Chicago Tourist Traps to Avoid: Unmasking the Windy City

Chicago is a vibrant city full of famous attractions that draw tourists from around the world. However, some of these popular sites have become overrun with crowds and long lines, turning them into tourist traps.

Follow along as we list down some Chicago tourist traps to avoid for travelers seeking a more authentic Windy City experience.

Tourist traps are synonymous with hordes of visitors, interminable queues, and underwhelming experiences. It’s all too easy to become frustrated and aggravated when trapped amid throngs of fellow tourists.

Should you feel yourself getting overwhelmed at any of Chicago’s crowded attractions, pause and take a deep, calming breath. If your goal is to enjoy an adventure beyond the swarm and revel in the city’s true spirit, consider skipping these six popular places in Chi-town.

Cloud Gate (aka The Bean)

If you look up Chicago tourist attractions online, you’ll find Cloud Gate, also known as “The Bean,” on every list. This gleaming sculpture draws over 20 million awe-struck visitors a year to Millennium Park.

Now, while its mirrored surface and reflections of Chicago are pretty cool, dealing with the huge crowds around it can be a bit annoying. Trying to take a good picture becomes a challenge with all the selfie sticks, families passing by, and people glued to their phones.

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Unless you show up early in the morning or late in the evening when it’s not as busy, getting a photo without the crowd is tough. But don’t worry!

Instead of fighting through the Bean chaos, you can check out other cool artworks in Millennium Park and nearby. There’s the colorful Crown Fountain and the tall sculptures in Maggie Daley Park.

But, if you’re really set on getting that perfect Cloud Gate photo with the clouds, just go early or late and be patient!

ground view of people walking past cloud gate bean in Millennium Park in Chicago, Illinois, USA
phot credit: Cloud Gate via Facebook

Magnificent Mile

The Magnificent Mile might sparkle with fancy stores and restaurants, but the huge crowds make it a top Chicago tourist trap. Loads of people visit this famous shopping street for everything from high-end brands like Gucci to more casual spots like Gap.

The sidewalks get packed with slow-moving window shoppers. If you’d rather not deal with the slow crowds, skip the Mag Mile and check out other cool shopping areas in Chicago instead.

There are indie boutiques in Andersonville, great deals at Fashion Outlets of Chicago, or the glam vibes at Water Tower Place. And if you’re into unique places to visit in Chicago, explore different neighborhoods.

Pilsen has awesome murals, and Oak Park is filled with green streets and architectural wonders by Frank Lloyd Wright. Avoiding the Magnificent Mile crowds lets you experience the real shopping and culture of Chicago.

The Magnificent Mile Buildings from ground with taxis and pedestrians in Chicago, Illinois, USAObservation Decks

Not a fan of heights? No need to worry about falling into this Chicago tourist trap! But for those who enjoy being up high, visiting the city’s observation decks like the 360 Chicago Observation Deck might sound like a great idea.

After all, who wouldn’t want to see the Windy City from high above? However, besides dealing with big crowds, some might think the tickets are a bit pricey for just looking at the skyline. That’s why many visitors decide to skip the observation decks.

But hold on, that’s only true if you don’t do your homework! If you’re an early bird, a night owl, or just good at finding deals, these tall spots are still worth checking out. Get up before sunrise or wait for sunset to avoid the biggest crowds, and grab discounted tickets on Tripster for 25% off.

With some research and planning, you can enjoy fantastic views of Chicago without the hefty prices or huge crowds. Because, you know, these towers do deliver the goods if you know what you’re doing!

people on tilt at 360 chicago
photo credit: 360 CHICAGO via Facebook

Navy Pier

Navy Pier is packed with big-name chain restaurants and amusement park stuff, making it kind of like Chicago’s version of Times Square – a classic tourist trap. Families head there for rides and kid-friendly stores, filling up the sidewalks with strollers headed to places like Build-A-Bear or the Children’s Museum.

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But behind all the people taking selfies and the sugar rush from snacks, you find a pretty dull sameness, almost like an airport food court. If you’re more into feeling the real vibe of Chicago than hanging out in what feels like a big mall, then just skip Navy Pier.

Check out the blossoming trails along the Chicago Riverwalk, try out food from 20 different neighborhoods, or kick back in a genuine blues club away from the usual spots.

Navy Pier gives you just a surface-level taste of what this lively city has to offer. So, avoid the tourist traps in Chicago and dive into the unique and tasty parts of the city.

close up of navy pier ferris wheel and swings with fountains in the foreground in Chicago, Illinois, USADeep Dish Pizza

Truth be told, deep dish pizza is like Chicago’s ultimate food treasure, but popular spots like Giordano’s and Gino’s East often make you wait for ages, testing your hunger. Sure, their famous pies cooked in iron skillets are mouthwatering.

