18 Top Things To See And Do In Chicago

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Globalisation made travel from one continent to the other so amazingly easy. Communication and cultural exchange are more and more desired by all of us. We, as a human being, are known for the curiosity we show, wanting to see, learn and explore other places.

Going long distances for our holidays, or even weekend breaks are more and more on our to-do list.

Chicago is one of the cities we see very often pictured in the movies, and that it’s because of Chicago it’s one of the top favourites cities when it comes to where to shoot a movie.

Due to its incredible layout of the place, the huge size of the green spaces, as well as the beautiful beach on the shore of Lake Michigan, but especially because of the beauty of the Conservatories spread around and  the attraction of the oldest Zoo in USA makes it just the perfect spot for any kind of stories.

I am sure that many of us, watching any of the movies filmed there, find ourselves wishing we go and see the places at least once in a lifetime.

Today is easier as ever. You can find a really cheap flight to help you make your dream come true.

So why don’t you take the leap and book an amazing visit there? Whether is during the holidays, when Chicago is one of the best holiday decorated city in the world or any other time – you will find plenty of attractions to see or activities to participate in.

The city is filled with amazing sightseeing venues, bold architecture, towering skyscrapers, vast green spaces and numerous museums. Chicago Art museums are very appealing, especially among art lovers.

Visit Chicago

What can we say about this glorious city? Not enough.

House to The Every Girl headquarters, among the very best food and cultural destinations in the U.S., along with a place that has something for everyone, this city has really captured our hearts.

 When is the best time to visit Chicago

Any time. This amazing place has a lot to offer in every season. Chicago in spring is amazing as you can see the nature turning from the bitter cold of winter and the grey earthy looking fields to the beautiful blossoming environment. Summer in Chicago is an amazing time to visit due to its longer days and its hot weather; however, the weather in the summer tends to get really hot so tread carefully when planning. Autumn in Chicago is one of my favourites time to visit the place as the weather starts to cool, the days are still fairly long and the colour of nature is just amazing. Chicago in winter can be very cold and very windy, so make sure to check the temperatures, especially if you are not fond of cold.

Is Chicago worth visiting? 

Yes, definitely. There are so many unique places to visit in Chicago, from a tourist point of view sightseeing important places in Chicago but also there are lots of non-tourist things to do in Chicago, such as enjoying and relaxing in the many green spaces, visiting museums in Chicago and enjoying lovely evenings in dining places with live music.

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You might also wonder if: is Chicago safe?

Then I think the best answer is that Chicago is like any of the other large and busy cities. There are places that are not advised to adventure alone or/and at a late hour and in general to be sensible about your whereabouts.

Where To Stay?

First on the list is the above question: where to stay?

Create your time special if you are visiting the thrilling city of Chicago and choose to stay in among the best places.

There are lots of quality accommodation guaranteed to ticks all your boxes, so do your homework and choose from the great variety based on your wants and needs.

A lot of the hotels in Chicago have top class amenities, like the spa and a few boast dining restaurants that are excellent also.

Although the city is filled throughout with great places to stay, suitable for different budgets and various types of events, we want to point out the only couple of them that are quite hot to be in right now.

Located in one of the hippest along with most well-known neighbourhoods in town, but tucked away from the hustle along with the bustle of the Loop, The Publishing House B&B is in a perfect location for anyone who would like to visit the sights and hit the city, but also unwind.

Freehand Chicago River North – The Freehand, although not exclusive to Chicago, is an alternative for groups rents two or a bed or it is possible to opt to stay rooms.

Friend groups can select rooms with four beds and a seating area making this a spending budget choice for women trips or bachelorette weekends. House to among the best rooftop bars in town and right on the street from Lincoln Park and its famous zoo, it is a great place for anyone who would like to remain off the beaten path of town, but still wishes to live it up a bit.

Not only can there be an event space and bar, a Shake Shack on the floor and the rooftop bar on the top, but it is also a perfect location for everything outside the building.

Take note! – Hotel Zachary Wrigleyville – If you are in town for a Cubs game, the new Hotel Zachary cannot be beat. Not only is it LITERALLY across the street from Wrigley Field, but is close to Wrigleyville’s super fun row of rowdy sports bars along with tasty late-night eats.

Ace Hotel Chicago West Loop – The Ace Hotel is a super fun boutique hotel situated just a stone throw away from some of the biggest headquarters in the city. Not only is it a great place to stay, but it is also a great place to visit. They have a tasty downstairs restaurant/bar/coffee shop with outdoor fire pits and a fun indoor/outdoor rooftop bar with drinks special items along with an even better view of the town.

