6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (2023)

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (1)

So you’ve been planning a trip for weeks now looking at pictures on Instagram and Pinterest for inspiration and checking out TripAdvisor for top things to do in Chicago. There is absolutely nothing worse than getting hyped for a vacation and being thoroughly disappointed with your actual visit. To ensure you don’t go through the same feeling of frustration as me, here are top 6 Chicago tourist traps to avoid.

Before I get all you haters and Internet trolls telling me how great Chicago is… I THOUGHT SO TOO!

After seeing stunning photos from my IG friends @world.of.lina and @fromheretosunday, I was compelled to pay a visit. Now I did drop in during a November long weekend. Not exactly the warmest time of year for exploring Windy City. That’s on me. As much as I wanted to love my stay, I was completely underwhelmed.Maybe that’s just it with big cities during winter. It gets so cold and rainy that there’s not much to see. Although my trip this time didn’t leave me with fond memories of Chicago, I’m open to revisiting during the warmer months and exploring beyond just the popular touristy areas. If you are heading to Windy City any time soon though, watch out for these following Chicago tourist traps.

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Any online website (TripAdvisor, Time Out) or guidebook will tell you to check out John Hancock Center’s 360 Chicago observation deck. Tickets to the deck alone are$20.50 for adults 12+ but the real “fun” is at the Tilt.

It’s a supposedly thrilling experience where you step on a platform that will physically extend 45 degrees-ish out the building over the Magnificent Mile. You get a nice downward facing view of Chicago from1,030 feet up and tickets are an additional $7 (on top of that $20.50).

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (3)The Tilt as seen from outside the building.

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (4) 6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (5) 6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (6)

If you are afraid of heights, this could be a challenge for you. But as someone who’s lived on the 12th floor her entire life and enjoys epic views from building rooftops, this was a let down for me.I also haven’t been to the gym much since my car accidents and it honestly felt like a workout trying to push myself up against the window. The whole time I was supposed to be focused on enjoying the panoramic views,I was really thinking to myself damn I needa do more of ’em push ups! Lol!

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (7)View from 360 Chicago.

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Regarding Photography:

Although photos are not allowed during, the Tilt’s “professional” cameraman will help capture your special memories for you. I put professional in quotation marks because never once in my life have I seen a more expert photographer who has managed to click the shutter button at the exact moment when all his subjects have their eyes shut closed. One couple actually purchased their photo too. Not sure if they found it worth framing as a funny moment or if they are that lacking in the couple portraits department. Overall the entire experience was just an absolute rip off period.

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Yet another observatory type trap. Prior to my trip, Skydeck was the number one thing on my Chicago bucket list. Having been to Toronto’s CN Tower and Calgary Tower’s glass floor observatories, I was ready to challenge myself to Willis Tower’s103rd floor glass balcony. And of course, my Instagram profile could use some aesthetically pleasing window shot.

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (11)Elevator line to get up to the observatory.

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (12)Lineup for the Skydeck glass balcony.

Their website suggests getting there right at opening around 10AM to avoid crowds. Boy let me tell you………….. We arrived around 9:45AM and people were lining up already. This was a MONDAY!Again, yes, I visited during a November long weekend – Remembrance Day (Canadian)/Veterans Day (American) to be exact. Although it was a long weekend for us Canadians, last time I checked, Monday was not a stat holiday in the States. I doubt November is peak season either. Where the hell did all these people come from!?!??!?!??!?!?!??!?! I had all these cool photography ideas planned in my head but nope, dreams shattered.

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (13) 6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (14) 6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (15)View overlooking the other balconies.

The Process & Experience:

When we first lined up, it was one line per glass balcony (there are four in total). When it was almost our turn, the line got split into two. Now we lined up twice to take pictures since you obviously don’t get enough time. The first time round was cool. We got to enjoy the entire balcony to ourselves regardless. The second time round we went to a different balcony and it was shared between the two lines i.e. you really only got a tiny corner. Don’t forget, tickets are $23.00 for ages 12+. Whereas CN Tower or Calgary Tower grant you unlimited time to enjoy your experience, Skydeck literally only gives you a few seconds for pictures and that’s it.No time to actually enjoy the view or take in the fact that you are 103 stories above ground and you’re standing on a floor made of glass whatsoever.

Frankly speaking, I didn’t want to include this on this list. It’s definitely worth a visit if you’ve never been to these glass-bottom type observatories, but after comparing it to my previous experiences, I say you could spend that money elsewhere and have more fun with it.

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (16)6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (17) 6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (18) 6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (19)The above four photos are views from different angles of the observatory – not the glass balcony.

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Pizza? Really????? But you could never go wrong with pizza! Or so I thought…

I took to Instagram in asking what I should do in Chicago and the lovely Miranda and a couple other ladies all suggested trying deep dish pizza. And what’s more iconic of this Chicagoan dish than Giordano’s Pizzeria established in 1974.

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (21)6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (22) The pizza looked a lot taller/higher in photos I’d previously seen online.

