Chicago is known for an array of dining options, champion sports teams, incredible arts, dozens of museums, and over 300 parks. In fact, Time Out rated it the #1 World’s Best City for Having it All!

Located in the Midwest and the third-largest city in the U.S. – Chicago (aka Chi-Town aka Windy City aka Chicagoland) has been at the top of my “must revisit” list for over 6-years.

The first time I traveled to Chicago, I was 20-years old. It was uneventful considering I didn’t technically stay in the city and was with a super lame boyfriend. Glad that ended. . . in Chicago. I broke up with him in Chicago. But he did make me a Bears fan, so thanks. Da Bears Da Bears Da Bulls!

The second trip was way more exciting. I attended my first ever Cubs game, ate my way through the Taste of Chicago, and spent Independence day enjoying fireworks over Lake Michigan. It was the trip that won me over and I’ve been trying to return ever since.

Fast forward 7 years and my wish finally came true. I got to spend a perfect 3-day weekend in Chicago with my current boyfriend. Don’t worry, we’re still together.

Luckily, it felt like the first time again for so much had changed. We rushed to do as much as we could without preventing us from enjoying the moments.

PRO TIP: Travel at a pace that lets you enjoy the moments. Not snap a picture while thinking about all the other stuff you have to rush to see. That’s not what good traveling is about.

This post is specifically for unique forms of entertainment. I will warn you, we only grazed the surface for there are so many unique and exciting things to do in Chicago. A weekend is hardly enough time. If it’s your first time in Chicago, my advice would be to make your trip at least 4 days.

4 days in Chicago is a good amount of time to visit top attractions, eat plenty of food, and have time to explore the unique, lesser-known parts of the city.

Should you still go even if you can only get the weekend off? Absolutely!

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Psst. . . Looking for more weekend getaways around the U.S? Check out a few of these posts:

• Long Weekend in Austin: Food, Art, Booze & Music

• What to do in Seattle for a Weekend: Food, Nighlife & Attractions

• If You Like Fun, This is Where to Go in Denver

Q&A First Time Visitors

What is the best time to visit Chicago?

Chicago gets extremely cold in the winter months. Duh! Everyone knows that by now. Locals will repeatedly tell you winters are cold but summers are amazing! Guess that’s why they haven’t all fled the city. The reward of summer outweighs the cold of winter. I have officially traveled to Chicago every season and can confidently tell you the best time to visit Chicago would be July through October.

OK June is good too but here’s why I think July is even better. . .

In July, though humid, you have the Taste of Chicago which is a 5-day celebration of food! Sample the diverse array of local cuisine, dance to live musical performances, and join in on the many activities. It’s only the world’s largest food festival – no big deal.

August brings another world-famous event – Lollapalooza. A music festival featuring over 170 artists on 8 stages with food, drinks, and activities galore. I just realized I say galore a lot. Is that word even cool anymore? Oh well, galore.

Following the beauty of Summer, comes the beauty of Fall. The leaves change into gorgeous colors.

If you’re looking for incredible photo ops, Fall is without a doubt the most beautiful time to visit Chicago.

How safe is Chicago?

The quick way to answer this is to say “Practice common sense and you will be just fine”. I get it. Unfamiliar places inherently make us feel unsafe. Not knowing what street your on and relying solely on Google Maps and good cell signal is not always the best feeling. It’s not like Google knows what areas to avoid.

That’s why you should 1) opt for Uber or Lyft if you’re out late, and 2) stay clear of the South Side. However, if you’re spending most of your time in the Loop you will be fine. More than fine. You will be great because you’re in a fantastic city. My recent visit to Chicago was for a three days.

I admit I’m not an expert on all unique things in Chicago. That will come with a few more trips, which are planned. Yet, what I did find was amazing, and I hope you find yourself experiencing them too.

Tips for Visiting Chicago Attractions

The only tip that matters is to save money and purchase the CityPASS. We used the Chicago CityPASS which made visiting top attractions significantly cheaper. Plus you get sweet VIP entrance so no waiting in line, well long lines. Click the link below if you want to read my full review.

If you don’t plan on taking public transportation to all these places, then budget $200 for Uber/Lyft. This includes to and from O’Hare which run around $30 each way. One thing I like to do is check Ibotta and credit cards for cashback offers and deal on Uber or Lyft. They almost always have them.

