Chicago is iconic. The third largest US city is found in Cook County, Illinois and had a population of about 2.7 million people.
Its suburbs are also affectionately known as Chicagoland and house about 9.5 million people.
Runner up in size only to New York City and Los Angeles, it’s no wonder people flock to the city every year to visit.
But where should you start when planning a trip to Chicago?
Let’s take a look at some of the must-see attractions in the city that’ll take you not only to the popular tourist spots, but off the beaten track a little too.
Monuments and Sight-Seeing
First up, it’s the big guns – the monuments and things to see around Chicago’s metropolitan area.
Booking.comThese places are guaranteed to give you the best views and sights of the Windy City – the ones that everyone talks about.
1. Willis Tower
Willis Tower (formerly called the Sears Tower) is 108 stories high. What’s amazing about this skyscraper is that it overlooks four US states.
On a clear day, you might be able to see Michigan, Wisconsin, and Indiana. Up until 1998, it was also the tallest building in the world.
It’s now second in the rankings of US tallest buildings, coming in behind One World Trade Center, which is 1451 feet taller.
Tourists love to go up to the tower’s glass observation deck, Skydeck. In fact, over 1.7 million people visit the dizzy heights each year.
Set on the 103rd floor of the scraper, the Skydeck is higher than 360 Chicago by 9 floors.
For most visitors, the highlight is the tower’s Ledge. The glass platform extends over 4 feet beyond the edge of the building. If you don’t like heights, don’t look down!
2. Cloud Gate
Another iconic Chicago spot to visit is Cloud Gate. A sculpture created by Anish Kapoor, an Indian-born British Artist.
Nicknamed “The Bean,” it was created between 2004 and 2006.
The highly polished stainless-steel plates are welded together seamlessly, making it resemble liquid mercury, as Kapoor intended (or a smoother version of the spaceship from Flight of the Navigator if you think like me!).
You can even walk under the sculpture’s archway and underneath it is the “omphalos,” which is Greek for belly button. This concave chamber warps and reproduces many reflections.
If you’re into creative photography and quirky selfies, this is definitely a place for a stop-off in your Chicago city visit.
3. Millennium Park Crown Fountain
More like an art exhibit than a typical fountain, Crowd Fountain was designed by Jaume Plensa, a Spanish Artist.
It consists of two glass towers that are 50 feet high with a shallow pool between where the water reflects images on the towers.
The photos projected are of Chicago citizens in all their glorious shapes, sizes, and colors.
Water flows from the mouths of the images, poking fun at traditional fountains.
The water flows only in the warmer months, but the images are there all year round.
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4. Chicago Observation Deck
Sitting on the 94th Floor, 1000 feet above downtown Chicago, 360 Chicago offers some of the best views of the city.
From the shores of Lake Michigan to the North, the cityscape to the West, the skyscrapers to the South and the shoreline and Navy Pier to the East, 360 Chicago really does give you unrivaled views.
But that’s not all.
360 Chicago’s TILT is a thrill-seeker’s delight. One of the highest thrill rides in the world sits atop this tower, giving riders a downwards view from 1,030 feet in the air.
You’ll be standing in an enclosed, steel and glass moveable platform that will slowly tilt you toward the floor, looking down over the Magnificent Mile.
Looking for affordable place to stay in Chicago? Check out the newest deals on booking.com
Eating and Drinking
From Chicago-style pizza, hotdogs, donuts and speakeasy drinking, Chicago has a great gastronomical offer and food festivals.
The problem is often… where do you start?
5. Visit Chinatown
The first stop on our gastronomical Chicago tour is Chinatown.
This ethnic enclave is one of the largest Chinese American concentrations in the whole of the US.
And that’s why Chicago’s Chinatown leaves you spoiled for choice when it comes to food.
Here are our top Chicago Chinatown spots:
- MingHin Cuisine – a Michelin Bib-Gourmand status restaurant.
- Ken Kee Restaurant – delicious salt & pepper pork dishes.
- Go 4 Food – great for seafood.
- Qing Xiang Yuan Dumplings – not just dumplings!
- Chiu Quon Bakery – for delicious Chinese sweet treats.
- Rebar – for Japanese eats.
6. Eleven City Diner
A casual restaurant that’s a great family choice, it comes highly rated by its patrons.
The diner hopes to rekindle the true friendly diner feel with delicious offerings coupled with nostalgia.
It’s well worth a pitstop. Or two.
7. Dinkel’s Bakery
If you’re in Chicago and you fancy a donut or cookie, look no further than Dinkel’s.
It opened over 100 years ago and is still going strong – surely that has to tell you something about their delicious offerings!
Whether you’re wanting a Danish, coffee cake or donut, the bakery has a huge selection of tasty treats to suit everyone’s taste.
8. Chicago Style Pizza
It would be remiss to write about Chicago and food without mentioning the Chicago style pizza.
Something in between a mix of an open pie and a pizza, the dish was created in 1943 and has hit the world by storm.
Here are a few places where you’ll find some of the best Chicago style pizza in the city:
- Giordano’s – with over 9,500 TripAdvisor recommendations, it’s rated at 4.5 stars! It’s a family friendly setting with delicious food.
