The Most Important Things You Need To Know About Chicago: A Tourists Guide

If you’ve never been to the windy city, it’s time you stop lallygagging and plan a trip.

1. Ahhh, the Windy City…


Chicago is one of the best cities in the world, according to most. We have everything you could ever need: entertainment, food, an awesome transportation system (the L), and beaches!…most people don’t know about the beaches. The following is a tourists guide to the city, complete with pictures and awesome tips. Enjoy!

2. The food


Chicago is one of those cities with delicious signature foods that you definitely have to try if you’re ever in the city. In fact, our food is so iconic, that other cities try to duplicate the awesome by having Chicago-style offerings on their local menus.

Chicago-Style Hot Dogs

What’s not to love? This Chicago staple has everything you could ever want in a bun.

Where to get it: Superdawg, Portillo’s, The Wieners Circle

Deep Dish Pizza

Just look at that cheese and the sauce and the thick THICK crust….everyone has their preference and their opinion of the “best” pizza in the city, but lets be real - it’s all delicious.

Where to get it: Girodano’s, Gino’s East, Lou Malnati’s

Italian Beef

I’ve never met an Italian Beef sandwich that I didn’t like: The meat, the peppers, the seasonings and the bread. This Chicago staple really knocks it out of the park.

Where to get it: Al’s Italian Beef & Portillo’s

3. Shows


From improv to sketch to stand up to blue men, Chicago has shows going on all over the city seven nights a week.

4. Comedy

Chicago is known for its comedy scene, and even more so for its improvisation. Young, hopeful comedians/improvisers from all over the country and the world come to Chicago to pursue their comedy dreams. On any given night you can see sketch, improv, or stand-up at various theaters and venues across the city. The number of famous comedians that have gotten their start in Chicago is exhaustive and is nothing to laugh at (pun totally intended). The best part is that these theaters offer classes, so if you want to try your hand at comedy, it is a very easy community to get into. Who got their start in Chicago?:Tina Fey, Amy Poehler, Steve Carrell, Bill Murray, Chris Farley, etc etc.

Where to see shows: The Second City, iO theater, The Laugh Factory, Zanies.

5. Blue Man Group

Have you ever wondered what it would feel like to trip on ecstasy, but be totally okay with it? That is the experience you’ll get if you go see The Blue Man Group. The show combines, music, video, audience interaction, paint, toilet paper, and marshmallows all brought to you by weird blue dudes who never say a word, to create a one-of-a-kind experience that no other entertainment group can offer. They have shows several times a week and no two shows are exactly the same.

Where to see it: Briar Street Theater

6. Broadway

Chicago has had a number of critically acclaimed broadway shows come through the city over the years. Whether you enjoy comedy, drama, musicals, you-name-it, Chicago has it. Shows are offered every night of the week at several different venues. Chicago has been graced with the presence of: Rent, Chicago, West Side Story, Wicked, The Lion King, and most recently The Book of Mormon, which has extended it’s Chicago run twice due to high demand.

Where to see shows: Oriental Theater, Cadillac Palace Theater, Bank of America Theater, Auditorium Theater, and the Broadway Playhouse

7. Museums & Culture


I’m a big nerd so I LOVE going to museums and learning a thing or two about a thing or two. If you’re like me and share my love of knowledge then there are plenty of things to do in Chicago to quench your intellectual thirst.

8. The Shedd Aquarium

It’s unfortunately been years since I’ve been to the Shedd, but from what I hear it’s still just as amazing as it always was. With fun activities like a dolphin show and an exhibit where you can pet stingrays the Shedd will undoubtedly provide something fun for everyone in your group. It is also situated on Lake Michigan and is completely surrounded by windows, so the views are nothing to scoff at either. The museum also offers free days, so if you’re ever in the city, this is definitely something to check out.

