 degrees - perfect for a refreshing dip.

However, it can also get quite crowded during this time. Hotels are more expensive and lines at the attractions are often long.

Therefore, we visited Chicago for the first time in October. When the leaves slowly turn yellow and orange, you get stunning colors in the city. On my second visit, I was here in June, and then again at the end of the round trip around the Great Lakes in July. The temperatures were summery, but always with the typical wind that is a constant in Chicago. It makes summer pleasant.

Dom was in Chicago in Winter. It was cold, but the views were much clearer than in summer.

Chicago's climate is classified as continental, meaning it has hot summers and cold winters. Since the city is located in the Midwest, it can experience severe weather events like tornadoes and snowstorms. Nevertheless, Chicago is a great place to visit year-round. In summer, you can enjoy the many festivals and events in the city, and the autumn leaves provide a beautiful sight. No matter when you come, you will surely enjoy your time in Chicago.

Chicago is made up of 77 different neighborhoods, each with its own character. You should explore as many as you can. The majority of downtown Chicago consists of the neighborhoods of Near North Side, Near South Side, and The Loop. In the Loop, you'll find the most architecturally interesting buildings, such as the AON Center, Willis Tower, and City Hall.

In the Near North Side, there are many of the city's best restaurants, bars, and nightlife. In the Near South Side, you'll find most of the museums and cultural attractions. Whatever you're looking for, you'll find it in one of Chicago's neighborhoods.

Also interesting is the Pilsen neighborhood, known for its many Mexican restaurants, street art, and as an artist enclave. The West Loop is the culinary hotspot where we also did our food tour.

The Magnificent Mile, with its luxury boutiques and fine dining. And Wicker Park, the hipster district with many art galleries, trendy cafés, innovative restaurants, and vintage shops. Most of its Victorian buildings have been beautifully restored over the years and transformed into elegant penthouses and apartments. In Ukrainian Village, you'll find beautiful Eastern European charm, which we love.

Of course, there are numerous sights in Chicago. Even more than we all have time to visit on a single city trip. That's why I have written a detailed article about the best attractions in Chicago and here our itinerary for 4 days in Chicago.

No visit to Chicago would be complete without checking off some of the city's most famous landmarks and attractions. From world-renowned museums to iconic skyscrapers, there's plenty to entertain you.

Here are just a few of the must-see attractions in Chicago:

For tourists, there are three city passes in Chicago that require a one-time payment, allowing you to visit the included attractions. Buying one of these passes in advance can really pay off.

City cards are not always worth it. Therefore, I will give you tips on how to check if one of the passes is worth it for you.

Think ahead regarding which attractions and tours you would like to visit during your Chicago trip.

List roughly what the entrance fees for these attractions or tours would cost. Compare the prices with the Chicago CityPASS and Go City Chicago Pass.

Which pass makes sense depends certainly on the duration of your stay and your choice of attractions. We tested both passes and would claim that the Chicago CityPASS was more worth it. We were advised to take the architecture cruise with Chicago's First Lady Cruises, so the Go City Pass (different provider) was not worth it. We will be writing a detailed test report.

Passes are generally cheaper online. With the Chicago CityPASS, there are almost always discount offers. Prices on-site are usually higher, so be sure to book the pass in advance on the official website. You will then receive an email with a QR code or can store the pass in your smartphone's wallet.

Chicago is famous for its two premier observation decks - 360 Chicago and Skydeck Chicago. Both offer stunning views of the city skyline and make it difficult for visitors to choose one. That's why we visited both and even booked the option "Dinner on the Ledge" at Skydeck Chicago, which we obviously took advantage of. Deep Dish in a glass box overlooking night-time Chicago is unbelievably beautiful.

The highlight at Skydeck is "The Ledge," four glass boxes to catch a direct look down, while the adrenaline kick at 360 Chicago is "TILT," glass boxes that tilt forward giving you the sensation of looking straight down. I cannot say which view was better. During the day at Skydeck, we had a cloudy day, but during our visit to 360 Chicago, it was slightly better, yet still not with a blue sky.

Both observation decks have their merits. If you have time, you should visit both. Both platforms are included in the Chicago CityPASS and Go City Chicago Pass, so it's worth doing and you can save money when purchasing the pass.

Chicago is THE 'Foodie City' of the USA. But what is Chicago particularly famous for? Deep-Dish Pizza: The pizza made of multiple layers of cheese and sauce. If that's not enough for you, you can also add fillings like meatballs, salami, or mushrooms. More like cake than pizza and much tastier than you might think (but not comparable to real Italian pizza). We tried this at Giordanos, Pizzeria Uno (right next to our hotel), and Pequods.

