Top 10 Places to Visit and Most Fun Things To Do in Chicago

By David Bolaños on Aug 09, 2021

From the shore of Lake Michigan to the Skydeck of the famous Willis Tower, there is so much to see in the crown jewel of Illinois, Chicago. If you are planning a weekend escape, it can get overwhelming to decide what things to do in Chicago first.

So, we have brought you a Chicago 2-day itinerary, following which you can visit and experience the famous Chicago tourist spots. If you are looking for a guide about the non touristy things to do in Chicago, we’ve got you covered as well.

In this guide, we'll take a look at:

  • 1. What Is Chicago Known for That Makes It Worth a Visit?
  • 2. Where to Stay in Chicago?
  • 3. 2 Days in Chicago - Day 1
  • 4. 2 Days in Chicago - Day 2
  • 5. Bonus Segment: What To Do in the Chicago, Illinois Area?
  • 6. Frequently Asked Questions

What Is Chicago Known for That Makes It Worth a Visit?

Getting nearly 55 million tourists a year, Chicago is the second most visited city in the US after New York. All these visitors come to Chicago because there are a ton of things to do for everyone of all ages. Not only are there plenty of must see tourist spots in Chicago, but the whole city is a sight to behold.
Perhaps what sets the Windy City apart is that it was rebuilt from scratch over the course of history. The infamous Great Chicago Fire reduced a major part of the city to ashes in 1871. When the city was reconstructed, it was done with careful planning and extreme attention to detail.

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A dominant aspect of the reconstruction period and what Chicago is known for today was the urban skyline. To date, the Chicago skyline has a mix of architectural designs and trends from the whole 20th century. The beauty of the city is further magnified by the Chicago River, which calmly winds through the heart of the town, opening up additional fun things to do in Chicago for adults and kids alike.

From downtown Chicago attractions to activities in Chicago as a whole, there’s a lot that you need to do to make your 2-day visit worth your while. Below are our Chicago sightseeing recommendations for the most iconic landmarks to include in your two-day itinerary.

Must-See Landmarks in Chicago

The Bean

Officially known as Cloud Gate, the Bean is one of the top things to see in Chicago. This public artwork sits in the Millenium Park and acts as an entrance to the park. But what makes it a must see in Chicago is its polished curved surface that reflects the surrounding skyline, green spaces and the visitors.

360 Chicago Observation Deck

Chicago’s skyline is repeatedly ranked as one of its top attractions. The 360 Chicago Observation Deck, formerly John Hancock Observatory, offers one of the best places to experience Chicago’s skyline. This must see, iconic attraction soars 1000ft over the Magnificent Mile and offers you expansive views of the Windy City, Lake Michigan, the Chicago River and three surrounding states- Michigan, Wisconsin and Indiana.

The Magnificent Mile

Just like other famous places in Chicago, the Mag Mile has a fascinating history stretching back to the 1920s. This 13-block section of Michigan Avenue is known for its dizzying array of massive shopping centers, iconic architecture, historical landmarks and restaurants. These tourist spots combine to give you an unforgettable sightseeing tour of Chicago.

Chicago Riverwalk

The Chicago Riverwalk is a 1.25-mile stretch along the banks of the Chicago River. This walk, which can take 1-2 hours, treats you to a host of exciting outdoor activities and things to see in downtown Chicago. Among other things, you can explore public art, sip wine in one of the riverfront bars, explore the Bridgehouse museum and even fish at the jetty.

Chicago Cultural Center

For culture lovers, the Chicago Cultural Center is one of the city’s places to visit. This 1897 landmark is located at Washington Street and offers both paid and free tourist attractions to see in downtown Chicago. Some of the things to do inside the Chicago Cultural Center include exploring the Washington Street Lobby and taking free guided architecture tours.

Where to Stay in Chicago?

There’s no shortage of places to stay in Chicago, whether you’re a first-time visitor or a regular. Essentially, what matters are your priorities and what tourist spots you want to hit during your visit to Chicago.

