12 Best Things To Do in Chicago For First-Time Visitors [Bucket List]

Visiting somewhere new can be a lot to take in. But if you have time, there is so much to take in that it staggers the mind and becomes clear no one day at Comic-Con can capture everything.

Dazzling Chicago is a city in the Midwest, and I had drawn up a long list of things to do before my visit. So, it is no doubt that my excitement had me creating a list of enough things to do for all the 2 months.

This was all the more reason to make sure that my local friend from the city ensured I had a memorable experience for myself.

To help you plan your travel, I have written this list of things todo in Chicago for a first-time traveler and even long time visitors like my friend and me.

Top Things To Do in Chicago

1. Discover Chicago from Above with a Bird’s Eye View

My absolute favorite way to see a new city is in the sky. Whether it’s scaling a historic church in Amsterdam or climbing a fortress to the top of Kotor, Montenegro. In Chicago, it translates into a quick trip up an elevator to the 94th floor of the John Hancock Center.

The view from the 360 Chicago observation deck is a stunning panorama of the city. This lovely lady has a bar on board where you can take in your surroundings while sipping a tipple. The TILT experience is also on offer for those who seek a thrill. This glass and steel structure juts out of the building, giving you a one-of-a-kind view of the Magnificent mile from 1000 feet above.

It costs about $30 to go up on the observation deck for adults. There is an extra charge for the TILT experience, but you can skip it if you want to save a little money. You must purchase your ticket before visiting to avoid a big queue.

2. Shop On Magnificent Mile

Up there on the list of things to do in Chicago is this opportunity for a leisurely walk round its best-known shopping district. And then there comes the Magnificent Mile of Michigan Avenue, an overabundance of affluent shops, wardrobe enclaves, luxurious meals and some beautiful inns.

This street is also lined with distinct landmarks such as the Chicago Water Tower, Wrigley Building and the towering John Hancock Center. The Escape Game is one way to provide entertainment within the mall area along with shopping.

In fact, the Magnificent Mile is actually one of America’s most expensive neighborhoods—behind only New York City’s Fifth Avenue and Beverly Hills’ Rodeo Drive.

If you roam the Magnificent Mile and some other parts of downtown you will see a number of Dolly designs in which German Shepherd sculptures are painted. These are artworks devoted to the memories of police officers who have died or been injured in the line of duty. Be on the lookout for these laden sculptures as you traverse.

3. Chill at The LondonHouse Rooftop Bar

Just imagine sipping on a cocktail high above the city and watching boats cruise down the Chicago River. If this catches your fancy, you must check out the roof top bar at one of their best hotels.

A four-star experience in a historic building from the 1920s just across from the famous Riverwalk, LondonHouse Chicago Sip on drinks while being treated to amazing perspectives of the Chicago River, Magnificent Mile and even Lake Michigan, from the 3 stages of rooftop bars at this hotel.

4. Unwind in Millennium Park

Millennium Park is a favorite free activity, so you’re not considered an actual first-timer in the Windy City until you’ve strolled through it at least once. Home to the iconic sculpture, ‘Cloud Gate’ which is better known as ‘the Bean’ was built in…

Millennium Park hosts more than just this fanciful sculpture, it is also an urban oasis in the heart of downtown Chicago. You can also enjoy the beautifully landscaped Lurie Garden and its inviting green space – perfect for a peaceful retreat.

The park is also home to the Boeing Galleries where you can take in some outdoor art and Jay Pritzker Pavilion that stages free music festivals. With or without a festival, the pavilion area makes for a perfect location to lay out blankets and enjoy a picnic while you watch the sunset.

A friend told me that at Christmas it turned into this magical place with an ice rink and things just to bring a light to the whole area.

5. Wander the Chicago Riverwalk

Chicago is also home to lush green spaces like the aforementioned Millennium Park and Gardens that are ideal for a summer walk. The popular Chicago Riverwalk is a perfect spot to take in the views of the city’s snaking river.

Though its a walking path next to the waterway at first, Riverwalk is more than what might show. There are some lively outdoor bars and riverside restaurants to grab a drink or bite at. Also in the area are a museum dedicated to the Chicago River and more than 20 pieces of outdoor art placed throughout along the path.

For a more exciting option, hop on one of Chicago’s kayak tours or experience the city skyline from an engaging boat tour. Both day and night on the Riverwalk provides a sense of space not elsewhere to be found in Chicago. I visited it alot when I stayed in the city and great affection for this place. And DEFINITELY one of the top things to do in Chicago!

6. Discover the Trendy West Loop

If you truly desire character, then look no further than West Loop. What was once an industrial district is now Chicago’s Episode East, crowded with the Urban cool who brace one of America’s most magnetic dining and nightlife scenes.

The former warehouses have been transformed into some of the greatest restaurants in The Windy City, especially around Fulton Market where trendy industrial vibes are king.

There will be dozens of restaurants and cafes to choose from in the area. One such place is a nice hideout, Sawada Coffee located in graffiti-splashed building. WH Grist & Sons A stylish coffee bar that gets it right on the caffeine front. But even if you’re not a coffee drinker, there is something else here that completely sets itself apart from The Sea; the most unique expression of the “Military Latte,” which is like a Matcha Latte on another level.