Thompson Chicago Gold Coast – This stylish loft-style Gold Coast boutique hotel is one-of-a-kind to offer you downtown vibes with the comfort of an at-home feel. Delicious food, great atmosphere, ideal location, and a cost that won’t break the credit rating!

Soho House West Loop – In contrary to common belief, you do not have to be a Soho House member to remain in the Chicago outpost of the luxury chain. So check it out before your visit.

No matter where you choose to stay, any destination is easily accessible as the Chicago public transport network is one of the best in the world.

A Short Introduction To Chicago

Escape, once you’ve settled into your accommodation, and explore this fantastic city. On the doorstep, the highlights of the city are from any among the hotels in Chicago.

The Windy City, which is Chicago’s famous nickname for its political arena offers something distinctive.

Chicago is located on Lake Michigan in the state of Illinois and is one of the largest cities in the USA.

Famous for its Blues legends, its music scene and its rhythm, the city has some great music places to go to get a first-class night out.

For action throughout the day, you might like to visit Wrigleyville for a Cubs ball game that is thrilling. Packed with cheer, enthusiasm and a good deal of fun this is an adventure not to be missed. This park is the oldest in the customs, as well as the major leagues and legends, ooze from each corner.

Although the Chicago Cubs team tends to be more popular among the baseball fans, the Chicago White Sox baseball team is the oldest and is admired by a great number of people. I, myself, proud to say that it was the White Sox team I choose to watch while visiting Chicago.

So, if you have no preference, then White Sox Stadium – Guaranteed Rate Field in South of Chicago is a better option (especially if you are travelling with kids) as it is cheaper and has a great parking space as opposed to the Wrigley field, which is home to Chicago Cubs. Also, the south stadium has more room to roam, better food choices and good seats. And lastly but not least, we must mention the great entertainment that offers exciting fireworks.

If the game is not your thing, a trip to the free zoo of the city must be on the schedule. Bordered by the vast Lake Michigan, Lincoln Park Zoological Garden is the oldest zoological park in America. A spectacular place to explore and this attraction is one activity suitable and full of fun for all the family.

The city has no shortage of museums as well as boasts among the world’s most famous galleries. This architectural jewel unfolds into marble and glass walkways and tens of thousands of rooms full of paintings, drawings, sculpture and photographs. That is a definite must to get to see for the art lovers.

During a long day sightseeing, you will have to make certain food and snack stops to keep the levels of energy up and that is a perfect excuse to taste the world-famous Chicago pizza pie. These tasty pies, cooked in a frying pan without a handle, and ending up in the oven so that the encased mozzarella, tomato and meat could be oven baked are just heavenly tasting.

If you are searching for a more calming sightseeing experience, why not take just a trip on the river? This is a lot more refined way to find and see the city, enjoying the architecture and avoiding the mad chaos at the same time.

The city skyline is famous through the United States and there is nothing quite like experiencing it from the luxury of a river tour. A lot of the best resorts in Chicago will offer to assist you to pre-book these tours as well as even take you to the boats if you need too.

Another top attraction of the town is the beach. In the summertime, the miles of golden sands on the coasts of the Lake Michigan are filled up with volleyball players, joggers, sunbathers as well as swimmers. But, most of all it can make a great day out for all those wanting a little sunshine and relaxation. Also, North Beach is a perfect stopping point after visiting Lincoln Park and its attractions. From here you can take a nice long walk on the shores of the Lake back to the Loop and the Downtown attractions.

Lastly, but not least, let’s not forget about the green spaces, as Chicago is quite famous for it, being proud of the name of the city in a garden.

Top Attractions In Chicago

Chicago is a wonderful city to visit. Whether you are passing through and just have a couple of hours, or you are choosing it as a city break destination or even better as a holiday place you will definitely be amazed by the vibrant and in the same time relaxed atmosphere of the city.

As mentioned earlier, the Windy City has something distinctive to offer each of us, whether you are an art lover, a nature enthusiast or just looking for some fun and great entertainment for your holiday.

However, no matter the reason for visiting the city, there are a couple of places you should make sure you see before leaving, as they are landmarks of the place and they are the following:

Michigan Avenue and the Magnificent Mile. Michigan Avenue is a very attractive boulevard, offering many luxury shops, boutiques and galleries. The Avenue is home to some of the most outstanding skyscrapers such as the Tribune Tower, a neo-gothic structure, the Wrigley Building and the John Hancock Center.

John Hancock Center is one of the cities of skyscrapers. On the 94th floor, it has the 360 Chicago observation deck, from where you can admire the views of the city’s skyline and Lake Michigan.


Willis Tower (formerly known as Sears Tower) was until 1996 the tallest office tower in the world. The tower is 1453 feet tall and has an observatory named Sky Deck on the 103rd floor from where you can have an amazing panoramic view of the entire city. It has been said that from this observatory you can be able to see on a clear day four different stated. Extending out of the Sky Deck there is the Ledge, which is a glass box, with a glass floor where you can enter and see the city around you and below you.

