Highlights of Chicago in 4 Days

Attractions in Chicago in 4 Days: Our Suggested Itinerary for a First Visit to the 'Windy City'.

If you're looking for inspiration for your next city trip in the United States, a 4-day visit to Chicago should be at the top of your list.

Aside from being the third-largest city in the United States, Chicago has much to offer: the metropolis on Lake Michigan boasts fantastic viewpoints, modern architecture, many culinary highlights, and well-curated museums, parks, or tours to learn more about the city. Incredible views of the city with its skyscrapers await you everywhere.

There is so much to do that we believe 3 to 4 days is the minimum time you should spend in this exciting city.

If you have 4 days in Chicago, we have put together the perfect Chicago travel guide for you. Check out our recommendations for accommodations, restaurants, and all the attractions you shouldn't miss during your city trip. We started our 4-week road trip from Chicago to New Orleans and were completely thrilled by the city and its people.

We hope you enjoy your stay in Chicago as much as we did. Let us know if you have any questions and leave a comment at the end of the article.

Here, I've summarized the most famous landmarks in Chicago, as well as the historically significant sites and activities in the city. I'll show you which attractions in Chicago are worth visiting and share what I enjoyed the most.

Best Travel Time: Year-round, summer (July-August can be very hot, but still popular months and vacations in the USA). Our tip: Spring (April to June) or fall (September to October). Travel Guide: Travel Know-How CityTrip Chicago (compact with everything you need to know) Getting there: Find flights Book accommodation: booking.com Hotel: citizenM Downtown (here you can find 3 more real hotel tips for Chicago) Activities & tickets reserve in advance: Chicago CityPASS, Chicago All-Inclusive Pass, Get Your Guide Culinary Tours: Chicago Food Tours

Before your city trip, you should first consider how many days you want to spend in Chicago. Next, we recommend thinking about whether you want to spend your time only in Chicago or also take a day trip. Option 3 is, like us, you are traveling on a road trip across the USA.

How you decide is up to you. Each of these options is valid. There is much to see, especially in Chicago where there is much to do. Therefore, I advise you to wake up early in the morning (thanks to jet lag, that's easy) and make the most out of your stay. We tend to pack our days full because we are curious and want to see as many attractions as possible.

We have each spent 4 days in Chicago twice and recommend that you plan at least 3-4 days for the city.

In general, there is no limit for Chicago. We could create an itinerary for a week without feeling bored. We suspect that you may, like us, not only stay in Chicago. Therefore, we compile this 4-day route based on how we structured our first visit.

Note: Be spontaneous and react to sudden downpours, and then head to the excellent museums.

Our personal recommendation is to plan at least 4 days for Chicago on a first trip. That's the minimum to be able to discover the most important highlights and a little bit of culture (and the nightlife, too).

There is always a lot going on in Chicago, so you should book tickets for the Skydeck and 360 Chicago early. You should also reserve your ticket for the Architecture Cruise before your trip, as these tours are the best and most popular in the city.

Be prepared that Cloud Gate is only relatively empty around sunrise. During the day, thousands of tourists crowd in front of the city's landmark, even in darkness, it's still quite busy here. Only during heavy rain have we seen it empty.

If you have 2-3 days in Chicago, you can experience the city's major attractions and book a tour. We weren't able to see everything during our trip. Make a list of places you absolutely want to visit.

We arrived on a direct flight with Lufthansa from Munich. There are also direct flights from Frankfurt. For flights, we always check Skyscanner for the best connections. We booked directly with Lufthansa, which was better because our original flights were canceled due to COVID.

We advise you not to come to Chicago with a rental car. The traffic is immense, parking is scarce and expensive. We started our 4-week road trip from Chicago to New Orleans and picked up our rental car only after our stay in Chicago. That was the best decision for us.