9. Navy Pier

Navy Pier, home of the Chicago Children’s Museum, IMAX theater, and a giant ferris wheel, what else could they possibly offer? How about restaurants, stores, and boat tours. Not only that, but thousands of people flock to Navy Pier every year to see their fireworks displays on the 4th of July and New Year’s Eve.

10. The Field Museum

I don’t know any child who didn’t go to the Field Museum for field trips when they were in school. In fact, you at least went once a year, and sometimes even twice or thrice. The exhibits at the Field Museum rotate out, so there is always something new to go see. Some of the past exhibits have featured: Sue the T-Rex, Chocolate Around the World, and Real Pirates. Like the Shedd Aquarium the Field Museum also offers free days, so really what have you got to lost.

Other museums to check out (that ALL offer free days): The Museum of Science & Industry, The Chicago Art Institute, The Museum of Contemporary Art, & Adler Planetarium

11. Sporting Events


No matter your favorites sport, Chicago has a team whose jersey you can don and name you can proudly chant from the crowded arena.

12. The Teams

Chicago is home to two baseball teams, two hockey teams, a basketball team, and a football team. Which means, that at any point in the year you have a Chicago team for which to root. Wrigley Field is home to the Cubs, US Cellular Field (formerly Comiskey) hosts the White Sox, Soldier Field is where the Bears can be seen dominating the Packers, AllState Arena hosts the Wolves, and The United Center is home to the Bulls and the Blackhawks. Phew…that’s a whole lotta sports.

13. Sights and Attractions


Like any major city, Chicago has several tourists attractions that draw thousands of people every year.

14. The Sears Tower Skydeck

Located on the 103rd floor of the Sears Tower* this observation deck is 1,353 above the ground and not for the squeamish or those that are afraid of heights. Just looking at the picture can make your stomach drop.

  • They tried to rename the Sears Tower the Willis Tower a few years ago, but tried and true Chicagoans refuse to accept the change and still refer to it by its appropriate name.

15. The Bean

Located in Millennium Park in Downtown Chicago this sculpture actually title Cloud Gate and affectionately nicknamed The Bean is one of Chicago’s most popular tourist attractions. Every day hundreds of people can be seen taking their photograph in front of the giant steel sculpture inspired by liquid mercury.

16. Buckingham Fountain

This Chicago landmark located in the center of Grant Park is one of the worlds largest fountains. It operates from April to October, with regular water shows and evening color-light shows. During the winter, the fountain is decorated with festival lights.

17. Festivals & Events


Every year Chicago hosts a plethora of events that people travel for miles to attend. Here are some of the best.

18. The Taste of Chicago

Remember the food I mentioned previously in this post? This week-long event hosted in Grant Park allows thousands of people to sample the best food that the city has to offer. With hundreds of food vendors from all over the city you’re sure to discover some new foods and favorite restaurants.

19. Lollapalooza

A music-lovers wet dream, this 3-day long festival hosts 100+ music artists. Some of the headliners include: Lady Gaga, Red Hot Chili Peppers, Mumford & Sons, The Killers, The Smashing Pumpkins, The Ramones, Daft Punk & Pearl Jam. No matter what your musical poison, Lollapazlooza, affectionately known as “Lolla” by its faithful attendees, will have more than enough music for you to enjoy. It’s also all completely outside, which is a pretty awesome experience.

20. The Pride Parade

Known as the biggest gay neighborhood in Chicago with it’s numerous gay bars, costume shops, & rainbow flag adornments, Boystown is the perfect setting for the Pride Parade. Every summer thousands of people flock to the neighborhood to let their freak flags fly and celebrate their openly gay lifestyles. It is truly a chance to celebrate who you are and your individuality in the most accepting community in the city. There are floats and food and costumes galore! If you’re ever in the city while this is happening, I highly suggest you attend.

There you have it, folks. The definitive guide to everything you need to know about one of the greatest* cities in the world.

  • The author was born and raised in Chicago, has lived here her whole life, and might be a teensy bit biased.

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