Psst: Looking for ways to save for travel? Check out my favorite money-saving tips.

Science and Space Rule!! Don’t mind me geeking out but I do love the topic of space. The Adler Planetarium in Chicago is special because it’s America’s first. Founded in 1930 by Mr. Max Adler. Today it remains a great place for learning and exploring our galaxy and those far, far away.

I watched the 30-minute Cosmic Wonder show that takes viewers way up in the Chicago night sky to explore the constellations. Sadly, no photos are allowed during the show but you can take my word for it. We’re friends, right? So trust me when I say this show is out of this world! There are a few other shows I would have liked to see such as Destination Solar System. You can view all their shows and more here.

Need to give your feet a rest?

Why not schedule a show in the middle of your busy day? You get to learn something, check a spot off your Chicago Bucket List, and rest yo’ feet.

#2: Experience Chicago Style Magic

The Chicago Magic Lounge is my top choice for most unique things to do in Chicago. It was our most memorable experience. Located in the quirky neighborhood of Andersonville – one of the most diverse neighborhoods in Chicago. Before the show, I highly recommend you spend time walking around Andersonville, stopping in one of their specialty bakeries or boutique shops. I’m going to do my best to explain the magical evening without giving too many spoilers away.

From the moment you arrive, you will already be confused by their rather secret entrance. If you think you’re in the wrong place, you’re probably in the right place. Enter through the secret passageway to the main bar area where magic lives both behind the bar and in the delicious concoctions.

What does that mean?

It means a magician is performing tricks from behind the bar that will leave your mind in a confused state. No, it’s not the liquor toying with your mind. It’s magic!

I can’t recommend enough that you arrive early – giving yourself enough time to explore the bar, magic library, and yes, even the bathroom. The bathroom has a rather impressive illusion. One might even be reluctant to step over the black hole. All this and the show hasn’t even begun!

The usher will announce in the bar when it’s time to grab your seats. Your entrance to the theater will be rather surprising too, but that I can’t tell you. I just can’t.

The Show

We saw the 7:30 signature show. At the time of writing this post, show tickets range from $40-60. Check prices and availability here and see for yourself.

Once you take your seats the server will come around to take your drink and food order. At the same time, magicians are walking around, entertaining guests with card and coin tricks. It was up close and personal which I loved. By the time the show started, I had already had a personal encounter with the acts.

The acts were HILARIOUS and incredibly MAGICAL. Fooled me once. Fooled me twice. Yup, I have no idea how they did it. I have to say the host was delightful. He had me laughing all show.

Food & Drinks

I got the Abracadabra first then switched to old fashions. I know I can’t help it. Old fashions are life and theirs did not disappoint. So I got another one 😉 Food hit the spot too. We arrived hungrily and ordered every small plate on the menu.

A WORD OF ADVICE: The menu consists only of small plates, so I urge you to eat dinner before the show.

The “After” Show

If you purchase the Mezzanine Experience you will have access to a bonus show which takes place in the 654 Club. This theater is smaller but cozy. The closeness between magician and crowd felt less big stage production and more like a room of friends watching our talented friend drop some mind-blowing magic tricks.

Of all the acts of the night, the craziest ones wherein the 654 Club.

The City Winery, located at the Riverwalk is so cool and a must-visit if you’re a vino drinker. Bubble wine. Bubble, bubble, bubble wine. Everyone! Ok, I’ll save my singing for the vlog. Which reminds me… .are you subscribed to my YouTube channel?

Shameless plug. But seriously, I briefly film the City Winery, giving you an even better idea of how cool it is.

They host many events from live music to champagne nights. Be sure to check out their Instagram for up-to-date info.

Back to the bubble.

The tables outside are enclosed in a clear bubble dome. It’s the perfect spot for socializing with new and current friends while enjoying the breathtaking views of downtown Chicago from the river. The location couldn’t be more perfect.

No weekend in Chicago is complete without trying both Chicago Style pizza and Chicago Dogs. For your deep dish pizza fix head to Giordano’s – a chain frequented by tourists, especially the one outside of Skydeck, however, it’s amazing. Though a chain, it’s still authentic Chicago Style Pizza.

When I stopped to ask a local if this place was over-hyped or if he would eat there himself, he proceeded to tell me that it’s busy because it’s the best. However, I enjoyed Gino’s East more. I also recommend Lou Malnati’s Pizza. Someone stop me. I can talk (and eat) pizza all day long. For more delicious pizza options, check out this post on authentic Chicago deep-dish places you need to try.

