Chicago, the windy city. Once called the Second City, Chicago is now the third-largest city in the US after New York and Los Angeles. Sitting on the southwest shore of Lake Michigan, in the State of Illinois, Chicago is known for Al Capone, The Blues Brothers, being the starting point of Route 66, and great sports teams like the Bulls, Bears, and Blackhawks. The city likes its B’s. With plenty of things to do in Chicago, here are my favourites.
1) Take a Walk in Millennium Park
With 24 public beaches, numerous parks, and plenty of attractions along Chicago’s 26-mile waterfront, you could spend all your time exploring that area alone. At 25 acres, Millennium Park is a huge green space that contains concert areas, manicured gardens, rock climbing, sculptures, and the famous Buckingham Fountain, featured in the opening credits of the TV sitcom, Married With Children.
Between my wife and I, we’ve been to Chicago a half dozen times, taking in different sites each visit. We’ve found a huge variety of things to do in Chicago. On our last trip, we entered the park via the Cloud Gate, across Lakeshore Drive and the official starting point of the famous Route 66. There are bicycles to rent if you don’t think you can take in all the sites on foot. The Cloud Gate, better known as Chicago’s Bean, is a mirrored kidney bean-shaped piece of unique art.
Near The Bean is the Crown Fountain, a black granite reflecting pool, situated between two glass brick towers that overlook the water feature and come to life with larger-than-life video images. Its ever-changing artistic displays complement the nearby Art Institute. Millennium Park sits between Lake Michigan and Lakeshore Drive, which skirts the great lake along the city’s eastern border.
2) Moor Yourselves at Navy Pier, One of the Best Things to Do in Chicago
About two miles north of Millennium Park is Navy Pier — a bit of a walk for most but easily reachable by bike, bus, or car. Off Lakeshore Drive, the entrance to the 3,300-foot pier is surrounded by more parkland and greenspace. Extending into Lake Michigan, Navy Pier offers things the whole family can enjoy. Besides restaurants like Harry Caray’s Tavern and Margaritaville, there is a giant Ferris wheel, various rides, and a funhouse.
There is an observation deck at the end of the pier and various lake and river cruises, with the latter taking you into the city, along the Chicago River. The Billy Goat Tavern, a Chicago burger institution made famous on Saturday Night Live (think cheezborger, cheezborger, cheeps — no fries). Note: this is a franchise, the original location is downtown, off West Madison Avenue. Go there for the real deal.
3) Stroll Along Chicago Riverwalk
From Navy Pier, follow the Lakefront Trail that goes under Lakeshore Drive and connects with the Chicago Riverwalk. Whereas there is a River Esplanade on the north side of the Chicago River, the Riverwalk follows the waterway’s southern edge. The scenic pathway, with towering skyscrapers on both sides, is below street level and takes you under an assortment of new and cool old city bridges.
You can easily spend a whole day walking or cruising along the Riverwalk if you’re looking for things to do in Chicago. There are cruises from Navy Pier and water taxis that pick up and drop off at different stations along the waterway. As well as a concert area, there are several picnic spots, public washrooms, cafes, restaurants, brewpubs, and even a winery to check out. The Riverwalk dissects downtown, where countless stores and eateries can be reached by taking the stairs up to street level.
The Chicago River is the only river in the world that flows in the wrong direction — a man-made feature to bring fresh lake water into the city. Due to the clay bottom, the water is a lovely blue-green color. It’s also dyed green for St. Patrick’s Day every year. The Riverwalk offers great views of buildings like the Willis Tower (former Sears Tower — once the tallest in the US) with its glass sky deck and Marina City.
4) Watch Sports
Sports fans will love Chicago for its professional sports teams. Hockey has the Blackhawks, basketball the Bulls, football the Bears, and there are two teams for baseball — the White Sox of the American League and Cubs of the National League. The Cubs’ Wrigley Field is a national historic landmark and one of the last remaining century-old open-air ballparks. If you’re looking for things to do in Chicago, don’t miss this one.
