4 Days In Chicago – The Perfect Chicago Itinerary for First-Timers

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If you’re planning to spend 4 days in Chicago, you’re in for one of the country’s best blends of big city sophistication and laid-back charm!  Planning a trip to Chicago can be overwhelming, though, since there is so much to see and do.  I’ve put together this 4 day Chicago itinerary to help you plan the perfect experience for your first time in the Windy City.  Read on for more!

chicago travel guide itinerary

Before You Go to Chicago…

Make sure to get yourself one of these!  You’ll fit right in with the locals, who are still talking about 2016. 

Where to Stay in Chicago

I highly recommend staying at the Virgin Hotel in Chicago.  The hotel is perfectly located within walking distance to most of Chicago’s main sights, the rooms are super chic and modern, and I love some of the details and touches that are so iconic to the Virgin brand.

And get this: each room has a REASONABLY priced mini-bar.  What???  It’s true – you won’t be paying $8 for a Kit Kat here, folks.

But what I loved best of all about the Virgin Hotel is its rooftop bar.  It’s got an incredible view of the city, and particularly the city’s unique architecture.

The summer humidity in the midwest keeps the nights warm, so the rooftop bar is a great spot to unwind with a glass of wine after a day of sightseeing.

How Many Days Should You Spend in Chicago?

Chicago is located in the midwest, meaning that it’s well-connected by flight to other cities in the US.  Since it’s easy to get there, you might be wondering how much time you should spend in Chicago.

4 Days in Chicago is the Perfect Amount of Time to Spend in the City

If you’re planning a trip to Chicago, I recommend spending four days there.  With 4 days in Chicago, you’ll have plenty of time for all of the best things to do in Chicago, without feeling like you’re rushed.

In addition to the best sightseeing in Chicago, I’ve also included my recommendations for enjoying the city like locals do!

If you only have a weekend in Chicago

The itinerary in this guide is set up for 4 days in Chicago, but if you only have a weekend to spend in the city, it can be easily adapted for a weekend or long weekend in Chicago.  I recommend just picking and choosing from the activities below to customize your trip!

This 4 day Chicago itinerary includes something for everyone: food, sports, art, sightseeing, and exercise!  So depending on your priorities for your trip, you can mix and match the days below.

What is the best time of Year to Visit Chicago?

If you’re planning a trip to Chicago, you may be wondering what is the best time of year to visit Chicago.

Located in the Midwest, Chicago experiences all four seasons of weather!  Chicago is a vibrant city, and there are plenty of things to do during every season.

Spring and Fall are Great Seasons to Visit Chicago

If possible, plan your trip to Chicago in the late spring or early fall months.  June is a wonderful time of year to visit Chicago.  The weather is warm, and the locals are ready to celebrate after a long winter!

September is also a perfect time of year to visit Chicago.  The weather is still warm, but the city is less crowded.

In general, I would recommend avoiding winter months of January and February if you’re going to visit Chicago.  As someone who used to live in the Midwest, I can tell you that the weather in the winter is so cold, that it can be limiting to the activities you can do.

Pro Travel Tip: These days, travel can be more uncertain than ever. Check for any COVID-related restrictions at your destination, and never travel without travel insurance! I recommend SafetyWing, because they have flexible + affordable insurance plans, and also cover COVID-related impacts on your trip (not all companies do)!

Chicago Itinerary Day 1: Culture, Culture, Culture

Day one of your Chicago itinerary is all about soaking up some of the city’s iconic places and things to do.

Best Museums to Visit in Chicago

Chicago’s museums rival the best in the world, hands-down.  If it’s your first time visiting Chicago, I’d recommend my two favorites: The Field Museum and the Art Institute.

You can certainly pick between the two, but they’re both just THAT GOOD – that you should try to squeeze both in if you can!

Chicago travel guide itinerary

Get to The Field Museum first thing in the morning, to try and beat the crowds.  It’s an absolutely enormous museum, entirely dedicated to natural history.

The museum’s collections and specimens, along with the traveling exhibits that stop to call the museum home, are second to none.  From paleontology to the world’s butterflies, you’ll literally find it all here.

Get Your tickets for the Field Museum Ahead of Time

You can buy your tickets to the Field Museum online ahead of time, and have them sent straight to your email which I highly recommend. Get them here at this link, and cross one thing off your to-do list!

Next, head over to the Art Institute, another gem of a museum on a grand scale.    The Art Institute’s collections are incredibly comprehensive, so it’s hard to know where to start.

The museum is best known for its impressionist art, but you could literally spend days checking out all of the additional exhibitions.  It’s a design lover’s paradise.

Get Your Tickets to the Art Institute Ahead of Time

You can buy your tickets to the Art Institute online ahead of time, and have them sent straight to your email which I highly recommend. Get them here at this link, and cross one thing off your to-do list! And if you want to skip the line, you can also get FAST PASS tickets.

Millennium Park and The Bean

After museum hopping, it’s a quick walk over to Milennium Park.  It’s a great place to picnic for the afternoon, and check out the sculptural art that’s featured as part of the park.