- Lou Malnati’s Pizzeria – another popular choice for Chicago style pizza.
- Chicago Pizza & Oven Grinder – another highly rated and popular choice known for its pizza pot pie and Over Grinder sandwiches.
9. Chicago Style Hot Dogs
For a Chicago style hotdog with all the toppings, head to one of these fab little places:
- Portillo’s Hotdogs
- Devil Dawgs
- Superdawg Drive-in
10. Drink at a speakeasy
If you’re wanting to delve into the secrecy of Chicago’s prohibition past, why not sneak into a speakeasy?
You’ll find old-school entertainment coupled with classy cocktails.
- The Milk Room – a tiny microbar with expensive cocktails and just eight seats. But a visit really is a must.
- The Drifter – a venue with live entertainment and a craft cocktail bar. Quirky ordering from tarot cards adds a touch of the individual too.
- The Violet Hour – the clue it’s there is just by the long line outside an abstractly designed building frontage. For private and cozy seating areas where you won’t be disturbed, this is the place to be.
History and Culture
For most of us, visiting a new city means taking in some of the history and culture.
In Chicago, it’s easy to do just that with these fantastic places to visit.
11. Chicago History Museum
The Chicago History Museum showcases the history of the Windy City dating back to 1856. It’s an important place housing artworks, artefacts, and manuscripts. Get the tickets here.
12. Art Institute of Chicago
Founded in 1879, Chicago’s Art Institute is one of the largest (and oldest!) art museums in the world.
If art is your thing, head here to while away the hours surrounded by stunning pieces and exhibitions.
There are over 30 paintings by Monet, Pablo Picasso’s Old Guitarist and Bathers by a River by Henri Matisse. It’s a must for art lovers.
13. Museum of Science and Industry
A great time will be spent here, with more than 2,000 exhibits across 75 exhibition halls.
Some of the famous exhibits include a U-505 – a German submarine that was used in World War II.
14. The Field Museum
Chicago’s Natural History Museum delights its visitors with over 65,000 exhibits and is one of the largest in the world.
From the history of the planet to the cultural exhibitions of Tibet and China, the Field Museum covers almost every aspect of the world’s natural history. If you’re planning to visit this amazing museum, book your tickets in advance here.
Oh, not forgetting Sue, the largest T. rex skeleton found at the time which is estimated to be 67 million years old!
15. Ernest Hemingway’s Birthplace
If you’re into your literature, Ernest Hemingway Birthplace Museum is nestled in Oak Park, just to the west of downtown Chicago.
Here, Hemingway was born in July 1899 in one of the second-floor bedrooms.
Entertainment and Pleasure
Are you ready to treat yourself and your famiily with one of these cool places?
Let’s take a closer look…
16. Navy Pier
If you’re looking for a place that is full of fun for all the family, Navy Pier is worth a stop.
The pier is 3,300 feet long and sits atop Lake Michigan in the Streeterville Neighborhood.
The pier boasts 50 acres filled with gardens, parks, restaurants, shops, exhibition spaces and family attractions. Over nine million people visit the pier every year!
Within the pier, there is the Chicago Children’s Museum, the Shakespeare Theatre, and a new Ferris Wheel.
There’s also an IMAX cinema, Chicago’s Funhouse Maze, Crystal Gardens, and a new carousel. Visitors can spend the day here enjoying the entertainment and rides.
17. See the Blue Man Group
For an evening’s entertainment, you’ll never forget, enjoy a show by the Blue Man Group.
The show is oddball outrageous and a true crowd-pleaser. It’s hard to explain just exactly what makes it so amazing, but it’s definitely not something you want to miss.
Relaxing and Strolling
If you’ve been busy exploring all day, you might want to find a place to stop and relax for a bit.
Here are a few suggestions that will take your breath away as you stroll.
18. Oak Street Beach
Yes, a beach. In Chicago!
The beach lies along the shore of Lake Michigan and is one of a few beaches in the city.
19. Oz Park
Follow the Yellow Brick Road to the Windy City!
This quirky corner of the Lincoln Park Community is a delight if you’re a fan of The Wizard of Oz.
There’s Dorothy’s Playground, basketball courts, and the Emerald Garden full of flowers among many other things to see and admire.
20. Riverboat
An excellent way of taking the weight off your feet yet still seeing the sights is by riverboat.
There are many river boat tours on offer in Chicago. The Chicago River Boat Architecture tours are a pretty good choice. You can book one here.
21. The Magnificent Mile
If you are looking for a shopping district, the Magnificent Mile is the largest in the city with a variety of mid- and high-end shops to peruse.
There are also plenty of restaurants, hotels, and museums in this area too.
To give you a feel for the area, the commercial rents on the Mag Mile (as it’s affectionately known) come in third place after Fifth Avenue in New York and Rodeo Drive in Beverly Hills!
Final Thoughts on 21 Things to Do in Chicago
Whether it’s boutique stores on the Magnificent Mile, thrill-seeking in the Chicago skyline or following the Yellow Brick Road to Oz with a sneaky drink at a speakeasy on the way home, we’re sure you’ll find something in our list that makes you want to get on that plane to the Windy City right away! Now, where’s my passport?