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

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

Alternatively, you can rent bikes to explore the city along the beaches, Lakeview Trail, and Riverwalk. You can either use the Lyft app or download the Divvy app for Chicago. The principle is similar to e-scooters: scan the code, unlock the bike, and set off. Return it at the next station and pay for the time you used it. Note: E-bikes are more expensive than regular bikes.

We enjoyed cycling along the Riverwalk by Lake Michigan. There are also e-scooters available everywhere.

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 long. The temperatures are just right, and a gentle breeze flows. The water temperature of Lake Michigan also rises to up to 21 degrees during this time - perfect for a refreshing dip.

However, it also gets quite crowded. Hotels are more expensive, and the lines at attractions are long.

Therefore, we visited Chicago for the first time in October. As the leaves slowly turned yellow and orange, you can experience beautiful colors in the city. When it comes to the weather, you can expect anything: from sun and pleasant 24 degrees to cool 10 degrees with pouring rain and the typical wind howling through the streets in the 'Windy City.' We experienced it all.

Here you can find my detailed hotel recommendations for Chicago with pictures

If you still want to find another hotel, we recommend the platform booking.com, where we always look for accommodations with information and many pictures.

LOOKING FOR A HOTEL? For searching for a good hotel, we recommend the Booking.com platform. We always book our accommodations on this platform or directly through American Express, as we receive additional discounts with the American Express Platinum Card (here see details, only worthwhile for frequent travelers).

Chicago is a city with a rich history. There is much to learn, both from the Prohibition era with the 'Mob' around Al Capone and in terms of architecture. That's why we recommend a 2-hour Chicago Architecture Foundation Center River Cruise (not the tour included in the Go City Pass) as the best way to explore the city on the Chicago River and learn more about the history surrounding the attractions and architecture.

Tip: With the Chicago CityPASS, you'll save money if you want to visit the included attractions.

If you have already read several of our travel reports, you will have noticed that we enjoy filling our days with sightseeing and activities from morning until night. In Chicago, we woke up one to two hours earlier than usual thanks to jet lag. It's worth it.

Here follows our suggestion for a 4-day trip in Chicago:

We land around 11:45 AM. By the time we arrive at the Freehand Hotel, another 2 1/2 hours will pass. It's a perfect autumn day, and to stay awake, we explore the city on foot. We see the Chicago River and the Riverwalk, walk through Millennium Park, and see Cloud Gate (The Bean) in its full glory. Since we have the Chicago CityPASS and also the Chicago All-Inclusive Pass for Chicago (each of us tests a pass), we can enter the aquarium for free, for which I had reserved a time slot in advance from Germany (it's necessary because it is popular).

In Millennium Park, there's also the concert shell Jay Pritzker Pavilion, where concerts, operas, and even sporting events regularly take place in the summer (we arrive on the day of the Chicago Marathon, so there was nothing to see here). The park also features the BP pedestrian bridge and a series of giant face-shaped sculptures. A stroll is worth it; we go through the park multiple times during our further days in Chicago.

Leaving Millennium Park and heading towards South Loop's Museum Campus and the shores of Lake Michigan, you can admire the Rococo splendor of Buckingham Fountain in Grant Park. Normally, the water is turned off from mid-October. We were lucky, and it was kept on initially due to the marathon and persistently good weather. Two days later, the show was over.

The Latona Fountain in the Gardens of the Palace of Versailles served as the architectural model. If Buckingham Fountain seems familiar to you... The well-known sitcom Al Bundy is set in a suburb of Chicago. The opening credits were filmed, among other places, at the Buckingham Memorial Fountain, which locals nicknamed the 'Married with Children' fountain (after the original title of the series).

The Shedd Aquarium is perfect for anyone curious about the mammals and fish that inhabit the oceans and freshwater lakes. It is one of the largest aquariums in the world and houses more than 32,000 animals from all over the globe. In various aquariums and rooms, you can experience many fish, amphibians, reptiles, invertebrates, birds, and mammals up close.

