{"id":47668,"date":"2020-11-18T08:00:13","date_gmt":"2020-11-18T16:00:13","guid":{"rendered":"https:\/\/wearetravelgirls.com\/?p=47668"},"modified":"2025-08-26T01:19:06","modified_gmt":"2025-08-26T08:19:06","slug":"chicago-3-day-itinerary","status":"publish","type":"post","link":"https:\/\/wearetravelgirls.com\/chicago-3-day-itinerary\/","title":{"rendered":"3 DAY ITINERARY TO CHICAGO, ILLINOIS"},"content":{"rendered":"

It\u2019s hard to pinpoint exactly why Chicago is so amazing. The city itself is beautiful to look at, even if you\u2019re not into architecture.<\/p>\n

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.<\/p>\n

Chicago has played an enormous part in America\u2019s history. Culturally, politically, artistically, economically \u2013 the windy city has a pretty incredible past. It\u2019s a city that has hosted the infamous 1893 World\u2019s Fair, plagued by a serial killer.<\/p>\n

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.<\/p>\n

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\u2019s well worth a visit.<\/p>\n

For a short or first time trip, it\u2019s a good idea to base yourself close to the city center. From there, you\u2019ll have easy access to Chicago\u2019s public transport, which is easy and cheap to use. You\u2019ll also be able to get a good taste of the city that will leave you ready to book your return trip.<\/p>\n

\"view<\/p>\n

Day One<\/h2>\n

1) Start At Millennium Park<\/h3>\n

You can\u2019t start your time in Chicago without seeing one of the city\u2019s most popular landmarks.<\/p>\n

Make your way to Millennium Park<\/a> (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.<\/p>\n

If you\u2019re game, I\u2019d recommend getting there bright and early to beat the crowds \u2013 you know you want to get that photo without tourists in the background!<\/p>\n

\"Millennium<\/p>\n

2) Head North Up Michigan Avenue Towards The Chicago River<\/h3>\n

Make a quick stop at the Nutella Caf\u00e9<\/a> (189 Michigan Ave) to grab a Nutella waffle and hot chocolate for your walk. And if chocolate isn\u2019t your thing, not to worry \u2013 there are plenty of other places you can stop to caffeinate for the day!<\/p>\n

The river is another huge drawcard for the windy city, and if you\u2019re able to visit on a sunny day, it\u2019s easy to see why.<\/p>\n

The river has played a huge role in Chicago\u2019s 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.<\/p>\n

Things aren\u2019t so grim these days, so Chicago has turned its efforts into engineering the river for more fun \u2013 like on St Patrick\u2019s Day when they turn the water green.<\/p>\n

\"View<\/p>\n

3) Head East Along The River, North Up To Navy Pier, And Then On To Milton Lee Olive Park<\/h3>\n

Navy Pier<\/a> might be a popular spot, but this might have one of the best views of the city skyline.<\/p>\n

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.<\/p>\n

In winter, the trees look like skeletons against the grey sky; in summer, they\u2019re 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\u2019re heading out in the colder months.<\/p>\n

\"Trees<\/p>\n

4) Visit The Chicago Sports Museum
\n<\/strong><\/h3>\n

The Bears, the Bulls, the Cubs, the White Sox, the Blackhawks\u2026 even if you\u2019re not a sports fan, you can\u2019t ignore the fact that this is a city obsessed with their teams.<\/p>\n

If you\u2019re up for a walk, it\u2019ll take you about 20 minutes to walk to the Chicago Sports Museum<\/a> (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\u2019s greats with some fun interactive exhibits.<\/p>\n

Related Post: <\/strong>The Ultimate Chicago City Guide<\/a><\/div>\n

5) Time For A Snack Stop At Doughnut Vault<\/h3>\n

Chicago does donuts particularly well, and Doughnut Vault<\/a> (401 N Franklin St) is one of the best in the city (trust me, I\u2019ve tried enough of them).<\/p>\n

A teeny, tiny little hole-in-the-wall, there\u2019s only enough space for a few people at a time to squeeze in and place their orders. They don\u2019t have outdoor seating, either, so it\u2019s more of a grab-and-go situation.<\/p>\n

Get in early because they sell out fast, and grab yourself a buttermilk old fashioned. You won\u2019t regret it.<\/p>\n

\"Doughnut<\/p>\n

Day Two<\/h2>\n

1) Make Your Way Out To Wicker Park For The Morning<\/h3>\n

Take the blue line subway to Damen station, and spend some time exploring Wicker Park. It\u2019s been a hipster mecca for a long time, and it just keeps getting better \u2013 think fancy boutique grocery stores, quirky artisan shops, little cafes, and all sorts of cool.<\/p>\n