5) Go Downtown
It’s been said that Chicago is one of the most easily walkable big cities in the US. However, if your feet can’t handle the action, jump on the L, Chicago’s historic elevated mass transit system that crisscrosses the city, running on steel stilts above city streets. Each time we’ve visited Chicago we stayed downtown for ease of access to the L for major sites and things to do.
On our last visit, we chose the historic Congress Plaza Hotel on Michigan Avenue. Opened in 1893 as a world-class hotel, this place catered to famous folks from around the globe. While waiting to check in, a friendly hotel security guard took us on a tour. He showed us the beautiful grand ballroom and a secret outer room where Al Capone played cards.
Just around the corner, we found one of the notorious gangster’s watering holes, the Exchequer Restaurant & Pub, on South Wabash. It’s a four-minute walk from the Art Institute of Chicago. The Magnificent Mile, a high-end shopping area, runs along Michigan Avenue, north of the river. If you visit the city in summer there are numerous music events, like Blues and Jazz festivals, held in Millennium Park. We took in the Jazz Fest on a previous visit. On our last trip, we dined at Andy’s Jazz Club & Restaurant. The meal was delicious and at one point our waiter excused himself to take the stage and sing.
6) Explore Chicago’s Major Attractions
If the weather is sketchy and you’re in need of indoor activities there is the Shedd Aquarium, Lincoln Park Zoo, Chicago Children’s Museum, and Field Museum. There’s the Chicago Theatre and Lyric Opera, or pamper yourself at the AIRE Ancient Baths. Even Chicago’s historic Union Station — the film location for countless movies — is something to see.
7) Dine Out in Chicago
Eating and trying regional specialties is one of our favorite things to do when Cathryn and I travel. Chicago offers traditional American cuisine but there are neighborhoods like Greektown and Chinatown that offer their own fare. Some folks rave about Chicago-style pizza, but we prefer our own Italian-influenced pie from home, in Windsor. You definitely have to try the burgers and experience the ambience at the original Billy Goat Tavern.
Navy Pier’s home to the Chicago Children’s Museum. Within that attraction, you’ll find Harry Caray’s Tavern. This is a family-friendly eatery serving American classics with plant-based options for visiting vegans. Head to Rush Street in the Gold Coast neighborhood at weekends where restaurants add al fresco seating thanks to the streets being blocked off to traffic.
Our last trip to the Windy City was for our journey along the historic Route 66, with its official starting point in downtown Chicago at the edge of Lake Michigan. To set the mood for our cross-country journey to Santa Monica, we had breakfast at Lou Mitchell’s Restaurant & Bakery, circa 1923, where they give out donut holes and Milk Duds after your meal.
Celebrities from around the world have dined at Lou’s and it’s still a favorite for many locals. During our visit, I got to ogle members of the Chicago Police intelligence unit, decked out in their crested and matching black golf shirts. The team has been immortalized by the television show, Chicago P.D.
I hope this article gives you a taste of what to expect on a visit to Chicago. If you liked reading it, I’m sure you will enjoy my site too. Why not drop by Life Written and Reviewed for a while?
53 Comments. Leave new
Wow, that Buckingham Fountain looks amazing 🤩 Great recommendations! Thanks for sharing, we’ll definitely use this as a guide on our trip to Chicago next year.
Thank you, Irena. It’s a great city and I’m sure you’ll enjoy your visit.
I’ve only visited Chicago once when I was over visiting the US a few years back. 2015 I believe. Lovely city but we didn’t have a lot of time to do much as we were on a schedule. Definitely on the list to revisit.
I agree, Nyxie, we find new things to see and do every time we visit.
If you take one activity from each section in this article, you’d have a very full weekend! (Might have to extend it to a 3 or 4 day weekend.) Any two activities would make for a complete day-trip. Thanks!
You’re right, Scott, it’s easy to fill a weekend in the Windy City. We continue to discover new things to see and do every time we visit.
I have never been to Chicago before. I have wanted to go, so I will keep your ideas in mind!
Put it on your bucket list, Amber.