Since the aquarium is very popular, be sure to reserve your time slot in advance. We were here because admission is included for free in the sightseeing passes. However, we would not recommend visiting it to anyone; the fish are often overcrowded in tanks, and the sight of the cute belugas in their small round aquarium can bring tears to your eyes. It reinforces what we already know: aquariums do not serve animal welfare.

Due to the summery-autumn weather, we eat ice cream directly in front of the aquarium from the food truck at Rainbow Cone. It is - for our standards - very sweet, but just the right refreshment. We actually wanted to head next to the adjacent Field Museum after our visit to the aquarium, but we realize too late that it only opens until 5 PM. So keep an eye on the time, or do as we did: return to the museum in the rain.

Here's the truck finder to find out where a food truck is currently located.

Now the plan is to take a taxi boat from the aquarium to Navy Pier. But we also missed the last departure at 5 PM. Since the sun is shining and it's a pleasant 24 degrees, we rent a Divvy bike to ride along the picturesque route on the Lakefront Bike Trail, a beautifully designed bike path along the shores of Lake Michigan, to Navy Pier.

Note: You only need the Divvy or Lyft app. You rent the bikes via the app. Note that e-bikes cost about double the price of regular bikes.

The Lakefront Trails of Chicago include walking and biking paths. The paths run from Ardmore Avenue in the north to 71st Street in the south, providing an important access point to the lake for recreation. Here you can jog, bike, or simply take a walk.

At Navy Pier, there is always a lot going on, as the pier is one of the most popular attractions in Chicago. There are many shops, restaurants, and rides. For children, the nostalgic swings or the regular carousel are a highlight. For great views, be sure to ride the Ferris wheel. Navy Pier is also home to the Chicago Children's Museum, the Chicago Shakespeare Theater, and a botanical garden.

If you're not like us (later on) trying Deep-Dish Pizza at Giordano's, you can visit the branch at Navy Pier.

For beautiful views, you should visit the Ferris wheel at Navy Pier just before sunset. Admission is included in the Chicago All-Inclusive Pass.

As we want to toast our upcoming trip and need a break from sightseeing, we treat ourselves to a beer in a beer garden (Margaritaville) at Navy Pier. We are not very picky but they have draft beer, and inside-maybe also of interest to you-a display with jerseys and memorabilia from the city's sports stars like Michael Jordan, Dennis Rodman, and more.

Now we really feel the jet lag. Since it's Monday, and the restaurants we were recommended are closed, we want something quick: Where can you find better fast food burgers than at Shake Shack? Since a branch is on the way to Northbridge and thus our hotel, we treat ourselves to quick burgers and fries.

The first day in Chicago has been wonderful, the city excites us from the very first minute.

We begin day two in Chicago with a ride on the Chicago River and search for alternatives in the rain. Because after the boat tour, it gets dark and pours like crazy. But in Chicago, there's always a Plan B, as the museums are top-notch.

We are not usually breakfast people, but I am especially weak for New York Bagels. Google says Corey's is offering these right near the hotel. So we order coffee and bagels 'to go' and make our way to the Riverwalk to pick up our tickets for the boat ride.

We then sit on a bench, enjoying our bagels in pleasant temperatures and sunshine while we wait for departure.

For over 29 years, Chicago's First Lady Cruises have been offering this ride on the Chicago River in partnership with the Chicago Architecture Center (which is also worth a visit, but we unfortunately did not have time for it). It is truly a unique opportunity to experience Chicago from a river perspective! Cameras are hot, as the skyscrapers and their history, narrated by a guide on board with audio commentary, are definitely worth seeing and hearing.

The 1.5 hours fly by, and we are even more excited about this city. This tour is truly the best way to experience Chicago! You will explore all three branches of the Chicago River and learn all about the architectural details of various eras and their builders. We genuinely recommend the ride; just ensure you choose the right provider and not one of the many others.

