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Overrated Attractions in Chicago (and What to do Instead!)

As a local in Chicago, I’ve tried most of the traditional touristy things that the city has to offer. Whether out of curiosity, or because I had visitors in from out of town who wanted to try them, I’ve checked out all the highlights.

As with any city, some of the highlights are 100% worth doing. Sometimes the popular tourist attraction is popular because it’s awesome. But sometimes that popular tourist attraction is just a tourist trap. I’m here to tell you which things on the tourist trail to avoid, and give you local-approved activities to do instead!

Ready? Let’s go!

a view of the Chicago skyline from Lincoln Park

Skip: The Willis Tower

See: The Signature Lounge at the 96th

Update for 2024: Currently, the lounge and restaurant in the Hancock Tower are closed. Here's hoping a new restaurant takes up residence soon! Meanwhile, the 360 Chicago Observation Deck is still operating and, in this blogger's opinion, better than the Willis Tower.

There’s no skyscraper more synonymous with Chicago than the Willis Tower. (Sometimes referred to as the Sears tower, if you run into a particularly stubborn local!) It’s very natural to want to go to the top of the city’s most iconic building. The view of the city from the top is truly lovely.

But you know what your view of the Chicago skyline is missing from the top of the Willis tower? A view of the Willis tower! If it were me, I’d much rather seek out a different vista, so that that one famous building is actually in my photos!

So where should you go instead? Head to the northern end of Michigan Avenue and find yourself the Hancock Tower. (It's the tall black one with the two radio towers in the photo above!) The 95th and 96th floors of this building are a restaurant and cocktail lounge that are open to the public. The restaurant is profoundly expensive and often hard to get a reservation for, so I recommend the lounge. Depending on when you visit, there will likely be a line for the elevator. If you don’t feel like waiting, try to visit in the mid-to-late afternoon when the lines tend to be shorter!

When you get to the top, you’ll be seated at a table with a stunning view of the Chicago skyline. All of them have stunning views, but if you want a table right next to the window, you can tell your servers that and they’ll have you wait off to the side until one opens up. Once seated, you can order a drink or some small bites and savor both while you admire the city from above. Is this drink a little overpriced? Of course. But it costs less than a ticket to the top of the Willis Tower, and you get a drink and a better view!

Skip the Willis Tower. It’s the Hancock Tower all the way.

Skip: The Magnificent Mile

See: Andersonville’s Clark Street or the Southport Corridor

The Magnificent Mile, the catchy title for Michigan Avenue as it cuts through the near north side, is a shopping mecca. It’s a lovely street, full of gorgeous architecture and beautiful landscaping.

Locals never ever shop here.

Over 90% of the shops you can find on Michigan Ave are the same department stores you can find anywhere else. The remaining 10% are the designer boutiques that most of us can’t afford anyway. (Though if you’re looking for that designer gear, yes absolutely hit up the Mag Mile! Good for you babe! It's not an overrated Chicago attraction if you're here for a designer haul!)

Instead, for a more uniquely Chicago shopping experience, check out Clark Street between Foster and Bryn Mawr, or Southport Avenue between Roscoe and Irving Park. Both of these streets are home to eclectic shops and restaurants, most of them locally owned. This is where the locals do their adventurous shopping. I’ve done many a holiday season haul on Clark Street. You never know what kind of treasures you might find!

Skip: Navy Pier

See: The Chicago Waterfront

Tourists FLOCK to Navy Pier. Locals only go there when forcibly dragged. It’s essentially a giant overpriced mall, and it’s full of pickpockets.

For just about everything you’d want to do on the Pier, there’s a better place in Chicago to do the same thing. For instance:


See the previous points about the Magnificent Mile. Shop the Mile or find a local spot!


Everything on Navy Pier is overpriced, or a chain, or both. If you want a meal with a view of the water, try one of the many restaurants on the Chicago Riverwalk instead. I’ve got a guide right here just for that!

Boat Trips:

A lot of boat tours depart from Navy Pier, but the Architecture Cruises that leave from the Chicago River are a much better experience, and -bonus- you don’t have to go to Navy Pier.

City Views:

Yes, there’s a great view of the Chicago skyline from the end of the Pier. But the view from the parks around the Museum Campus is just as good. Plus you can go to a museum!

Ferris Wheel:

Ok, this is the one thing that Navy Pier has that you can’t find anywhere else. If you desperately want to ride the Ferris Wheel, do it, hold on to your purse, and get out when you’re done. Cheers!

Skip: Lou Malnati’s

See: Giordano’s

If there are any fellow Chicagoans reading this post I may have just picked a fight!

Deep dish pizza is another Chicago classic, and there are dozens upon dozens of places for you to track down a slice of good old fashioned Chicago-style pizza. These two restaurants listed here are local chains, and together they absolutely rule the Chicagoland area. Any Chicagoan, even the suburb-dwellers who like to call themselves Chicagoans, have a staunch appreciation for one (and only one!) of these two. It’s a turf war, and if you live in the area you have to pick a side.

For me, it’s Giordano’s. Hands down. No competition. The toppings are better, and the crust is infinitely more crispy on a Gio’s pizza. And a deep dish pizza has a looooooot of crust, so crust matters.

There are locations all over the city, so you will have no trouble finding one. Just be careful who you ask for directions, or you might get redirected to a Lou Malnati’s instead!

Why not try both so you can weigh in on the debate??

a view of the Willis tower in front of a cloudy sky

Skip all those overrated Chicago attractions!!

Want more info about all the best things to do in Chicago? I have a whole mess of local-approved Chicago Travel Guides right here!

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Love and Shenanigans,


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