7. Have a Night Out at Noyane Rooftop Bar

Though it may not be easy to beat the views from LondonHouse’s rooftop bar, another incredible spot that shouldn’t be missed is the Conrad Chicago’s Noyane. It may not have the all-encompassing view of its new sister, but it’s certainly just as cosy — if not more so.

The ambiance includes modern furniture, a cozy fire pit, plus a roomy bar that serves an array of drinks. Hungry and dont want to leave the But if youve worked up an appetite, tuck into one of top-of-the-roof Japanese-Peruvian restaurant offerings.

8. Ride the Ferris Wheel at Navy Pier

Afterwards, we made our way to Lake Michigan and Navy Pier (a 3,300 foot-long pier on the Chicago shoreline).

Perfect for a day of outdoor fun with lots to do in the great outdoors! There is a sensory maze, botanical garden, musical carousel, and Chicago Children Museum to boot.

The most well-known attraction to the pier is certainly the 60-metre-high Chicago Ferris Wheel. It gives some of the amazing views into the city skyline while rotating on its gentle axis.

Children ride ticket$12 each Adult ride ticket$20 each Certainly this is not the most cost effective thing you can do, but it was definitely worth every penny with outstanding views across to the lake from above. Getting there: to skip the line buying tickets for your visit from home.

9. Wander Around the Old Town & Pop Into Its Cutest Little Cafe

As we talked about West Loop you know that Chicago is not all about the tall high rises. Numerous neighborhoods outside of Downtown are just as inviting, such as charming Old Town. The suburb, which has a population of around 10,000 is famous for its federation era houses that resembled an old English town with plenty of leafy streets lines with boutique shops selling goods not available in your average Westfield, traditional pubs and artisan coffee houses.

One of the most notable ones is the 3 Arts Club Café has its home nested within Restoration Hardware store. The very first time I entered it almost took my breath away; I had never seen a café so stylish in my life. Complete with crystal chandeliers hung from a glass ceiling, extravagant centre fountain and greenery draping every nook and cranny, it would be easy to mistake the place as a wedding venue.

And you’d think that the prices would equal luxurious decor, but it was refreshingly affordable. Honestly, drinking a coffee or Chai Latta — my personal favorite while sitting under those magnificent chandeliers, ranks at the top of things to do in Chicago!

10. Skydeck Chicago at the Willis Tower

The following experience is definitely not for the weak in a high place. Rising amid the towering Chicago skyline, where it rubs shoulders with the likes of the John Hancock and Trump towers, Willis Tower reigns as tallest.

Originally built in 1973, this was a taller skyscraper than any other in the world for almost thirty years.

Your adventure starts with a rapid elevator (60 seconds) on the 103rd floor, you might notice that sensation of changing whether many find it some unsettling.

On the top there’s the famous Skydeck, one of the highlights for most tourists in Chicago. Although the panoramic views are stunning, they were built with glass balconies in 2009 for some added excitement. Each balcony sticks out over a meter from the building, so you can look down at the bustling city streets and feel as if it were strange to be right beneath your feet.

Be sure to take some pictures; the Skydeck is one of Chicago’s top Instagram spots.

The Skydeck has tickets from $36, and advance online purchase is recommended to avoid long lines.

11. Chinatown Eats – One Bite at a Time

In many large cities throughout the United States, such as New York City, Los Angeles San Francisco and, of course, Chicago, Chinatown is a destination not to forget. A 3rd and ultimate neighborhood others the coolest things to do in Chicago.

Of any region in the city, this one is most lively and making it playful. There, you can treat your tastebuds to tour of regional eating establishments, hidden gems and dimatters sum diners or unwind over a steaming cup of tea in one the many authentic teahouses.

Once your food needs are met, delve deeper into the cultural tapestry of this lively community. The American Museum of Chicago is a great place to get the texture of Chinese immigrant life, but I was able to suggest better areas if you are looking for somewhere more meaningful.

12. Take in the Skyline from North Avenue Beach

My favorite spot in Chicago – lastly, the beach at North Avenue Beach, when you are there a must visit. Beloved public beach in Lincoln Park bekannten zu schwimmen, aber sie versteht es auch: Die am meisten von Brooklyn getrennte Saison (Strauß bostigt).

The lakeshore is a buzz with activity year-round — whether rollerbladers, bikers or walkers on the path. The panoramic view sky line of this beach left deep impression in me and I not able to forget it even after my 1st visit, it made me visit this place twice.

We watched the sun set on one of our visits, and as night took hold the lights of the skyline seemed to flicker across its waters with many facets. I was snapped back to reality by the passing of a runner who stopped just up ahead with his friend, awestruck at the sight. I responded with nothing more than that same agreement; all but speechless, awe-filled by my departure from the city.

That night is one of the most unforgettable nights in my life, and I could not have asked for a better end to an amazing week in Chicago. I hope you love this city as much as I do!

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