So many great ideas! I’m at senior at Notre Dame, and somehow, the only times I’ve been to Chicago have been flying into and leaving the airport! I’ll definitely have to do some of these things before I graduate!
If you ever have a long layover, Malia, hop in an Uber or taxi and check it out.
Ive always wanted to visit Chicago and stroll along the river. Also, I didnt realize how many things we can do in this place.
The Riverwalk is really cool, Beth, I hope you get there.
There are so many things to do in Chicago. We live close by but I have never been here. I wanted to try their Deep Dish Pizza
It’s about 5 hours for us, Brianne, so if you’re as close you really need to check it out.
So much to see and do, I can’t wait to visit Chicago.
I hope you get there, Tasheena.
My daughter lives there and we’ve done all of these! You have hit some great spots.
That’s good to hear, Terri, great minds think alike 🙂
Great list! Heading to Chicago is always on my bucket list and now I know some places that I need to go see!
Sounds like it’s about time to reach into that bucket, Thena. Happy travels!
I love the museums and exhibits in Chicago. You cant miss them when you visit Chicago
My wife and I aren’t big museum buffs, but do like to visit when the weather outside is inclement.
I have a cousin who lives in Chicago who’s constantly complaining about the cold, and feeling lonely (recently moved there). I will forward your post to him.
It gets plenty cold here in Canada too, but it’s only that way for a few months in Chicago. They have great summers.
Chicago has so much to offer, great experiences all. The Navy Pier Is where we would like to be,
There is lots to offer, we spent half a day on Navy Pier my first visit. Cheers!
Chicago is one of my favorite cities to visit. There are quite a few restaurants I would like to go back to again.
Too many restaurants and not enough time to try them all, but we have favorites that always steal our attention.
I’ve been to Chicago a few times before. It’s such a beautiful city too. They sure do have a lot to do and look at.
I agree, Kathy, thank you for your feedback.
I really wanted to go and visit Chicago, the restaurants there are really awesome specially the foods!
I hope it’s on your bucket list, Richelle. Cheers!
I’ve never been to Chicago but I’m hoping to visit in the next year. Looks like a great city!
I hope you get there, Jenn, you won’t be disappointed.
I have visited the US but never been to Chicago before. It’s good to hear about this city. I’d love to go to Millennium Park.
I hope you get there some day, Melanie, you can get lost in the size of that park.
Great article. Chicago is always my favorite city. Wanna vist this with my friends so soon
Thank you, Abida. Hope you and your friends get there soon.
One of my favorite cities is Chicago and I have visited all these places. Great post!
Thank you for your feedback, Kushigalu.
I still haven’t been to Chicago, but it sounds like a great place to explore, with plenty to see and do!
Hopefully, Marysa, you’ll put it on your bucket list.
Nice article Ed. It’s interesting you should mention the river’s flow. The Tonle Sap in Cambodia has a unique phenomenon in where it changes direction twice a year.
The Tonle Sap River flows from Tonle Sap lake into the Mekong for half of the year and then reverses and flows away from the Mekong. If I am not mistaken, this is the only river in the world which does this.
I didn’t know that. The Reversing Falls in St. John New Brunswick is similar but flows with the tides.
Chicago’s was manmade to reduce sewage problems.
I would absolutely love to go to Chicago one day and get to explore a bit! These sound like absolutely wonderful things to check out when there too.
Thanks for your feedback, Sarah, I hope you get there.
A great place to explore, Sarah, I hope you get there soon!
This is great! Hope to visit Chicago one day! Looks so lovely
I hope you go too, Samantha, you won’t be disappointed.
Put it on your bucket list, Samantha. Bon Voyage!
I am definitely taking a walk on the Riverwalk and park! That’s just my favourite sceneries! Thanks for sharing about them.
You’re welcome, Ntensibe, thanks for your feedback.
I spend my 40th birthday in Chicago and I fell in love with the city. Pity you didn’t write this piece before I went there because I missed Lou’s restaurant 🙁 Great photo gallery !