To eat at a trendy vegan restaurant, we head north after the tour to Albany. Kale my Name won the Veggie Award 2022 for the best vegan restaurant in the United States and the 'Best of Chicago' award as 'best vegan' restaurant...

... and rightly so. We order Three Empanadas, Cauliflower Wings, Tequeños, the award-winning Lentil and Cheddar Broccoli Soup (ask for small cups so you can try more of the other options), Tacos, and the Rainbow Cake.

Conclusion: The bit longer drive (UBER/Lyft) north of Chicago was very worthwhile.

After the meal, it starts to rain. Therefore, we decide to make up the visit to the Field Museum. The Field Museum of Natural History has amazing exhibits, like Sue the Tyrannosaurus Rex, a complete fossil that is 67 million years old and was found in South Dakota. With around 85,000 square feet spread across five floors, it is one of the largest museums in the world and one of the most visited institutions in the USA.

Those who think natural history museums are boring are mistaken. The Field Museum ranks among the most popular natural history museums in the world.

The crime tour with Chicago Crime Tours is ideal for learning more about the Mafia's activities and crime stories about Chicago gangsters like Al Capone, The Untouchables, John Dillinger, the St. Valentine's Day Massacre, and Prohibition. We will be driven by bus to the most important places and historical landmarks, like the Biograph Theater, Holy Name Cathedral, Harry Caray's Italian Steakhouse, and a few other locations (thankfully, as it will be extremely rainy that evening).

During the bus ride, videos and original footage from TV at that time are shown. We can wholeheartedly recommend the tour to anyone interested in the past and the internationally renowned gangsters of the 'Windy City.'

We end the day at the hotel bar Broken Shaker. Enjoying an Old Fashion cocktail along with flatbread with truffles and chicken wings, we reflect on all we've experienced.

We kick off day 3 in Chicago with the Big Bus. The weather is still not great, so we first go for seated sightseeing with audio commentary. We then explore another neighborhood (West Loop) on a food tour and visit a whiskey and gin distillery before wrapping up the evening at a blues bar.

We try the hotel breakfast and plan the further day and onward journey; Chicago is just the beginning of our road trip from Chicago to New Orleans (view travel report here).

It's still cloudy, but the rain has stopped. So we hop on the Big Bus and ride the full route through the city. We listen to the audio commentary (Tip: Check if your bus driver is as cool as ours; we opted for no headphones and the German commentary, as we were greatly entertained by his live announcements).

The view from the upper deck of the tour buses is ideal for taking photos of the popular sights from a different perspective. The route starts at the Riverwalk, where we board at 10 AM (thanks to jet lag - no problem) and takes us through the center, past my favorite street art piece by Kobra, to the Skydeck and Willis Tower, Millennium Park, the Museum Campus, Navy Pier, Water Tower, and Magnificent Mile as well as 360 Chicago.

It's an ideal way to get an overview of Chicago - and especially recommended right at the beginning of your trip.

After the tour, we're hungry. So, we decide to find out what the Chicago-style hot dogs are all about. So far, we only know: one does not eat them with ketchup. We head to the popular Portillo's and are also impressed by the location. We order both a Maxwell Street Polish and the famous Chicago-style hot dog.

The latter is sour and spicy, an absolute delight; the sour pickles give it bite, juiciness, and a refreshing kick, while the hot, hearty sausage and the sweet-and-salty bun add to the heartiness. Wow!

The 'Polish' variety somewhat reminds us of bratwurst with fried onions. Not bad and not wrong - but the favorite is clearly the Chicago hot dog.

We walk along the Riverwalk into the West Loop neighborhood. The hipster neighborhood offers not only impressive street art but also a Time Out Market and many good restaurants, cafés, and bars. Therefore, we take the Gateway to the West Loop Food Tour with Chicago Food Tours. We don't want to reveal too much about the individual stops because we want you to explore the locations yourself.

Just one place we want to mention: Bonci Pizza. A delicious slice of pizza as you know it from Italy. Authentic and so good that Bonci even appeared on Netflix's Chef's Table Pizza (Episode 2 Gabriele Bonci).