Then there's the Italian Beef Sandwich (Al's #1 Italian Beef) or a Chicago-Style Hot Dog (the best ones were at Portillo's). It's not a classic hot dog, but really unbelievably good and different from what we're used to. The most important thing: No ketchup!

By the way, Chicago also has Shake Shack, the burgers known from New York are also excellent in Chicago if you're in a hurry.

In addition to these classics, there are also emerging vegan restaurants like Althea or Kale my name. Oh yes, the popcorn from Garrett Popcorn is praised and mentioned everywhere. Tastes better than it sounds: the cheese-caramel mix we tried.

Also worth mentioning is the Broken Shaker bar in our Freehand Hotel. Here you can enjoy fantastic cocktails and order small snacks. Our favorites were the Truffle Flatbread and Chicken Wings.

All my tips for the best restaurants & cafés in Chicago will soon be detailed in our Chicago Food Guide.

Many business travelers, events, and tourists drive hotel prices up. As a result, accommodations are very expensive.

Therefore, the best time to visit is on weekends. Overnight prices are a bit cheaper then. Be sure to check in advance if a major fair or festival takes place around that time, as this can also drive prices up and most hotels will be fully booked.

Are you in Chicago for the first time? Then the best location for accommodation is around The Loop. It is located in the heart of the city. Here are my four hotel recommendations, all of which we have tested:

LOOKING FOR A HOTEL?

For finding a good hotel, we recommend the platform Booking.com. We always book our accommodations on this platform or directly with American Express, as we get additional discounts with the American Express Platinum Credit Card (see details, only worthwhile for frequent travelers).

Many airlines (including Lufthansa) fly directly from Germany to Chicago. Therefore, it is worth comparing prices and booking early. I always first check Kayak to later check directly on the airlines' websites if flights are cheaper. The first time we flew to Chicago from Munich with Lufthansa.

On the last trip, we traveled very comfortably from Stuttgart via Berlin to Chicago with KLM through Amsterdam. I like the airline, and the personnel is incredibly friendly. On the return flight, we even arrived 30 minutes early in Amsterdam.

Most flights from Germany land at Chicago O'Hare International Airport. From here, you can reach the city center in about 30 - 60 minutes (depending on the time and traffic; there is always heavy congestion). You can either get to downtown with UBER or Lyft or take the train to arrive at the hotel cheaply and quickly.

Chicago O'Hare Airport is about 29 km from downtown (The Loop). Depending on the time of day, you should plan on at least 30 minutes to 1.5 hours. The John F. Kennedy Expressway is always congested.

Thus, the best way is by train. It is always the simplest and most convenient option.

The first and fastest option is to take the CTA Blue Line train. The blue line operates from O'Hare Airport directly to downtown Chicago. Although trains are an efficient form of travel, they can be very crowded during rush hour. If you want to avoid crowds, you should consider another mode of transport.

Are you not alone but traveling with several people? Then a private transfer is also worth it. We like to use UBER and Lyft for this. Generally, they are cheaper and more reliable than public taxis. Our UBER ride has consistently cost between $70 and $90, and the ride took between 30 and 45 minutes. You can also book a private driver through Get Your Guide. This can be beneficial if there are at least three of you or you're arriving during peak times.

The ride takes about 30 minutes with little traffic. During rush hour, it can often take twice as long (up to 90 minutes).

You can also get reasonably priced transport from the airport to downtown with the CTA bus. However, it takes about the same time as a car (often longer), so I've never considered this option.

Are you starting a road trip along the Great Lakes, Route 66, or heading south to New Orleans? This is the most convenient option, but not recommended. There are hardly any parking spaces in the city, and when there are, they are very expensive. Use option 1 or 2 and pick up your rental car only when leaving the city. That's what we did on both road trips.

LOOKING FOR A RENTAL CAR?

For finding a rental car, I recommend the platform check24 or Cheap Rental Car. I also compare prices with Sunny Cars.
-> Find tips for booking a rental car here. -> Don't have a credit card? Then read here how to get a rental car without a credit card.

You can comfortably reach most attractions on foot or by bike.

The Chicago Transit Authority (CTA) is the public transit system in Chicago, which includes buses and trains. The best way to get around the city is with the CTA. You can purchase a CTA card to facilitate the use of the public transport. You can also download the Ventra app, which allows you to see bus and train schedules, as well as purchase CTA tickets.