Navy Pier is a great place to spend with the entire family as it covers up to 50 acres of gardens and parks, shops and concert venues. You have here, a museum for children, theatre, various dining options, a 150 foot Ferris wheel and amazing street architecture

Millennium Park is part of the Grant Park, and is home to the Cloud Gate – the bean-shaped art, that offers distorted  reflections, is very popular for selfies and its truly the best icon of the city; if you are visiting the park over the summer then you can enjoy lovely strolls around it and through the serene Lurie Gardens; and try to catch a free concert in the Frank Gehry-designed Jay Pritzker Pavilion; however, if you are visiting in the winter you have a great opportunity to skate on the McCormick Tribune Ice Rink. Also, be sure not to miss the Crown Fountain – on a hot summer day you will have an amazing splash there.

Buckingham Fountain, located in Grant Park, is one of the largest fountains in the world and it is designed in the Art Deco style. It is one of the best city’s landmark so be sure not to miss it.

The Green Mill is a historic jazz club and is the place where Al Capone and his friends used to hang out. It is a cocktail lounge filled with live jazz so try and visit it even if only for a couple of minutes.

Wrigley Field, home to Chicago Cubs team, is a great place to see for the baseball lovers.

Garfield Park Conservatory is one of the largest greenhouses in the USA, hosting over 600 species of plants, most of which are not even native to the region. Free admission.

The Peggy Notebaert Nature Museum is an oasis of peace and relaxation, with interactive displays on river and marsh eco-system as well as a Butterfly Haven.

Lincoln Park’s flower-filled gardens and Conservatory. Free admission.

Lincoln Park Zoo, located in Lincoln Park, is one of the oldest in the USA, hosting more than 1000 animals. This is a lovely place to spend even a whole day on good weather as there are lots of green places to walk around. Free admission.

Museum of Contemporary Art displays one of the largest collections of modern art in the USA.

Art Institute of Chicago hosting a great number of Impressionist and post-Impressionist works

Museum Campus, right on the shore of Michigan Lake, hosts a number of few museums that are great to visit.

Shedd Aquarium, home to aquatic creatures from around the world, will make up for an amazing and unforgettable experience.

The Field Museum displays the greatest collection of natural history in Chicago.

The Adler Planetarium hosts a great number of events and exhibition.

Museum of Science and Industry, located at the north end of Jackson Park, offers a huge display of a model railroad illustrating the 2200 mile journey from Seattle to Chicago. Also, you can walk around a re-creation of a Chicago street from around 1910.

Chicago River Architecture Tour. Choose this option if you are in a hurry but you want a good taste of the bold architecture the city has to offer, along with a good narrated history of each outstanding building. 

Chicago Riverwalk: take a stroll along the main branch of Chicago River to admire the outstanding architecture along with witnessing the locals and other tourists passing by. 

As mentioned above, a boat tour trip is a great way to explore Chicago but also want to point out that the Hop on hop off trolley tour is the easiest way to visit this gorgeous city on a short time. However, if you are lucky enough to have more days to explore than a walking adventure is the best as you can totally grasp not only the outstanding architecture and the breathtaking views but also the vibrant culture of the city. Therefore, I totally recommend planning carefully in advance and deciding what it is that you are aiming for.

Ending Note

No matter the distance you are travelling from, Chicago will make your visit worthwhile. It is indeed one of the best places in the world to spend at least a couple of days. It offers a great variety of options to please each taste. From the art and history lovers to the culture hunters, and from food and entertainment enthusiastic to nature passionate, the Windy City has it all.

Do not hesitate to book your holiday there – you will not be disappointed. I am sure that you will want to plan a return to Chicago as soon as possible, as it is the city that makes you feel like home.

Hope that the article really helped you to picture the uniqueness of the city of Chicago and that will help you when planning your trip.

❗Please, if you like what you have read, share the article so other people can benefit from it❗

Until next time,

Oana and Paula

One Reply to “18 Top Things To See And Do In Chicago”

  1. Hello,

    The USA is one of the best countries to be visited. My uncle lives there for more than 20 years now and he always talks about how awesome this country is! I always wanted to visit cities such as New York, Washington DC and Chicago.

    It is amazing to know that Chicago has so many places and things to visit and see. I am planning to visit my Uncle next summer and I will definitely visit Chicago. I want to visit Michigan Avenue, Millennium Park and the Shedd Aquarium.

    I loved reading this article and I can say I started to love Chicago even before visiting it! I bet as you said Chicago will be worthwhile visiting it!

    Thank you for this amazing post!

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