One of my favorite stops is Myopic Books<\/a> (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!<\/p>\n

\"Wicker<\/p>\n

2) Time For Another Donut Stop, This Time At Stan\u2019s Donuts & Coffee<\/h3>\n

Once you\u2019re done book browsing, head a few doors down for your morning doughnut fix.<\/p>\n

Where Doughnut Vault is small and simple, Stan\u2019s Donuts<\/a> (1560 N Damen Ave) is a cornucopia of deliciousness. Originally from Los Angeles, they\u2019ve made their way over to Chicago and have been a great addition to the city.<\/p>\n

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 \u2013 I recommend the Lemon Pistachio Old Fashioned and the Coconut Cake.<\/p>\n

\"donut<\/p>\n

3) Head For A Walk Down Michigan Ave Back Towards The City<\/h3>\n

You\u2019ve already had a little taste with Myopic Books and Stan\u2019s Donuts, but there are loads more fantastic shops and cafes on the way down through Wicker Park back towards the city center. You\u2019ll also find Wicker Park itself, should you want a big, green, open space to sit and relax awhile.<\/p>\n

If you can\u2019t make it the whole hour it\u2019ll take for you to walk to your lunch destination (or you can\u2019t trust yourself not to shop your credit cards out), there are always the trains or an Uber to help you.<\/p>\n

4) Lunch At Au Cheval<\/h3>\n

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<\/a> (800 W Randolph St) cheeseburger with egg is absolutely worth the wait.<\/p>\n

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 \u2013 watching the cooks at work while you\u2019re chowing down is pretty cool!<\/p>\n

\"Cheeseburger<\/p>\n

Day Three<\/h2>\n

1) Take A Hike Out Of The City And Head To Graceland Cemetery<\/h3>\n

No, a cemetery isn\u2019t a sightseeing location you usually see on a travel itinerary, but I\u2019m doing my best to change that. Graceland Cemetery & Arboretum<\/a> (4001 N Clark St) is one of the most stunning green spaces in the city, and the resting place of some of the city\u2019s most brilliant architects.<\/p>\n

If you\u2019re interested in some of the stories behind the graves, you can take a free self-guided audio tour. And if you\u2019re not so interested in history, the grounds are beautiful enough to make it worth the visit anyway.<\/p>\n

It\u2019s a fair way out of the city center, though, so you may want to take an Uber.<\/p>\n

\"Graceland<\/p>\n

2) Catch The Red Line Down To Lincoln Park<\/h3>\n

The scenic Lincoln Park neighborhood is enormous and has something for everyone. A nature museum, a conservatory, a harbor, a beach, a few cafes \u2013 there\u2019s even a zoo<\/a>!<\/p>\n

Whether you want to kill half an hour or spend half the day out there, it\u2019s a beautiful spot out on the water.<\/p>\n

3) Next Stop Is The Chicago History Museum<\/h3>\n

Chicago is a city with a lot of history (not all of it good), and the Chicago History Museum<\/a> (1601 N Clark St) presents the city\u2019s story in the best way possible. The exhibitions are larger than life and great for kids as well as adults.<\/p>\n

They draw you in in a way that makes them impossible to ignore \u2013 this isn\u2019t your standard boring school field trip museum. It also has a surprisingly good gift shop with some unique souvenirs to take home with you \u2013 my favorite was the umbrella I bought with the subway map printed on it.<\/p>\n

\"Chicago<\/p>\n

4) Enjoy A Bit Of Market Atmosphere At The Chicago French Market<\/h3>\n

In a city that has residents from all corners of the globe, the French Market<\/a> (131 N Clinton, between Washington and Randolph) is a collection of some of the city\u2019s best international food.<\/p>\n

Vietnamese, Cajun, Italian, Japanese\u2026take 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!<\/p>\n

Chicago 3 Day Itinerary Wrap Up<\/h2>\n

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!<\/p>\n

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<\/a>. Have fun in the Windy City!<\/p>\n

\n

We hope that this article has helped inspire you to visit Chicago. If you have any questions about the destination or have your own travel tips to share please leave these in the comments below. <\/i><\/b><\/p>\n

Want to share your own travel tips by guest writing for We Are Travel Girls? Go to our<\/i><\/b> Contribute<\/i><\/b><\/a> page for guidelines and to submit your article.<\/i><\/b><\/p>\n

\n

Pay Less, Travel More<\/h2>

Subscribe to get access to our FREE eBook with tips for saving money when you travel!<\/p>\n\t\t\t

\n\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t\t\n\t\t\t\t\r\n\t\t\t\t\n\t\t\t<\/form>\n\t\t<\/div><\/div><\/span><\/h6>\n
\n

Read More About Chicago<\/em><\/h4>\n