Of course, there's also UBER and Lyft if you need to cover further distances. Here you should always compare prices in both apps. Depending on the time, one app may be cheaper than the other.

Chicago is a city that you can explore wonderfully on foot. The center is quite compact. You can reach the most important places and sights on foot.

Alternatively, you can rent bikes almost everywhere in Chicago to explore the city along the beaches and the Riverwalk (Lakefront Bike Trail). You can either use the Lyft app or download the Divvy app for Chicago. The principle is similar to E-scooters here. Scan the code, unlock the bike, and go. Return at the next station and pay only for the time you used it. Note: E-bikes are more expensive than regular bikes.

We enjoyed biking along the Riverwalk by Lake Michigan. Alternatively, E-scooters are also available everywhere.

You should reserve tickets for tours in Chicago in advance. The observation decks Skydeck and 360 Chicago are very popular, as are gangster tours or architecture tours by boat.

Want to catch a basketball or hockey game? In that case, you can also only get affordable tickets long before your trip.

Otherwise, we check Get Your Guide to reserve tickets for popular sights ahead of time so we can print them or load them onto our smartphones. This way, we can avoid the stress of standing in line during our trip.

In general, people drive less aggressively and frantically in the United States than in Europe. Distances and speeds are measured in miles. One mile is about 1.609 km.

On highways, the speed limit is usually 65 mph (miles per hour, equivalent to about 104-121 km/h). In towns, it's 25 - 35 miles/hour.

Pay attention to the fact that traffic lights are always on the opposite side of the street. This can be confusing for some at the beginning of their trip.

At stop signs, be aware of the addition '4-way-stop'. Whoever reaches the intersection first goes first. Right before left does not apply here.

However, you may turn right on a red light unless there is a car from other directions (or pedestrians crossing). Only with an explicit no-turn-on-red sign is it prohibited.

Pay attention to the curb's color designation. If it's red, you shouldn't park there. You risk being towed.

Note: For renting a car in the USA, a valid German driver's license is sufficient. We always bring along our international driver's license. It helps with any issues or police checks.

To rent a car in the USA, you must be at least 21 years old. For those under 25, a higher fee applies or additional insurance must be purchased.

It's sensible to book your rental car in Germany before the trip. In case of damage, you can speak German over the phone and have a contract in your native language. We consistently have good experiences with Sunny Cars.

LOOKING FOR A RENTAL CAR?

For finding a rental car, I recommend the platform check24 or Cheap Rental Car. I also compare prices with Sunny Cars.
-> You can find tips for booking a rental car here. -> Don't have a credit card? Then read here how to get a rental car without a credit card.

Before your trip to Chicago, you need to take care of your ESTA. ESTA stands for 'Electronic System for Travel Authorization' and is the electronic system for travel permits. It is your electronic entry permit for the USA.

Here we have written a step-by-step guide for your ESTA visa.

If you're wondering how and whether to bring cash to the USA, we have the answer: You shouldn't bring any. There are credit cards that allow you to withdraw cash in local currency without paying fees. Or you can pay locally in US dollars without incurring fees either.

In short: You don't need cash in the USA anymore, and you can pay for everything with a credit card, including tips.

Continue to my tips for the best credit cards for USA travel

The best credit cards for the USA in 2025 are the Genial Card (Hanseatic Bank), the MasterCard from TF Bank, and the Debit Card from DKB Bank. With these cards, you can withdraw money from ATMs for free and pay on-site without incurring foreign transaction fees! Make sure you have at least 2 of these mentioned cards.

For the USA, I recommend the American Express Platinum (my review with everything important), as you can use it for payments everywhere, receive upgrades and late check-outs in hotels, insurance for rental cars, and a secondary driver included, while also earning points.

Before my trip to Chicago, I bought the following travel guides:Travel Know-How CityTrip Chicago: Guide with city map. It was the most recent guide available after COVID. The guide is compact and reveals to you the essentials you need to know for a visit of a few days. And it's not just valuable tips for the city with all the sights and highlights but also interesting stories and tips for restaurants and other special places.

If you don't mind the English language, you should also check out the Lonely Planet Pocket Chicago (Pocket Guide). It is ideal if you are only visiting Chicago.

We were in Chicago for four days. We spent about 80-150 Euros a day (including tours) and certainly could have traveled cheaper if we wanted to. But only eating fast food in Chicago? No, the local food is just too good. We also visited a few bars to listen to musicians and enjoyed some beer and cocktails.

In short: We treated ourselves well and enjoyed our stay.

Here, I've listed some of my expenses (I will update this as I will be there again in June-July):

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