Gold Coast is often cited as the best place to stay in Chicago, thanks to its relatively quiet and relaxed vibe. This is an exclusive district right near the water and bordering popular tourist attractions in Chicago, including Lincoln Park and the Magnificent Mile. Essentially, having your hotel at Gold Coast makes it possible to access most of the top things to do in Chicago during the day before retreating to a quieter environment for a relaxed night’s sleep.

Suppose you want to experience the perfect balance of amenities, location, and services that Gold Coast offers – consider Selina Chicago Hotel. Situated near Magnificent Mile street, Oak Street Beach, just next to Millenium Park, the hotel is central to most of the big attractions and fun things to do in Chicago.

After a thrilling tour of Chicago attractions, Selina hotel has all you’d need for a refreshing vacay in the Windy City, from a special bar with cool booths to a second-floor cafe library that offers exuberant views of the city.

The hotel is connected to a restaurant in a seamless way with phone booths and a coworking space. You’ll find all the amenities like a common kitchen, cinema, and a fully functional gym. There even are halls and event spaces that you can rent. And if you want to save money on your Chicago sightseeing trips, you can rent scooters and bicycles from the hotel.

Selina’s Top 10 Most Fun Things To Do in Chicago

2 Days in Chicago – Day 1

360 Chicago and TILT

The best way to start exploring Chicago is by having a bird’s eye view of the whole city. You can do that at 360 Chicago, formerly known as the John Hancock Observatory. This public observatory is situated on the 94th floor of John Hancock Tower, 875 N, Michigan Avenue.

If you like to see the skyline sipping whiskey or eating a steak, you can go to The Signature Room at the 95th, a restaurant in the tower, or to The Signature Lounge at the 96th, a bar.

360 Chicago also has one of the most unique things to do in Chicago – the TILT. A fully enclosed moving platform that literally tilts you over Michigan Avenue from the 94th floor of the tower, it is the highest joyride in the city.

The Magnificent Mile

The next must see attraction in Chicago is just half a mile south of the 360 Observatory Deck. It is the portion of Michigan Avenue from Oak Street to the Chicago River. The poshest area of the city, the Magnificent Mile, is home to over 270 restaurants, 50+ hotels, high-end retail spaces and infinite Chicago attractions that draw over 22 million visitors annually.

Even if you are not in the mood to shop from the pricey outlets on the mile, you can witness the likes of the Chicago Water Tower, the Tribune Tower, and the Wrigley Building in this area.

Go on a Gangster Tour

The top things to do in Chicago rotate around its interesting architecture, vibrant art scenes and numerous cultural attractions. While Chicago is a peaceful city today, it was not like that always.

This city has been home to some of America’s most notorious mob bosses, most notably Al Capone. While they left behind a dark history of bloody gang wars, the streets they once walked on make some of the best places to visit in Chicago today.

If you want to know more about this part of the history of Chicago, you can go on a guided tour of the Chicago Loop, an area of the city that was the hub of mob activity in the 1920s and 1930s. You might not find this on your casual Chicago visitors’ guide.

Experience Local Food

Your list of the best places and fun things to do in Chicago won’t be complete without experiencing this city’s delicious food. Chicago has regularly been ranked among the best food cities in the US, often coming second after New York. Thus, you can be assured that the Chicago food scene is worth adding to your list of places to visit here.

Here are some recommendations on where to eat in Chicago. This is not the final verdict, and you can and should gather local intel too.


This is one of the most decorated restaurants in all of North America and has been on Elite Traveler’s Top 100 Restaurants list six times. You can go to the Salon that offers a 12-course meal or, better yet, experience the Kitchen Table for ultimate luxury dining.

Ever Restaurant

Offered by veteran chef Curtis Deffy and businessman Michael Muser, Ever Restaurant is another of the best dining places Chicago has to offer. This restaurant is open Tuesday to Saturday. Due to its popularity, the dining process can take up to two hours, but the delicious 10-course meal will make it worth your while.


The location of this restaurant might not be the very posh one, but the interior and the dining are nothing short of perfection. There is a single menu offering ten courses that will take you on a delicious world tour.