We visit the KOVAL Distillery, the distillery that was the first to open after over 100 years after Prohibition to distill whiskey and gin. Founded by an Austrian immigrant in 2008, KOVAL has been on a successful course since. The gin and whiskey are not only shipped in the USA, but also to Japan and Europe.

We are shown everything on a tour and then, of course, sample the products. If it weren't for our excess baggage problem and a 3-week trip ahead of us, we would have definitely bought a bottle or two.

Next door, there's a cozy little bar where we mix cocktails according to our preferences with KOVAL gin and whiskey. Here you can see the regularly held events (like Book Swap).

The best and most authentically deep dish pizza in Chicago, according to locals, is at Pequod's. Unlike the competitors and big corporations, this place is still privately owned. In this small restaurant in northern Chicago, you'll only find locals.

Unfortunately, the wait for a table is about 1.5 to 2 hours. We ordered takeout through their website and went to the bar next door to wait. So, our tip: Be sure to reserve a table on the website in advance! The thick, flaky, mozzarella crust is incredibly delicious, and for that reason alone, you should try a deep dish at Pequod's (we chose the smallest one, which was sufficient for the test).

In the evening we visit the Blue Chicago Blues Bar to listen to Luke Pytel and the band, as well as the legend Shirley Johnson, and enjoy authentic Chicago blues. The place fills up quickly, and we are glad to have been present early. The 'cover' for the band costs $12 per person. A nice conclusion to our third evening in Chicago.

Our last day in Chicago arrives. The day we visit museums and the two famous observation decks in Chicago. But first, we start with breakfast to go to enjoy at the shiny bean.

The stylish café offers bagels as well as sandwiches. As bagel fans, we choose our favorite, along with a coffee - and the day can start; the sun is shining, off to Millennium Park! Here we enjoy our breakfast (photos of the 'Bean' and the park can be found above on Day 1) before heading to our first art museum. Since the weather is lovely, we walk the whole way.

We would only recommend the Museum of Contemporary Art Chicago to real art fans. The works in the museum showcase modern and contemporary art that probably not everyone - definitely not us - would understand. Since the exhibition space is quite small, $15 seems fairly steep; however, given the prices in Chicago in general, it's justified. Decide for yourself. Admission is also included in the Chicago All-Inclusive Pass, making it free.

The 'Magnificent Mile' - as the name translates - begins just after the DuSable Bridge at Wrigley's Building. The nearly 2 km long street, which is found in the northern part of the long Michigan Avenue, aptly carries the nickname for the city's most famous high-end shopping street, where shops line up one after another. From luxury brands to H & M, everything is available. Not for us - but maybe for you?

However, keep an eye out for the Water Tower. It is one of the oldest buildings in the city (1869).

Would you like to eat hot dogs again like we did? Dewil Dawg is very popular among locals and much smaller and cozier than the widely mentioned Chicago-style hot dog vendors. The hot dogs are excellent, but Portillo's was just a tad better. Still, we can highly recommend this place if you're hungry near the Magnificent Mile.

From 360 CHICAGO, you get the best view of Chicago's skyline and Lake Michigan.

The observation deck on the 94th floor offers a spectacular view of the city. One of the main attractions is the Tilt; a closed, movable glass and steel platform that slowly rotates outward, tilting visitors up to 30 degrees over Michigan Avenue. Another attraction is the CloudBar, where visitors can enjoy drinks and snacks while admiring the incredible view. We had tickets with a drink (Margarita). Surprisingly good, worth it!

There are also interactive touch screens with information about attractions, neighborhoods, and businesses throughout the city. 360 Chicago offers not just breathtaking views of the Windy City but also gives visitors a unique opportunity to experience one of America's largest cities from above!

Admission tickets cost $23 for adults (aged 12-64), $19 for seniors (65+), and $15 for children (3-11 years). A day pass that grants access to Skydeck Chicago and The Ledge is available.