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Okay, I have a confession… When asked how my experience was from friends who’d recommended Giordano’s, I was a little reserved and said the first bite was amazing but the rest was too heavy for me. The truth is, from the very first bite of that extremely overfilled cheese stuffing, I was… well… a little disgusted? It was intensely rich (in a bad way) and I could feel my arteries clogging up. Who knew too much cheese could be a bad thing!? I didn’t want to say this to them because I felt bad they took the time to suggest something nice. I couldn’t bear to bash on this dish that really isn’t even their fault it didn’t taste good. So here I am, a hypocrite caught in my own white lie. If y’all are reading this, I’m sorryyyyyyyyyyyy girls. Maybe I’m just a weirdo who doesn’t like extra cheese.

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (26)~20 minutes since the waitress brought the pizza and it was still sizzling hot. Would you look at that cheese go!?

6 Chicago Tourist Traps to Avoid - My Suitcase Journeys (27)Pretty much everyone who dined here left with a bag of leftovers in hand.

My friend and I ordered the small size which came with 6 slices. We barely finished the one slice the waitress cut and served us and got the rest packed to go. The branch we went to was in the Loop/Millennium Park area and the place was packed! We were told the wait would take an hour and we would be contacted via text. Great thing about dining here is we got to stroll the Millennium Park to kill time. The wait ended up only taking 45 minutes. Even though we pre-ordered when we reserved seats, we still waited a good 10-15 minutes after we were seated before getting our food.

Final Verdict:

If you’re a mad cheese lover, this might be your jam. (Although don’t expect to be tasting some high quality, finely aged cheese.) If not but you still want to try one of Chicago’s most iconic dishes, either order the individual 6″ one and share with a friend or don’t bother because you will feel like crap after. Would I try deep pizza again? Never. Not even if I were wasted and craving super duper heavy, greasy food would I ever put myself through this.

While we’re on the subject of food, let’s talk about another one of Chicago’s famous foods – hot dog.

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I first heard about Portillo’s from Buzzfeed’s Worth It series where they tried three different hot dogs at three drastically different prices. They also have a whole separate article on it over here – “If You Haven’t Had Portillo’s Yet You’re Missing Out.”

The restaurant kinda reminded me of a market type food court scene. You line up, order, pick up your food in a separate line, and find a table yourself. Not really a restaurant even but you gotta remember, this1963 legend first started its business in a trailer.

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I wouldn’t say their hot dog tasted terrible.My friend tried the chilly dog and she said it was great. Me, I went with the original. Just a plain poppy seed bun with mustard, relish, celery salt, freshly chopped onions, sliced red ripe tomatoes, kosher pickle, and sport peppers. The pickle is what makes it special. Classic Chicago style hotdog and the Chicagoans actually call this “dragging the dog through the garden.”

Why It’s A No:

From where we were staying, Portillo’s was a little awkward to get to. It was far to walk to in the cold, but bussing essentially took the exactly same time too. I feel like when something getshyped up so much, you start creating this augmented illusion in your mind about how great it would be. You become blinded to what it really is and truth is, a hot dog will always be just a hot dog no matter what. Sure it’d be a nice snack for a baseball game. Heck it’s a hot dog! Not worth the trek to get to.

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Call me a hater, but I don’t believe in wasting time shopping when abroad on trips. Europe is a whole other situation because buying luxury goods, for example, would obviously be cheaper there. Chicago, however, I don’t see what people are raving about for Magnificent Mile.

Sure, you got your Canada Goose. Even here in Vancouver we don’t have a Canada Goose store. Although Magnificent Mile is more of a luxury shopping street, you still have your typical Forever 21, H&M, and Victoria Secret, etc. If you are spendingsay $500 on airfare, you are not going shopping at some ordinary shop you can find back home. Skip it!

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This last one is a more or less a winter’s edition only.

Like I said, my visit was in November. I got so many suggestions for hitting up Buckingham Fountain but we all seemed to neglect the fact that Chicago is cold AF in the winter. Ain’t no fountain gonna be running in the butt freezing weather. Oh and the trees are also all dead in the park. It’s close to the waters as well so the wind is especially chilling to the bones. Visiting in the summer? Yes, definitely visit. Have a picnic in the park, play frisbee with your friends, hell yes. Visiting in the winter? Skip!

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That’s it for this week!

There you have it, top 6 Chicago tourist traps to avoid. This is probably the first post where I’ve given so much honest and humble opinion (ahem hate) on a subject. Every traveller is different. Even though I didn’t necessarily enjoy all of the places listed above, you may beg to differ. Again, weather played a big part too. If it wasn’t so gloomy, I might’ve enjoyed Chicago 360 more for instance. You never know! Take everything you read on the Internet with a grain of salt.

For more tips on Chicago sightseeing and a complete 48-hour Chicago itinerary, be sure to read up on my post for “How to Spend the Perfect Weekend in Chicago“.

Last but not least, my apologies for the grainy photos. I’ve only noticed now that my mirrorless camera performs extremely poorly under low light situations. Biggest regret of mine switching from Nikon to Fujifilm. If you have any recommendations for a nice intermediate to expert-level camera, comment away!

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