However, smart food lovers know that lesser-known places like Pequod’s serve up the same deliciousness, sometimes without the long lines. If you’re a traveler who doesn’t want to deal with intense queues, even for Chicago’s iconic pizza, you might want to consider embarking on an exciting food tour such as:

These tours, led by experienced guides, take you to hidden gems in the city’s coolest neighborhoods. With so many restaurants, it can be overwhelming to choose, but by joining these food tours, you can avoid the typical Chicago tourist traps.

Deep Dish Pizza at Giordano’s - Chicago, Illinois, USAArchitecture Boat Tours

Chicago is renowned for its world-class architectural wonders, and while boat tours along the Chicago River are a popular choice, they can be a bit pricey. If architecture isn’t your cup of tea or you find it hard to catch the tour guide’s words over the boat’s hum, you might end up paying a lot for what feels like a snooze fest.

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Fear not! Opt for an unconventional tour focusing on Chicago’s diverse neighborhoods or delve into topics that genuinely spark your interest, like art, cuisine, or history. If architecture is your passion, don’t worry about breaking the bank.

There are plenty of affordable architecture tours that let you explore Chicago’s structural marvels without denting your travel budget. So, skip the standard boat tour and dive into Chicago attractions with a tour that truly speaks to your interests.

A Spirit of Chicago dinner cruise is an excellent way to spend New Year’s Eve in ChicagoHelpful Tips Before You Go

Visit at an Off-Peak Time

Timing is everything when it comes to visiting Chicago’s attractions. By doing a bit of research, you can figure out the peak and off-peak times for these hotspots. Tools like Google listings can be super handy for this!

Discover when the crowds are at their peak and lowest, and plan your trip accordingly. To make this easier for you, check out our guide on When is the Best Time to Visit Chicago?. It’s got all the insights you need to ensure you make the most of your visit without getting caught in the tourist rush!

Grab Attraction Passes

Get insider access to Chicago’s top attractions with the Go Chicago Explorer Pass. This discounted pass offers savings up to 35% off admission to over 20 popular sites like the Art Institute, Field Museum, and Museum of Science and Industry.

Valid for 30 days from first use, the pass allows you to experience Chicago at your own pace. See the stars at the Adler Planetarium one day, immerse yourself in aquatic wonders at the Shedd Aquarium next.

For maximum Chicago sightseeing flexibility, consider the Go City Chicago All-Inclusive Pass. This pass bundles admission to over 40 Chicago attractions, tours, and experiences into one value-packed package.

From prestigious museums and exciting tours to cruises, zoos and beyond, the All-Inclusive Pass grants access to all your Chicago favorites. As you plot your Windy City adventure, the pass will help you save money while creating rich Chicago memories across this dynamic metropolis.

Book Tripster’s Vacation Packages

Skipping the line is every traveler’s dream when visiting popular attractions. Fortunately with some advance planning, you can bypass lengthy ticket queues and unlock significant savings in one fell swoop.

Related Post: Unique Chicago IL – 26 Most Interesting Things to Do

Purchase admission to your chosen Chicago sights ahead of time online to breeze right in upon arrival. For maximum convenience and affordability, bundle your Attraction tickets with Hotel stays as part of Tripster’s Chicago Vacation Packages.

By plotting your itinerary and locking in deals early, you’ll be rewarded with both time and money savings. Savor more moments in discovering Chicago rather than waiting in the winds!

Break Free from Chicago Tourist Traps

Escape the chaos of crowded spots and discover the genuine soul of Chicago in all its diversity. Avoiding tourist-packed places gives you the freedom to explore at your own pace – to experience Chicago’s dynamic personality through its different neighborhoods.

Connect with locals, share their favorite hidden gems, and dive into off-the-beaten-path eateries or bars. Choosing your own adventure, driven by authentic curiosity instead of a rushed tour checklist, allows you to unearth a more real Chicago.

This is the genuine Chicago – not the glossy brochure version hidden behind turnstiles and ticket booths, but a living Windy City that rewards the bold. So, gear up for the adventure with Tripster today!

Witness the true spirit of Chicago unfold – in all its easygoing, unfiltered, and crowd-free glory!

Have Any Tips to Add?

Which Chicago tourism spots would you add to our list? Tell us in the comments!


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Written by Archie Villaflores

Over the years, he has won numerous national contests for news and editorial writing, but he has recently discovered that his true passion...


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