2 Days in Chicago – Day 2

Skydeck at Willis Tower

The perfect start of your second day could be visiting the Willis Tower – a place rightly hailed as a must see in Chicago. It’s worth getting up in the morning so that you can avoid crowds and lines while visiting this iconic spot.
The Willis Tower is the tallest building in the western hemisphere. It was the tallest in the world in 1974 when it was built and held that title until 1998. The Skydeck at the top of this building offers some of the most spectacular views of Chicago city.

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For those who are not afraid of heights, the extended ledges made of clear glass that protrude four feet from the Skydeck offer even better views of the city below.

The Willis Tower was formerly known as the Sears Tower. Knowing the old name of this iconic building can come in handy as most locals still use

Millennium Park

Millennium Park is next on the list of cool places to visit in Chicago. The first thing to do is to take a photo of the Chicago skyline in The Bean at the park. It is a large mirrored sculpture at the park entrance.

Note that this is one of the most popular places in Chicago. If you want to have the place to yourself, you’ll need to go there early in the morning.

The Millenium Park in Chicago is part of Grant Park, which hosts other top attractions, including the Jay Pritzker Pavilion, the Crown Fountain sculpture and Lurie Garden.

If you visit in the winter, there is a free ice skating rink in front of the park. Pack accordingly if you want to take advantage of that.

Art Institute of Chicago

Once you are done seeing Millenium Park, the next destination is just nearby. There are many museums in the city, but this one is near the park and has a larger number of attractions.

It is not only one of the largest but is also one of the oldest museums in the US. and of course one of the most notable museums in the world. Tickets sell out fast so try to book in advance.

So, that concludes two days in The Windy City. However, there are some more amazing places to visit near Chicago that must be made a part of this Chicago visitors guide 2-day itinerary.

Bonus Segment: What To Do in the Chicago, Illinois Area?

If you can spare a third day, there are some Chicago attractions that are not in the city but are worth every mile you’ll travel to visit them.

Oak Park

Frank Lloyd Wright – Wright, the founder of the Prairie School of Architecture, is regarded as the greatest American architect of all time. He was one of the people who worked on the resurrection of the Windy City after the great fire of 1871. He’s credited for some of the most iconic places to visit in Chicago, including the Robie House, Emil Bach House and The Rookery Building’s Light Court.

Oak Park, just 10 miles west of downtown, has the largest collection of examples of Wright’s work in the world. From public-access properties like the Unity Temple to private residences like the Bootleg Houses, these show how the Prairie School of Architecture evolved over the years.

Brookfield Zoo

If you’ve exhausted your desired places in Chicago and are in the mood to get acquainted with some polar bears, the Brookfield Zoo beckons. Look at bottlenose dolphins up close, see alligators in the wetlands, or witness the big cats. If you are already in Oak Park, the Brookfield Zoo is just three miles further west, a total of 13 miles from downtown Chicago.

Illinois Holocaust Museum

If you want to remember the past and pay tribute to the memories of the ones we lost to the atrocities of the Second World War, the Illinois Holocaust Museum & Education Center is the best place for that.

This place houses more than 500 artifacts, hosts regular exhibitions, and even has the option of virtual reality experiences. It also boasts one of the largest collections of contemporary artistic responses to the Holocaust.

Situated in Skokie, this museum is 17 miles from downtown.

Ravinia Festival

If you visit Chicago in the summer (which is the best time for it), spare a night for the Ravinia Festival, a concert park 25 miles north of downtown Chicago. This park has seen everyone from John Legend to Aretha Franklin perform for the crowd.

This amazing amphitheater is the summer home to the world-famous Chicago Symphony Orchestra, a carousel, different restaurants, a sculpture park, and many more. Pack your bags and spend a night under the stars in this park to feel what Illinois is about.

Morton Arboretum

If you want an escape to nature, this is the best option you have. Situated 25 miles from downtown, this 1,700-acre public garden has some of the best things to do in Chicago if you are a nature lover. From walking in the oak garden to getting lost in the one-acre garden maze, this place has a lot to offer.

LEGOLAND Discovery Center

If you are in Chicago with your family, this is the best place to visit. From reaching out to touch stars in the 4-D cinema to riding a dragon in the Medieval LEGO Castle, there are a lot of activities in this joyland that amuse adults and children alike. This family attraction is also not very far away, just 25 miles from downtown.

