Your Quintessential Chicago Weekend Guide

A list of VERY cool things to do….for your Chicago weekend.

chicago bean

Chicago is known for its world-class museums, beautiful beaches on Lake Michigan, and overall friendly atmosphere. Even though it’s one of the biggest cities in the United States, it still has a small, intimate feel to it. With the endless amount of options of things you can do here, it might be hard to pinpoint what exactly you should check out if you’re only visiting for a weekend. Here are six quintessential experiences everyone who visits Chicago must do if they want to get the most out of this amazing city.

1. Take a Picture with The Bean

Millennium Park, 201 E Randolph St, Chicago, IL 60602 (map, website)
cloud gate chicago
PHOTO Mackenzie Diamond

If you’re only going to do one touristy thing while in Chicago, this better be it. Cloud Gate, more commonly known as The Bean, is considered to be one of the greatest pieces of public art in the WORLD. Even though it’s made up of 168 stainless steel plates, it has no visible seams, and its extremely polished exterior reflects the beautiful skyline. The reflective properties also make it great for photo-ops, and if you walk underneath it you’ll see how the surface warps and multiplies your reflection.

2. Visit Wrigley Field

1060 W Addison St, Chicago, IL 60613 (map, website)
Wrigley field
PHOTO Mackenzie Diamond

Baseball fans will want to check out the iconic Wrigley Field located in the Wrigleyville district of Chicago. Famous for its outfield walls covered in beautiful ivy, and the red marquee over the main entrance, it’s one of the last two “old-school” ballparks in Major League Baseball (the other being Fenway Park in Boston). It still uses a hand-operated scoreboard, and if you see a “W” flag flown from the scoreboard flagpole, you know the Cubs have been graced with a win the game before. If you can’t get tickets to the game, make sure to hit up one of the many bars by the field to cheer on the team with the locals.

3. Take a Trip Up to the Skydeck of The Willis Tower

233 S Wacker Dr, Chicago, IL 60606 (map, website)


If you’re afraid of heights this might not be for you as The Willis Tower (also known as the Sears Tower) is the tallest building in the Western Hemisphere. The skydeck is 1,353 feet in the air, with a glass box (called The Ledge) extending outwards so it feels like you’re walking on nothing but air. It’s certainly an insta-worthy visit if you’ve got the guts.

4. Admire the Art at The Art Institute of Chicago

111 S Michigan Ave, Chicago, IL 60603 (map, website)
art institute chicago
PHOTO Mackenzie Diamond

Probably most famous for being in Ferris Bueller’s Day Off, The Art Institute of Chicago is actually one of the oldest and largest art museums in the United States. It has a fantastic Impressionism gallery full of Monet, Van Gogh, Degas and more. There’s also an abundance of traditional European painting and sculpture if that’s more your style, along with photography, textiles and drawings. If you’re a lover of art this is a definite must-do.

5. Take a Stroll Along the Riverwalk at Night

Chicago Riverwalk, Chicago, IL 60601 (map, website)
riverwalk chicago
PHOTO Mackenzie Diamond

One of the best ways to admire the Chicago scenery and skyline is to walk the Riverwalk at sunset or nighttime. This nine block, pedestrian walkway contains riverside restaurants, boat rentals, and other fun activities with the backdrop of the city reflected in the waters of the Chicago River. At night the city looks breathtaking all lit up and glowing, and makes for a romantic stroll whether by yourself, with friends or your significant other.

6. Devour a Chicago Dog or Deep Dish Pizza


You’re bound to get hungry walking all around the city and what better way to curb your appetite than with a traditional Chicago dog or slice of deep dish pizza? A Chicago dog is typically topped with yellow mustard, chopped white onions, relish, a dill pickle spear, tomato slices, pickled sport peppers and a dash of celery salt. They never, NEVER put ketchup on a hotdog so unless you want to look like an obvious outsider, refrain from the condiment. If those toppings don’t sound good to you, you can always dig into some famous deep dish pizza. Don’t be alarmed when you don’t see cheese on the top, they usually put the sauce over the cheese so it doesn’t burn, since the pizza takes a very long time to bake. Expect to wait at least an hour for this glorious pizza pie to arrive, though it’s definitely worth the wait.

BONUS: Check out the Chicago Athletic Association Hotel

12 Michigan Avenue, Chicago, IL 60603 (map, website)
Chicago Athletic Association

If you want to take a quick break from the hustle and bustle of the city, step into the Chicago Athletic Association Hotel. What used to be a private athletic club back around the time of the Chicago World Fair, has now turned into a beautiful and swanky hotel. On the second floor they have a restaurant/bar in what used to be the game room of the club. You can enjoy indoor bocce courts, pool tables and chess while sipping on a refreshing cocktail. There’s also a ornately decorated lounge area that looks like it sprang right out of Hogwarts. It’s a great place to relax and enjoy a cup of coffee or tea, or read in front of one of the large fireplaces. If you’re there in the evening, check out their famous rooftop bar that overlooks Millennium Park and the lake.

Mackenzie Diamond

Business Associate

Mackenzie is a Connecticut native who loves finding the next big adventure. She enjoys cooking, dogs, and relaxing on a beach with a great book. If you want her heart, you find it on top of the Duomo in Florence.

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