Garrett's Popcorn in Chicago is a staple of the Windy City, so we knew we had to visit the popcorn shop with its variety of delicious flavors. We chose the mix of the two classics: cheddar cheese and caramel. A crazy combination, but sweet and salty create a wonderful liaison here.

Garrett's has been handcrafting popcorn for over 80 years, and each batch is still popped with real butter and made in small batches to ensure quality. Whether you're looking for a savory snack or something sweet, Garrett's Popcorn will satisfy your cravings!

After satisfying our popcorn hunger, we head to the Art Institute of Chicago, founded in 1879, one of the most significant art museums in the world. It houses an extensive collection of approximately 300,000 works of art from various eras and styles, including masterpieces by artists such as Monet, Renoir, Rembrandt, and Picasso.

The permanent collections are divided into seven departments: African art, American art, architecture and design, Asian art, modern and contemporary art, prints and drawings, and photography. Additionally, the museum offers an impressive selection of special exhibitions throughout the year.

We wish we had more time here. Do you only have time to visit one art museum? Then definitely this one.

The light show takes place every evening at 8:30 and 9 PM (check the times on the website). It is a projection onto the top 12 floors of the Merchandise Mart building downtown Chicago. The light show showcases works by some of the world's most renowned artists and professionals and has become a popular destination for both locals and visitors alike.

Many people gather by the Chicago River to watch the spectacle during this installation in the evening.

This experience is even better after dark: 'Pie in the Sky' is the name of the event. During this time, only a few people are served their pre-ordered deep-dish pizza at one of four balconies at their own table. Enjoy the incredible view while you dine.

After this experience and with full bellies, we let an UBER driver take us to the Adler Planetarium at the edge of Lake Michigan. The nighttime skyline from this vantage point is also a highlight of Chicago. Afterwards, we fall tired into our hotel bed.

Before leaving Chicago for the south, we participate in a street art tour in Bucktown (Wicked Park). Bucktown (Wicked Park) is home to some of the best street art in the city.

With its bright colors and bold images, it's easy to understand why this area attracts visitors from around the world. The tour takes us to various murals and graffiti. You will also gain insights into the stories behind these artworks as told by the artists themselves. Whether you're a fan of street art or just curious about what makes this part of the city special, taking the tour with Off Beat is worthwhile.

With one of the two city passes for Chicago, you can save money during your visit to attractions, tours, and other activities. The pass grants you access to some of the city's most popular attractions, such as the Art Institute of Chicago, Shedd Aquarium, 360 Chicago, Navy Pier, and many more. A city pass is definitely worth it if you plan to visit several attractions during your stay in Chicago.

I am already writing a review of both passes so you can quickly find out which one is right for you.

We tested the following sightseeing passes: Chicago CityPASS and Chicago All-Inclusive Pass.

Before my trip to Chicago, I purchased the following travel guide: MARCO POLO Travel Guide to Chicago and the Great Lakes. It was the most current guide on the market after COVID. The guide is compact and tells you the essential things you need to know for a visit of a few days. And it includes not only valuable tips for the city with all attractions and highlights but also exciting stories and tips for restaurants and other special places.

Those who do not shy away from the English language should also check out Fodor's Chicago. It was even more comprehensive and ideal for our visit.

There are so many excellent restaurants and cafes where you can dine wonderfully. Chicago is rightly dubbed the Food Capital of the US. We can highly recommend the following:

When you're in Chicago, you should explore the city on foot! Even if you confine yourself to a specific area, you'll likely walk thousands of steps without realizing it. Sneakers or comfortable shoes are ideal.

Those were our 4 days in Chicago.

Leave us a comment if you have questions! We are curious about your highlights in the metropolis on Lake Michigan and look forward to your feedback.

Disclaimer: A big thank you to Choose Chicago for supporting the trip and this wonderful journey - our opinion is, of course, our own.

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