Chicago Bucket List
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Take an Architecture River Cruise
Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is also a fun activity. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. Summer is the best season for a lake cruise as the cool breeze on the water is refreshing on a hot day. If your time is short, you can do a combination river and lake cruise.
Hang Out on the Riverwalk
The Chicago Riverwalk is a pedestrial walkway along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. It is one of the best spots in Chicago for boat and people watching especially in the summer.
If you are on the Riverwalk at night, check out Art on theMART, a 30-minute program of digital art projections shown twice nightly across the river-façade of the Merchandise Mart. Spectators can watch the show from the jetty section of the Riverwalk on Wacker Drive between Wells Street and Franklin Street.
Go Kayaking in the River
Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Ride the Large Ferris Wheel at Navy Pier
Navy Pier is a not to missed attraction especially if you are visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), rides and games, restaurants, shops and the Chicago Children’s Museum. Visiting Navy Pier is free, although you have to pay for the attractions.
Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises.
Watch Free Fireworks at Night
As mentioned above, Navy Pier puts on a fireworks show every Wednesday night and Saturday night from Memorial Day weekend through Labor Day weekend. While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars.
Another great option for watching the fireworks is a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.
Stand on the Ledge at Willis Tower
The Willis Tower (formerly known as the Sears Tower and what many locals still call it) used to be the tallest building in the world from 1974 until 1998. You can enjoy great views from The Skydeck, its observatory on the 103rd floor of the Willis Tower (233 S Wacker Dr). For the best instagram photos head to The Ledge, glass balconies extending four feet outside the 103rd floor.
Tip: The Skydeck Chicago gets crowded especially on weekends. For fewer crowds visit right after it opens during midweek. (Click here to buy a skip the line ticket if you want to avoid long lines).
Enjoy Skyline Views from 360 CHICAGO Observation Deck
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360 CHICAGO (formerly John Hancock Observatory) on the 94th floor of the 875 North Michigan Avenue (the building formerly known as the John Hancock Center) is another observatory with great Chicago skyline views. It gets crowded especially on weekends (but is usually less crowded than the Skydeck). (Click here to buy a skip the line ticket).
The highlight is TILT an enclosed moving platform that tilts you out over Michigan Avenue. You can also experience TILT, an enclosed moving platform that tilts you outward over Michigan Avenue for unique, downward facing views.
See Cloud Gate (The Bean)
If you have seen photos of Chicago, chances are you have seen photos of Cloud Gate (which most people call The Bean), the iconic mirrored sculpture in Millennium Park. The Bean is a must see attraction is one of the top photo spots in Chicago.
Listen to Free Music in Millennium Park
A great Chicago activity in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.
The annual Grant Park Music Festival is the only free outdoor classical-music concert series in the US. It features the Grant Park Symphony Orchestra and Grant Park Chorus along with guest performers and conductors.
The Millennium Park Summer Music Series features a wide variety of genre-defying music from established and emerging artists.
Watch the Water Displays at Buckingham Fountain
Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world.
When the water is turned on (usually May to October), it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display.
Shop (or Window Shop) on the Magnificent Mile
Join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the 360 Observation Deck, the historic Chicago Water Tower and the Tribune Tower.
Visit the Art Institute of Chicago
Chicago has many great museums which are worth visiting. The Art Institute of Chicago, conveniently located right next to Millennium Park, is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. In addition to its large permanent collection of art from around the world, you can see rotating exhibits. (Click here to buy a skip the line ticket if you want to avoid long lines).
Visit the Museum Campus
Other must see museums in Chicago include the Adler Planetarium, the Shedd Aquarium, and The The Field Museum. They are all located near each other on The Museum Campus. (The Adler Planetarium is temporarily closed but it is worth visiting the Adler Planetarium Skyline Walk for one of the best skyline views in Chicago.)
Visit the Museum of Science and Industry
The Museum of Science and Industry in Hyde Park is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits.
Promontory Point is about a half mile away and has great skyline views of Chicago.
Explore the Lakefront Trail
Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. In the summer and especially on weekends, the lakefront is packed with locals and visitors walking, running and riding bikes. Walking or biking all or part of the trail is a great way to see Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.
Visit North Avenue Beach
Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan. Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions.
North Avenue Beach is a busy and popular beach and is located close to Lincoln Park. Even if you are not a beach lover, North Avenue Beach is worth visiting just for the amazing skyline views.
Enjoy the Views from a Rooftop Restaurant
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Chicago has several rooftop bars and restaurants with amazing views of Chicago. These rooftops have bucket list worthy views:
LH ON 22 (85 East Wacker Drive) offers great views of the Chicago River.
Cindy’s (12 S Michigan Ave), a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel, offers panoramic worthy views of Millennium Park and Lake Michigan.
The J. Parker (1816 N Clark St) on the rooftop of the Hotel Lincoln, has great views of Lincoln Park.
Watch a Baseball Game at Wrigley Field
Whether a fan of the Cubs, baseball in general or just a lively atmosphere, a day at historic Wrigley Field is a must for locals and tourists alike. You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating.
You can find the Cubs’ schedule here.
If you cannot find tickets, you can watch a game from Wrigley View Rooftop.
You can also sign up for tours of the stadium for a behind-the-scenes look.
See a Show at the Chicago Theatre
The Chicago Theatre, located on State Street in the Loop, is a recognizable landmark because of its iconic Chicago sign. You can see a show here or pass by and snap of photo for instagram.
Walk The 606
The 606 is Chicago’s version of The Highline in NYC, an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. It is a bit off the beaten tourist path but it great place to walk, run or bike. There are several access points so you can get off the trail to explore the various neighborhoods.
Have a Chicago-Style Hot Dog
Try a Chicago-style hot dog – one of foods that Chicago is most famous for. The classic version of the Chicago dog is an all-beef hot dog served on a poppy seed bun and topped with yellow mustard, pickle, relish, sliced tomato, onions, sport peppers and celery salt. Ketchup is not allowed. You can find hot dog stands all over Chicago Portillos is a popular spot and convenient as it has outposts all over Chicago.
If you are not visiting Chicago soon, you can order Chicago style hot dogs online here and enjoy them from home.
Try Deep Dish Pizza
Chicago is famous for Chicago-style deep-dish pizza. The main difference between deep-dish pizza and most other forms of pizza is that the crust is very deep, creating a very thick pizza that resembles a pie more than a flatbread.
There is a lot of debate which restaurant in Chicago serves the best deep dish pizza but you can’t go wrong with either Lou Malnati’s or Giordano’s, two of the most popular pizza places with several locations in downtown Chicago. If you do eat at one of these keep in mind that they are usually busy especially on weekends and in the summer (during peak times you will often see people waiting outside on the sidewalk).
Most locals prefer Pequods in the Lincoln Park neighborhood of Chicago which is said to have the best deep dish pizza in Chicago and is famous for its caramelized crust.
Try an Italian Beef Sandwich
Although not as well known as deep dish pizza and Chicago style hot dogs, Italian beef is another dish Chicago is famous for. Al’s Italian Beef is the best and most famous place in Chicago to try an Italian beef sandwich. Another good spot is Portillos if you are there for a Chicago hot dog.
These things are the top things to do, see and eat in Chicago that need to be on your bucket list.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
Need more bucket list inspiration? You might enjoy our other travel bucket lists:
- Best Places to Visit in the Midwest for Your Bucket List
- USA Travel Bucket List: 100+ Best Places to Visit in the United States
- Best Road Trips in the USA For Your Bucket List