Summing up the Best Things To Do in Chicago

Chicago is packed with fun things to do and exciting places to visit as a family, couple or solo. On a two-day escape, your Chicago itinerary could include major attractions, such as the 360 Chicago Observatory Tower, the Millenium Park and the Chicago Art Institute Museum. If you’re down for something a bit eerie in Chicago, complement your sightseeing tour with a gangster tour of the city.

After exhausting all of the fun things to do in Chicago, there are many more attractions just outside of the city, too, including Oak Park, Brookfield Zoo, Illinois Holocaust Museum, Ravinia Festival, Morton Arboretum, and LEGOLAND Discovery center, to name a few. In short, your trip would be worth every second!

Top 10 Things to Do in Chicago FAQs

  • What is Chicago the most famous for?

    Situated in the state of Illinois, Chicago is one of the most famous cities in the US. It is known for its bold architecture, shopping experiences, unique food scene and one-of-a-kind architecture. The best places to visit in Chicago include the Millenium Park, 360 Chicago Observation Deck, Navy Pier, Magnificent Mile and Chicago Riverwalk.

  • What is the most famous street in Chicago?

    The most famous street in Chicago is Michigan Avenue. This is a north-south street that is situated at 100 East on the Chicago Grid. The northern end of the street touches Lake Shore Drive on the shore of the famous lake Michigan. It is 20 kilometers long and connects the Gold Coast historic district with Motor Row District. One of the top places to go in Chicago for most natives and visitors, Michigan Avenue is home to several must-see landmarks, including the Millenium Park, Chicago Water Tower and the Art Institute of Chicago.

  • How many days do I need to explore Chicago?

    The places to visit and things to do in Chicago are enough to keep you around for up to a week, depending on your travel style. But you can cover most of the things to do in downtown Chicago in 2-3 days.

  • What should I do on my first day in Chicago?

    The best things to do on your first day in Chicago include:

    • Observing the city from 360 Chicago.
    • Riding the TILT.
    • Enjoy the delicious street food that the city has to offer.
    • Have fun at the Millenium Park.

    Other tourist attractions not to be missed in Chicago include shopping at the Magnificent Mile and going on a gangster tour through the Loop.

  • How long does it take to see the Willis Tower?

    One hour is sufficient to observe the beauty of Chicago from the Skydeck of Willis Tower. However, depending on the time of the day and the time of the year, you might need to wait in line for up to two hours. As the tallest observation deck in the USA, it’s not a mistake that the Willis Tower is one of the most famous places in Chicago. So, go early if you want to beat the lines.

  • Where is the tilt in Chicago?

    The Tilt is among the newest things to do in Chicago. It is a joyride situated at the top of the John Hancock Observation Deck. It can hold up to eight visitors and extends outside the skyscraper into the air to provide a 360-degree view of the city.

  • What should I pack for Chicago?

    What you need to pack for a tour to Chicago depends on the season and the places you plan to visit in Chicago. The most important thing is to pack appropriate clothing, especially in the winter as it gets very cold up there. Other than that, pack comfortable walking shoes and a refillable water bottle.

  • Is Chicago expensive for tourists?

    That depends on what you plan to do in the city, where you stay, and which places you visit. Chicago downtown has the same prices for food, accommodation, and transport as NYC or DC. As you’d expect, visiting the famous tourist attractions in Chicago will cost you quite some money. But that’s not to say that you won’t find cheap and even free yet fun things to do in Chicago.

  • What is there to see in Chicago for free?

    There are tons of free places to visit and things to do in downtown Chicago. Here are our top 10 recommendations of free Chicago attractions:

    • Chicago Cultural Center 
    • Lincoln Park zoo 
    • Smart Museum of Art 
    • Grant Park 
    • Space exploration at Adler Planetarium 
    • Garfield Park Conservatory
    • Millennium Park 
    • Lakefront trail 
    • Chicago Riverwalk
    • City Gallery at the Historic Water Tower
  • Selina Chicago

    Benefit from beautiful accommodation, daily wellness, high-speed internet, and more at Selina Chicago

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