As for Chicago Dog. I’m going bold and saying anywhere delivers. I have yet to step into a place of business, order a Chicago dog, and find disappointment. I’m starting to think it’s just impossible.

Please, if you have found THE BEST CHICAGO DOG let me know in the comments below.

#5 Tilt Over the Side of a Skyscraper

Skydeck is the observatory located on the 103rd floor of the Willis Tower. Many come for their chance to step out on the ledge. extending 4 ft. out the side is a glass balcony. Visitors can step out and stare 1300 feet straight down, or if you’re like me, crawl out and take a lil’ nappy poo. It also happens to be one of the most incredible spots to watch the sunset over the city.

360 Chicago takes the thrill to a whole other level. Located on the 94th floor of the John Hancock tower 360 Chicago offers so much room for activities including the insane Tilt – a ride that tilts your ENTIRE body 45 degrees over the ledge of a skyscraper. 1,000 feet up to be exact.

They also host tons of activities including the Thursday night Hoppy Hour from 6-9 pm. Visitors can sample crafts from local  Revolution Brewing, entertain with bar games, and enjoy epic views.

REMEMBER: Both of these attractions are included with a CityPASS purchase.

#6 Flick a Giant Bean

Or at least create the illusion. This is easily one of the most iconic spots in Chicago. Everyone around the world recognizes The Bean. But did you know the official name is Cloud Gate?

Visitors can walk under and around this unusual sculpture while viewing the city around them in a warped state. When there’s not a swarm of tourists around you it makes for a fun photo challenge. Nevertheless, it’s an incredibly unique work of art unlike anywhere else.

PRO TIP: Beat the crowds by arriving super duper early, or toughing it out during the cold winter days. I think a snowy backdrop to your bean reflection photo would stand out from the other 99%.

More Unique Things to do in Chicago

Because I love you so much, here are even more unique things to do in Chicago this weekend that come highly recommended by locals.

Underground Tunnel Tours: The lesser-known side of Chicago lives in the tunnels. Many visitors come and go without ever discovering the world below. The tour will guide you through the history of the tunnels. It’s truly remarkable.

Green Mil Lounge: What once was a speakeasy for Al Capone himself and all his friends is now a must-visit for both history buffs and ghost chasers. Al Capone was a frequent visitor of this joint which many believe still is. That doesn’t stop this notorious joint from serving booze and jazz music all night long.

Taste of Chicago: Attending the world’s largest food festival is unique and can only be done in Chicago.

Lollapalooza: If you’re a music junkie then Lollapalooza needs to be on your music festival bucket list. This too takes place in Grant Park which is located in The Loop.

Book your hotel well in advance. Check here for the latest ticket sale info.

Visit the award-winning Chicago Shakespeare Theater. It’s a non-profit theater on Navy Pier with incredible shows happening all year long.

Eat a Michelan Star meal. It’s no secret Chicago is one of the food captials of the world. If you’re looking for an incredible place to eat then consider making a reservation at one of Chicago’s finest like Sixteen.

Looking for a romantic side of Chicago? Read this extensive guide on Romantic Getaways in Chicago, as well as, surrounding cities in Illinois.

Totally Adorable Hotels in Chicago Loop

If you’re looking to hit up all the top spots such as Miracle Mile, Grant Park, etc. – staying anywhere in the Loop is best.

The Loop is the name given for downtown Chicago and covers a huge area. I’ve stayed in three different hotels around the Loop and have enjoyed them all.

Publishing House Bed & Breakfast is considered the West Loop and was incredible. It’s a super hip super modern B&B but feels more like a hotel. New as in it opened in 2017.

You can read my full review here.

I also stayed at the Kimpton Allegro centrally located in the Loop. Ahh, this hotel is so beautiful. It was hard to believe I was staying there. If you love that dark and mysterious, gold and delicious Gatsby vibe with classy cocktails then Kimpton Allegro will instantly win you over.

The last worth mentioning is the Hyatt Centric Chicago Magnificent Mile. Just a short walk from top attraction and world-class shopping on the Magnificent Mile. Or is it Miracle Mile? I’ve heard both. The hotel is modern, reasonably priced, and clean. If you’re looking for big-city living then this makes for a perfect trial run.

Booking.com