Considered one of the great cities of the United States and World. Chicago has no limit to the amount of wonderful things to see, do, and eat in this great city. We help you plan your trip through Chi-town, and explore some of it’s best things to do. Follow along. If you have any other suggestions or recommendations, we’d love to hear them too.
Shop and Walk the Magnificent Mile
The premier shopping area of Chicago, the Magnificent Mile has many of the high-end retail and food options in the city. Sometimes I don’t think it’s quite as premier as it once was with things moving to other areas of the city as well. But its still worth wandering and checking out while you are in the city. It does have a grandeur feeling in places. The magnificent mile extends along Michigan Avenue from Oak Street to the Chicago river.
Wander the Riverwalk
The Riverwalk takes folks along the south bank of the Chicago River near Wacker Drive. The Riverwalk has great restaurants, bars, art installations, shops, as well as great views of the architecture along the water as well. On a beautiful day it’s the perfect place to walk, grab a bite, and/or people watch.
Get Out on the Water
There’s multiple options for getting out on the Chicago River. For those who want to burn calories, you can rent a kayak at various spots along the river. For everyone else, getting on a boat tour of the river is a great way to see Chicago. There are quite a few outfits that do boat tours on the river. Some about Chicago History, Architecture, or just fun nights, food, and drink on the water. Whatever your preference, there’s certainly an option for you. Urban Kayaks is a great choice for those looking for kayaks.
Enjoy the Extensive Cuisine of Chicago
Sure you can get Chicago hotdogs and pizza, but what really brings Chicago alive for me is the extensive ethnic cuisine of all of its inhabitants. From amazing Pakistani Kabobs, Japanese Sushi, Ukrainian dumplings, Moroccan Tagine, there’s something from nearly everywhere in Chicago. Food is what brings me back to the city time and time again. And it’s people are what really make the city what it is.
Willis Tower Observation Deck
I still think of the Willis Tower as the Sears Tower. But it’s definitely a more interesting observation deck than existed back in those days as well. It gives you a great view of the city and the skyline from the Observation Deck of the Tower. You will be in the third tallest building in the Western Hemisphere, and stepping out onto the class may give vertigo and likely a thrill too. Open Daily.
Tickets: Skydeck Website
Address: 233 S Wacker Dr, Chicago, IL 60606
Find Adventures in Maggie Daley Park
The small 20 acre park has a lot of things to explore and do in the city of Chicago. I feel that the park has more adventure-some things than the other parks around it. There’s a climbing wall that is open to the public as well as mini golf, ice skating, tennis courts, roller skating, and more. It’s fun for all ages for sure, and I love that its got way more fun things to do than the other parks nearby. You can also sit and relax in the garden though if that’s your speed too.
Address: 337 E Randolph St, Chicago, IL 60601
360 Chicago
While not as tall as the Willis Tower’s Skydeck, you’ll likely not notice the difference from the 94th story of the John Hancock Building. The 360 Chicago Experience has a tilting glass lookout that allows you to lean and look down at the city ahead and below. You can stay up there longer if you want and you can definitely get great views all day but in particular if you go early or around sunset for great light. You have the options to do the views from the observation deck or include the “tilt” view for more thrills.
Tickets: 360 Chicago Tickets
Address: 875 N Michigan Ave 94th floor, Chicago, IL 60611
Lincoln Park
One of the loveliest neighborhoods and parks in the city, the 1208 acre park along Lake Michigan has walking trails, museums, gardens, and more to explore in the city. It really feels like a refuge away from the urban environment and being in the park feels a world away. During my times in the park it’s nice to just sit and relax either in the Lincoln Park Zoo (below) or along the benches in the park. There’s also several sports fields for those looking to enjoy various sports with friends or clubs.
Lincoln Park Zoo
This 35 acre zoo, located within Lincoln Park has animals from across the world. And the zoo is free. Although parking is rather expensive however. It’s a great place to wander around and explore. You can spend as much or as little time and it has things for all ages as well. Some areas of the zoo could definitely use a refresh, but for the price, location, it’s great to explore and enjoy, especially on a beautiful Chicago day.
Address: 2400 N Cannon Dr, Chicago, IL 60614
Price: Free; Parking: $20-35
Catch a Play or Musical
As someone who lived in New York City for years, I do have a tendency to pick on other cities theater scene. However, you can see great shows, plays, and musicals in Chicago. In particular, the Chicago Theatre is host to a lot of great acts. It’s also a wonderful landmark building and one of the most photographed in the city as well. Be sure to check the website for the Chicago Theater (as well as other theaters) for the latest and current productions.
