Experience Chicago with These Top 9 Places and Spaces


Accommodation/ Lodging   Arts and Culture   Explore Chicago  


The Windy City is a unique place where history, art, culture, and modern flair collide in the best of possible ways. Travelers have been enjoying the city’s vibrant colors, flavors, and people for many years now, yet there’s always something new around every corner.

I highly recommend any traveler add Chicago to their travel plans and experience this one-of-a-kind city for themselves. Read on to see my personal list of top places and spaces not to miss while you’re there, including where to stay, what to see, and what to do!


Staypineapple Chicago

Staypineapple Chicago Picture Credits: Staypineapple Chicago


In a city chock full of awesome—cuisine, art, architecture, shopping—you’ll want your hotel to measure up. Staypineapple Chicago does not disappoint. An Iconic Hotel just steps from Millennium Park, Staypineapple Chicago is housed in a National Historic Landmark building and is the perfect jumping off spot for exploring downtown Chicago.

In the Loop and with the Theater District just steps away, you are poised to take full advantage of all the city has to offer. Take in the collections of the Art Institute of Chicago, shop the glam shops and boutiques of the Magnificent Mile, marvel at the details of the Rookery, or cheer along with the crowd at one of the city’s many festivals, all before returning to posh accommodations and deluxe amenities.

If you’re looking for something with incomparable style, grace, and warmth, Stayinpinapple Chicago is for you.


360 Chicago

360 Chicago Picture Credits: 360 Chicago


Offering panoramic views of the city from all angles, there’s no better way to see the real Chicago than at 360 Chicago. The 360 Chicago observation deck, located 1000 feet above the famed Magnificent Mile in the iconic John Hancock Building, offers breathtaking 360-degree views of Chicago’s skyline and Lake Michigan. 360 Chicago observation deck is also home of TILT – Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.

With its many interactive learning opportunities on the city’s rich history, colorful neighborhoods and its iconic architecture, along with a modern Bar and Café where you can relax and enjoy the best views of the city, 360 Chicago is the perfect place to enjoy an unforgettable experience while on your trip to Chicago.



CSz Theater Chicago

CSz Theater Chicago Picture Credits: CSz Theater Chicago


CSZ Theater (the home of ComedySportz) is the longest running short-form improv theater in Chicago and has been running for over 32 years! This interactive show is a comedy performed as a sport – and believe us, it can get competitive. Two teams, the Downtown Chicago Bosses in blue and the “Visiting Team” in red, compete in a battle of wits for the love, laughter, and applause of the audience, while a referee, host of the show, guides the action. If you love improv, CSZ is the show for you.

Everything is completely made up on the spot using audience suggestions and willing volunteers. Professional players make up games, scenes, skits, and more, all of which are completely unique and never before seen. This family-friendly show (designed to be appropriate for all ages, from age 8 to 80) is something truly unique. You can be sure that there’s nothing else like CSZ Theater in Chicago.



The Annoyance Theatre

The Annoyance Theatre Picture Credits: The Annoyance Theatre


A pillar of the Chicago improv and comedy community, The Annoyance Theater has been serving up laughs and theatrical art to audiences for many years, and has even offered improv classes since 1989! This place is a must-see for lovers of all things silly. And since they offer a full calendar of shows and classes on their website it’s easy for you to fit something into your travel plans to the beautiful city of Chicago.

Enjoy a night with friends and family and support the local artists who make gems like this place possible! Pro tip: They even offer student discounts on tickets to their shows so be sure to bring your school ID with you if are planning a visit!


The Second City

The Second City Picture Credits: The Second City


Opening its doors on December 1959, The Second City has since grown to become one of the most well known, and well-respected names in comedy. Having produced numerous comedy greats like Dan Aykroyd, Martin Short, Amy Sedaris, Tina Fey, and Aidy Bryant, this place is one of the world-renowned powerhouses of comedy.

They offer several shows per day with enough variety to make sure that anyone can leave grinning from ear to ear. If you’re looking for a date night that you won’t forget, I would highly recommend making an evening out of it here. And who knows, the comedians you see on stage just may be the next comedic geniuses of the next generation!


Virgin Hotel Chicago

Virgin Hotel Chicago Picture Credits: Virgin Hotel Chicago


Being called “One of the most inventive hotels in Chicago” by Zagat is no easy feat, yet it’s something the Virgin Hotel takes even minor details and makes them spectacular in a way you’ll have to experience to believe. Featuring the gorgeously designed Commons Club where Executive Chef Moosah Reaume serves up playful and inspired cuisine which all pair rather nicely with their cocktail menu which features 12 creative cocktails and a selection of beer, wine, and sake for those looking for something beyond the norm.

Don’t worry about splurging, since the hotel gym is also open 24 hours a day! Guests also frequent the Marquee space to check out a series of parties and events that rotate on a weekly basis. Check out the calendar on their website if you’re looking to get down!


Writers Theatre

Writers Theater Picture Credits: Writers Theatre


Having inspired and entertained audiences in Chicago for more than 25 years, Writers Theatre has become a pillar of the art community and a highly recommended place to see classics brought back in an inventive, and sometimes modern way. With more than 100 productions under their belt now (including 26 world premiers), Writers Theatre is the right choice for discerning audiences to enjoy one of the best drama companies around doing what they do best.

Known for their deliberately intimate performances and strong ties to the community you can rest assured that they will be sure to give you an experience you wouldn’t be able to enjoy anywhere else. Check out their website for information on their current and upcoming seasons and plan to spend an evening!


Fairmont Chicago

Fairmont Chicago Picture Credits: Fairmont Chicago


Surrounded by 400+ acres of protected park space, the Fairmont Chicago is a highly rated place to rest your head during your stay in the windy city.

Fully equipped with everything you may need like a 24-hour fitness center, spa, sophisticated yet welcoming bar, onsite taproom, and restaurant (with extensive beer selection), and 687 rooms and suites for you to choose from, this is the standard of quality and comfort you expect from a name like Fairmont. And even if all of that isn’t enough for you, they offer a highly knowledgeable concierge staff that would be happy to help guide to you some of the best sights and eats the city has to offer. Experience Chicago with all the comforts of home (and more!)


The Royal Palms Shuffleboard Club

The Royal Palm Picture Credits: The Royal Palms Shuffleboard Club


The Royal Palm is the place for lovers of shuffleboard or for anyone looking to find that relaxed vacation-in-Florida vibe without having to leave Chicago. Originally built in the 1900s as a space to house flower trucks, space is put to good use in the hands of owners Ashley Albert and Jonathan Schnapp, both of whom are internationally ranked, shuffleboard players!

The Royal Palms Shuffleboard Club now offers visitors plenty of space to play, mingle, drink, and enjoy the 20,000 square feet of airy, sun-drenched joy that will make even locals feel like they are on vacation! Don’t forget to check out the rooftop bar and of course the always rotating-selection of indoor food trucks. This place offers plenty of space to host your next event too for a truly unique experience you won’t soon forget.

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About the Author: Keith Perrotta

Keith is a freelance writer, English teacher, baker, and travel junkie currently based in Madrid, Spain. When not creating content or teaching ESL he enjoys going to the beach, researching bread recipes, looking through bookstores, and relaxing with a glass of wine. Having lived in the USA, France, Ghana, Kenya, and now Spain, his main goal in life is to visit every continent once (including Antarctica). You can usually catch him eating ice cream in the park or stopping someone in the street to ask to pet their dog.

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