Fun Things to Do in Chicago – The Ultimate Tourist Guide for Your Trip

Heading to Chicago and looking for some fun things to do? Chicago is a large city with lots of fun activities, famous attractions, diverse neighborhoods, and memorable things to do. Many people consider it one of the best cities in our nation.

Do Chicago how you want. Whether you’re traveling with kids-in-tow, planning a romantic getaway, meeting up with friends, or going solo, our helpful travel guides will help you make the most of your time in Chicago.

What are some popular attractions to visit?

  • Shedd Aquarium – The largest indoor aquarium in the world, with more than 8,000 aquatic animals from a range of diverse habitats.
  • SkyDeck Chicago – Offering amazing views spanning up to four states, and some of the best views of the city, from Navy Pier to Soldier Field.
  • Architecture River Cruise – Nothing is more impressive than this world-renowned architecture as seen from the Chicago River.
  • The Field Museum – Inspiring curiosity about life on Earth for more than a century. Come face-to-face with SUE, the world’s largest T. Rex, descend into an ancient Egyptian tomb, and much more.
  • Hop On Hop Off Chicago Bus Tour –  This Hhp-on hop-off double decker bus tour allows you to to explore Chicago at your own pace & get great views of the sights and popular attractions.

These are just a few. Want more fun ideas for things to do in Chicago? Head over here for more Chicago attractions to see during your trip.

How long are you visiting?

Whether you’re visiting Chicago for 24-hours or a long weekend, we’ve put together sample itineraries highlighting all the most popular things to do in the city.

From top-rated tours to the most iconic landmarks, these itineraries give you the best Chicago experience based on the time you have in the city.

Who are you visiting with?

No matter who you’re traveling with, whether it’s young kids or your significant other, there are a ton of things to do in Chicago for every type of traveler.

We’ve put together a list of top attractions and activities geared towards every type of traveler to help you start planning your trip.

What type of activities interest you?

Whether your travel goals are visiting all of the top museums and learning about Chicago’s unique history or simple to see all the most iconic spots, our Chicago local experts put together a few of their favorites to help you streamline your itinerary.

What parts of Chicago are you visiting?

Explore Chicago by neighborhood to make the most of your time sightseeing. We’ve highlighted a handful of top attractions and places to see by neighborhood in Chicago so you can maximize your time in each location.

When are you visiting?

Chicago is a fun city to visit year-round and offers a different experience to travelers with each season and type of weather.

Check out our lists of things to do in Chicago throughout the year to make the most of your itinerary and experience unique, calendar-based events when you’re in town.

What’s the best way to get around?

Chicago is easy to navigate. Neighborhoods are easily explored on foot (though can be far apart), there are tons of taxis and shared ride services available, and the public transportation system, known as the “L,” is very reliable and can get you just about anywhere.

Public transportation fare: Chicago Transit Authority (CTA) visitor passes, available in 1, 3, and 7-day increments, offer unlimited rides on all CTA trains and buses.  Check the CTA website for fare info, travel alerts, and trip planners. Most popular attractions are more accessible by bus than the L.

Tip: get the free moovit app for point-to-point trip planning and real-time updates for both subway and bus routes.

Taxis: taxis are available and easy to hail down and shared ride services such as Uber and Lyft are widely available and easy to use.

Hop-on hop-off tours: a hop-on hop-off sightseeing bus tour (an included attraction option) is a great way to get acquainted with the city. While it shouldn’t be relied on as transportation, it can be a fun way to get around to some popular attractions.

Looking for more info? Check out our post on getting around Chicago for tourists.

Where should you stay?

There are plenty of great places to stay in the area. Below are a handful of hotel suggestions located near popular tourist attractions and fun things to do.

  • Fairmont Chicago at Millennium Park
  • Sheraton Grand Chicago
  • The Westin Michigan Avenue Chicago
  • W Chicago – Lakeshore
  • Hilton Chicago- Michigan Ave Cultural Mile

Where should you shop?

In between sightseeing, try and find time to pick up some souvenirs. Here are a few popular areas to get some shopping in.

  • Macy’s
  • Macy’s State St.
  • Bloomingdale’s
  • Fashion Outlets of Chicago
  • Bloomingdale’s Home and Furniture Store

Make sure to check out all of the extra discounts and savings available on the Go Chicago Card.

Where to Eat

Go on a tour of Chicago’s foodie scene with this comprehensive list of family-friendly places to eat in Chicago.  We’ve included top picks for every appetite and even made note of nearby attractions so you can sightsee while you taste your way through Chicago’s culinary destinations. No judgement.

Fun Info from a Local

  • “The Bean” is actually formally known as “Cloud Gate.”
  • Route 66 starts in Chicago. Go ahead and get your kicks.
  • It’s not “The Chicago Bears,” it’s “Da Bears” – a term made famous by Bill Swerski’s Super Fans skit on Saturday Night Live.
  • The Field Museum is home of the world’s most complete Rex skeleton, its name is Sue.
  • The Chicago River flows backwards, thanks to modern engineering.
  • Chicago Lakefront Trail paths around Lake Michigan total 18.5 miles of beaches, playgrounds, fields, and more.

Share your adventure with us!

Tag us when you upload photos from your trip to Instagram: @SmartDestinations or #GoCityCard.

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