Address: 175 N State St, Chicago, IL 60601
Website: The Chicago Theatre
Go to the Beach
There are beaches in Chicago and some of them quite large and extensive. Sitting on the shores of the lake, you really could be on some sea or ocean somewhere else. The beaches are a great place to wander, play volleyball, sunbathe, or just relax and enjoy the lovely days. It’s very seasonal though, as weather can cause the beaches to be completely empty. My most recent trip to the beach showed some empty sand, partly due to the weather (although did warm up) as well as possibly being a weekday.
Explore Chi-Town History at the Chicago History Museum
Fascinating Museum chronicling various aspects of Chicago History. With exhibits on areas such as the Chicago Fire, civil rights, fashion, culture, politics and more. There are several permanent and rotating exhibits that pass through the museum through the years so there’s often something new for you to visit as well. Reminds me some of the Museum of New York that I enjoy in that city as well.
Address: 1601 N Clark St, Chicago, IL 60614
Tickets: Chicago History Museum
Wander the Lakefront Trail
This 18.5 mile trail takes walkers, runners, and more along the western shore of Lake Michigan. I love how the trail changes from more urban feeling in areas close to downtown to more scenic and sandy as you come up or down the trail. The trail goes from Kathy Osterman Beach in in Edgewater all the way to the south end of Jackson Park.
Get some Deep Dish Pizza
Like other cities, Chicago also has it’s famous culinary creations. And none more famous than the Chicago Deep Dish Pizza. Everyone has their favorite in the city. Some swear by Lou Malnati’s and others wouldn’t go anywhere other than Giordano’s and other’s prefer a local spot in their neighborhood. All of my Chicago friends are die hard fans of their particular favorite. Regardless, while its not an every day food, and even if you’ve had it elsewhere. Trying it in it’s birthplace is a must.
Explore the Neighborhoods
There’s a lot of great neighborhoods all across Chicago. From West Loop to Lincoln Park to Ukrainian Village or Wicker Park, or Gold Coast and more. Each place in the city has is unique character, unique history, food, and charm. Wandering the neighborhoods is a great way to see the diversity of the city. To check out the lovely parks, restaurants, and more. It’s my favorite way to get to know a city. And it’s one of the best ways to explore and learn about Chicago.
Grab a Bite at One of the Many Markets
Food Halls are some of my favorite places in cities. And some of my favorite places to eat as well. Many of them also cater to local cuisines and local restaurants which is a great way to showcase and sample what a city has to offer. Chicago has quite a few throughout the city, from Time Out Market in West Fulton Market in the West Loop. Revival Market or Urbanspace downtown, as well as others throughout the city. I do like the vibe and the choices of the various markets. Fun places to meet up so each can get what they are craving.
Address: (Time Out Market) 916 W Fulton Market, Chicago, IL 60607
The Art Institute of Chicago
Founded in 1879, the Art Institute of Chicago is one of the oldest art museums in the world. The museum houses one of the largest collections of impressionist and post-impressionist paintings in the world with iconic works from Picasso, Grant Wood, Edward Hopper and more. The museum has permanent collections cataloging works from the Americas, Europe, Ancient, Asian, as well as modern works and photography. It’s definitely a great place for art lovers to get lost an explore.
Address: 111 S Michigan Ave, Chicago, IL 60603
Tickets: Art Institute of Chicago
Visit Millennium Park and the Bean
Opened in 2004 and taking up approx. 34 acres on the northern end of Grant Park; Millennium Park was created to celebrate the new millennium. The park has a lot of lovely things to see in the area, and it has quite a few attractions. From the famous cloud gate sculpture (affectionally called “the bean”), to the Jay Pritzker Pavilion bandshell, to the odd faces in the fountains area. The park also has a ice skating rink in the winter months as well. You’ll even get some cool views of the city and buildings from the park (as seen in the photo). Definitely worth exploring and enjoying and a central point for many folks in the downtown area.
Address: 201 E Randolph St, Chicago, IL 60602
Take in the Dinosaurs and Displays at the Fields Museum
One of the premier Natural History Museums in the United States if not the World. The Field’s museum has an extensive collection of natural exhibits of plants and animals. The museum has an incredible permanent collection that includes artifacts from ancient Egypt, traditional clothing, precious stones, animals, plants, as well as a really great set of dinosaur fossils, including “Sue”, the Tyrannosaurus Rex. Which is one of the best preserved and largest T-Rex specimens ever discovered.
