It’s hard to pinpoint exactly why Chicago is so amazing. The city itself is beautiful to look at, even if you’re not into architecture.
The walking paths are wide and clean, making it very easy to get around. The river that snakes through the city gives it a chic European vibe. The food is world-class, and the people are friendly and welcoming.
Chicago has played an enormous part in America’s history. Culturally, politically, artistically, economically – the windy city has a pretty incredible past. It’s a city that has hosted the infamous 1893 World’s Fair, plagued by a serial killer.
A city that has built a stellar reputation on its world-class architecture, many of whom are buried there. A city that managed to reverse the flow of its river. A city that has survived fires, riots, and massacres.
There are a lot of little pockets and suburbs to get lost in, too many to see in 3 weeks, let alone 3 days. But even if you only have a few days, it’s well worth a visit.
For a short or first time trip, it’s a good idea to base yourself close to the city center. From there, you’ll have easy access to Chicago’s public transport, which is easy and cheap to use. You’ll also be able to get a good taste of the city that will leave you ready to book your return trip.
1) Start At Millennium Park
You can’t start your time in Chicago without seeing one of the city’s most popular landmarks.
Make your way to Millennium Park (Michigan Ave, bordered by Randolph St, Columbus D. and Monroe St), which is easily accessible by public transport, and see Cloud Gate (more commonly known as The Bean) up close.
If you’re game, I’d recommend getting there bright and early to beat the crowds – you know you want to get that photo without tourists in the background!
2) Head North Up Michigan Avenue Towards The Chicago River
Make a quick stop at the Nutella Café (189 Michigan Ave) to grab a Nutella waffle and hot chocolate for your walk. And if chocolate isn’t your thing, not to worry – there are plenty of other places you can stop to caffeinate for the day!
The river is another huge drawcard for the windy city, and if you’re able to visit on a sunny day, it’s easy to see why.
The river has played a huge role in Chicago’s history, with engineers actually managing to reverse the direction of its flow in the late 1800s in an effort to save the city from diseases like cholera and typhoid.
Things aren’t so grim these days, so Chicago has turned its efforts into engineering the river for more fun – like on St Patrick’s Day when they turn the water green.
Navy Pier might be a popular spot, but this might have one of the best views of the city skyline.
Named after the first African American Medal of Honor recipient, Milton Lee Olive Park sits on Lake Michigan and has the best view of the city skyline, so make sure you pack a camera.
In winter, the trees look like skeletons against the grey sky; in summer, they’re bright green against brighter blue. It can get a little chilly out on the water, so pack an extra layer of clothing, too, if you’re heading out in the colder months.
4) Visit The Chicago Sports Museum
The Bears, the Bulls, the Cubs, the White Sox, the Blackhawks… even if you’re not a sports fan, you can’t ignore the fact that this is a city obsessed with their teams.
If you’re up for a walk, it’ll take you about 20 minutes to walk to the Chicago Sports Museum (Water Tower Place, Level 7, 835 North Michigan Avenue) from Milton Lee Olive Park, and once you get there, you can see how you measure up to some of the city’s greats with some fun interactive exhibits.
5) Time For A Snack Stop At Doughnut Vault
Chicago does donuts particularly well, and Doughnut Vault (401 N Franklin St) is one of the best in the city (trust me, I’ve tried enough of them).
A teeny, tiny little hole-in-the-wall, there’s only enough space for a few people at a time to squeeze in and place their orders. They don’t have outdoor seating, either, so it’s more of a grab-and-go situation.
Get in early because they sell out fast, and grab yourself a buttermilk old fashioned. You won’t regret it.
1) Make Your Way Out To Wicker Park For The Morning
Take the blue line subway to Damen station, and spend some time exploring Wicker Park. It’s been a hipster mecca for a long time, and it just keeps getting better – think fancy boutique grocery stores, quirky artisan shops, little cafes, and all sorts of cool.
One of my favorite stops is Myopic Books (1564 N Milwaukee Ave). They have literally thousands of used books, stocked from floor to ceiling, all ready to take home with you. Get lost in the rabbit warren, but just remember, no cell phones allowed!
2) Time For Another Donut Stop, This Time At Stan’s Donuts & Coffee
Once you’re done book browsing, head a few doors down for your morning doughnut fix.
Where Doughnut Vault is small and simple, Stan’s Donuts (1560 N Damen Ave) is a cornucopia of deliciousness. Originally from Los Angeles, they’ve made their way over to Chicago and have been a great addition to the city.
Their spot in Wicker Park is a welcoming place to rest your feet, and they have an insane selection of doughnuts and cookies ready to go – I recommend the Lemon Pistachio Old Fashioned and the Coconut Cake.
3) Head For A Walk Down Michigan Ave Back Towards The City
You’ve already had a little taste with Myopic Books and Stan’s Donuts, but there are loads more fantastic shops and cafes on the way down through Wicker Park back towards the city center. You’ll also find Wicker Park itself, should you want a big, green, open space to sit and relax awhile.
If you can’t make it the whole hour it’ll take for you to walk to your lunch destination (or you can’t trust yourself not to shop your credit cards out), there are always the trains or an Uber to help you.
4) Lunch At Au Cheval
It has been declared home of the best cheeseburger in America, and people are willing to wait in line a few hours to get it. I can tell you now that the Au Cheval (800 W Randolph St) cheeseburger with egg is absolutely worth the wait.
Grab a drink at the bar in the dimly lit diner-style set up while you wait for your table. Then, order the burger and enjoy the food coma that comes after it. The fries are delicious, too. If you can, get a seat at the counter – watching the cooks at work while you’re chowing down is pretty cool!
1) Take A Hike Out Of The City And Head To Graceland Cemetery
No, a cemetery isn’t a sightseeing location you usually see on a travel itinerary, but I’m doing my best to change that. Graceland Cemetery & Arboretum (4001 N Clark St) is one of the most stunning green spaces in the city, and the resting place of some of the city’s most brilliant architects.
If you’re interested in some of the stories behind the graves, you can take a free self-guided audio tour. And if you’re not so interested in history, the grounds are beautiful enough to make it worth the visit anyway.
It’s a fair way out of the city center, though, so you may want to take an Uber.
2) Catch The Red Line Down To Lincoln Park
The scenic Lincoln Park neighborhood is enormous and has something for everyone. A nature museum, a conservatory, a harbor, a beach, a few cafes – there’s even a zoo!
Whether you want to kill half an hour or spend half the day out there, it’s a beautiful spot out on the water.
3) Next Stop Is The Chicago History Museum
Chicago is a city with a lot of history (not all of it good), and the Chicago History Museum (1601 N Clark St) presents the city’s story in the best way possible. The exhibitions are larger than life and great for kids as well as adults.
They draw you in in a way that makes them impossible to ignore – this isn’t your standard boring school field trip museum. It also has a surprisingly good gift shop with some unique souvenirs to take home with you – my favorite was the umbrella I bought with the subway map printed on it.
4) Enjoy A Bit Of Market Atmosphere At The Chicago French Market
In a city that has residents from all corners of the globe, the French Market (131 N Clinton, between Washington and Randolph) is a collection of some of the city’s best international food.
Vietnamese, Cajun, Italian, Japanese…take your pick, grab a seat in the communal seating area, and enjoy a really good feed and the market atmosphere on your last day in Chicago!
Chicago 3 Day Itinerary Wrap Up
3 days might not be enough to see all of Chicago, but by following this itinerary you will be able to see many of the local highlights!
If you are looking for more recommendations on things to do during your trip to Chicago, be sure to check out our Ultimate Guide to Chicago. Have fun in the Windy City!
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