Address: 1400 S Lake Shore Dr, Chicago, IL 60605
Tickets: The Fields Museum
Hang out with the Fishes at Shedd Aquarium
When I talked with some of my friends, their favorite of the museums is the Shedd Aquarium. Housing over 30,000 animals, the Shedd Aquarium is one of the largest aquariums of its kind in the world. The 5 million gallon aquarium open originally in 1930 and has grown to include specimens from around the world. It is actually even more popular than the Fields Museum in terms of annual visitors. You’ll find an incredibly variety of water life here including stingrays, sharks, whales, turtles and more. Also they have some great land/water exhibits such as those featuring penguins, seals, sea otters and more. Definitely a great way to spend a part or a full day.
Address: 1200 S DuSable Lake Shore Dr., Chicago, IL 60605
Tickets: Shedd Aquarium
Shoot for the Stars at Adler Planetarium
Open Daily, the Adler Planetarium incredible displays and shows that explore the universe. You can learn about the solar system, explore some of the beautiful planetary exploration vehicles, learn about planets and more. There’s an incredible amount of exhibits to view including areas of Chicago’s nigh sky, missions to the moon and beyond, as well as rovers, etc. Even if you don’t watch a show (which you should do), there’s still plenty to do at the Planetarium.
Address: 1300 S DuSable Lake Shore Dr., Chicago, IL 60605
Tickets: Adler Planetarium Website
Hang out and Ride at Navy Pier
The long pier into Lake Michigan is one of Chicago’s most famous attractions. You can’t miss the large Ferris wheel, that is probably the most recognizable attraction at the pier. The pier opened in 1916 to the public. The Ferris wheel at the pier took inspiration from the World’s First Ferris Wheel in Chicago at the World’s Columbian Exposition in 1893. The current Ferris wheel soaring over 200 feet was completed in 2016 and replaced the older Navy Pier Ferris Wheel. Access to Navy Pier and admission to the pier itself is free. However, games, rides and other attractions are an added cost. Even just wandering around the pier and taking in views of the water and city is a great stop on any visit to Chicago.
Address: 600 E Grand Ave, Chicago, IL 60611
Website: Navy Pier
Laugh at Second City
Second City is one of the most famous, if not THE most famous improv comedy place in the world. The name comes from a set of articles that mocked Chicago as “the second city”, of which they took the self-mocking name as a badge of honor. Second City has become one of the most influential comedy theaters in the country and world and alums of the theater include Alan Alda, Bill Murray, Tina Fey, Amy Poehler, Stephen Colbert, Chris Farley, and many many more. It truly is a who’s who of comedy. Several Alumnus from Second City went on to found Upright Citizen Brigade in NYC which is one of the best in NYC.
Address:1616 N Wells St. Chicago IL, 60614
Tickets: The Second City
Catch a Game
Chicago is one of the best and biggest sports cities in the country if not the world. Chicagoans are die-hard fans of their sports teams and definitely there’s some contention between a few that split some areas of the city. I used to love Chicago sports in my youth, watching the Bulls of the 90s just dominating the sport. Being able to take in a game whether it be the Bulls, Bears, or Cubs in a city that lives and breathes these teams is something worth being there for. I also like that a lot of the stadiums are still downtown unlike other cities that moved them further from the city.
Pullman National Monument
Located in South Chicago, Pullman National Monument the company town of the Pullman Company that was famous for it’s sleeper cars. The city was one the first planned industrial cities in the US, and a birthplace of unionization for African Americans as well. Years later the town was pulled into the larger city of Chicago where it is still today. Getting here is best done for those who have a car. It’s certainly worth visiting if many of these National Monument sites are of interest to you as well.
Bahai Temple
One of the largest and most beautiful temples for the Bahai Faith. It was even the first ever temple for the faith as well, planned by local believers even with input of the founder of the faith (who was imprisoned at the time). It’s quite an area of peace and tranquility and worship. The site is open to visitors for the most part, although you should be sure to not disturb those there for prayer. It’s also interesting place for learning about a religion unknown to most Americans.
Address: 100 Linden Ave, Wilmette, IL 60091
Website: Bahai Temple
Other Posts you May Like
- ILLINOIS: Exploring Pullman National Monument
Leave a Reply