Most famous is probably “the bean” – you know you’ve seen it on Instagram.

the bean at millennium park

The bean’s actual name is Cloud Gate, and it’s insta-famous for a reason!  Nearby Pritzker Pavilion is another cool sight, and looks (to me, anyway) like the cousin of the cornucopia from a Hunger Games movie.


Dinner and a (Sweaty) Show

For the evening, grab a casual dinner and indulge in some of Chicago’s most famous foods.  For Italian, check out Lou Malnati’s (including the oh-so-delicious deep-dish pizza that I am drooling just thinking about), or Jim’s Original for Polish sausage with peppers and onions.  Mmmmmmmm……

Chicagoans love their sports teams, so taking in a game for the evening is a great way to immerse yourself in the local culture.

In the winter, check out the Blackhawks or the Bulls home schedule, and in the fall, the entire Midwest revolves around football – so get yourself to a Chicago Bears game if you can.

In the summer, it’s alllll about baseball – you’ll just have to decide if you’re going to be a Cubs or a White Sox fan for the day.

Sun hat, heart sunglasses and phone sitting on rug.

free printable travel resources


Get ready for your next adventure with my free printable travel planners and packing lists – the perfect companions to make packing a cinch and keep you stress-free!

Chicago Itinerary Day 2: Views for Days

Start off the second day of your Chicago itinerary with an architectural tour of the city by boat.

You’ll cruise down the Chicago river with a guide, certified by the Chicago Architecture Foundation, who will walk you through an overview of 50 buildings along the river, woven through a narrative of the history of Chicago.

Honestly, this is a Chicago must-do!  

Buy Your Architecture Tickets Online Ahead of Time

For the tour, I recommend that you buy tickets ahead of time online. The tours are popular and can fill up early, so it is a good idea to book in advance to secure the date and time you want to do your tour.

Chicago travel guide itinerary-3

Skydeck at Willis Tower for Views Galore

After the tour, get another perspective on the city’s architecture with a view from up above by visiting Skydeck Chicago an observatory among the clouds, located on the 103rd floor of the famous Willis Tower, formerly known as the Sears Tower.

The observatory offers stunning views of the entire City of Chicago, as well as the coastline of Lake Michigan.  It truly gives you a sense for the expanse of the lake, because it’s so big that it seems more like an ocean!

While you’re visiting the Skydeck, make sure to check out The Ledge, where you can stand against a piece of glass that tilts out over the street.  Even the fearless will get a little bit of a thrill!

You can buy your tickets to Skydeck Chicago online ahead of time, and have them sent straight to your email which I highly recommend. This is one of the most popular tourist attractions in Chicago, and it can get busy! Get them here at this link, and cross one thing off your to-do list!

Lake Michigan shoreline in chicago

Explore Lincoln Park Boutiques

Once you’ve gotten your fill of sky-high views, catch a ride up to Lincoln Park, one of North Side Chicago’s trendy residential neighborhoods, and named for the city’s largest park, which is the lakeside centerpiece of this part of town.

Lincoln Park is One of the Best Neighborhoods to Visit in Chicago

The Lincoln Park Zoo and Lincoln Park Conservatory are both fun to wander through, but I love Lincoln Park for its cafes, boutiques, and adorable homes.

Armitage Avenue is a perfect spot to boutique-hop for the afternoon.  I love Art Effect for cute gifts (and travel accessories!), and Interior Define is fun to check out for home decor.

If it’s one of those hot, sticky midwestern summer days and you’re not up for shopping, check out one of the nearby beaches along Lake Michigan.  North Avenue beach is a local favorite.


Dinner and Dates

End your evening with dinner at Avec, an adorable, modern and warm spot where you can dine tapas-style.  You absolutely must order the chorizo-stuffed dates.  Holy moly, they are incredible!!!

You can thank me later.  After dinner, enjoy some classic Chicago nightlife with either a live jazz performance at Buddy Guy’s Legends, or a comedy show at Second City.


Chicago Itinerary Day 3

Kick off the third day of your 4 day Chicago itinerary with brunch at Taureaux Tavern, a French-inspired bistro in the Loop that is basically a brunch-lovers paradise.  And indulge!  You’ll walk it off later today.

Explore Navy Pier

After you’ve had your share of pastries galore, head over to Navy Pier, a Chicago landmark on Lake Michigan filled with parks, shops, restaurants and event space – there’s always something going on there!

Take a ride on the Centennial Wheel, or check out the Navy Pier event calendar for the latest and greatest of what’s going on.

Although I haven’t experienced this myself, I just saw that Navy Pier shows outdoor films during the summer months, which would be a really fun thing to do while visiting Chicago.

Ferris wheel at navy pier

Check out the Shedd Aquarium

Spend the rest of the day visiting the Shedd Aquarium, one of the best places to visit in Chicago.

The Shedd Aquarium is another one of Chicago’s finest – it’s an ENORMOUS indoor aquarium and if you’re traveling to Chicago with kids, they’ll fall in love immediately with the exhibits and animal experiences.

Buy Your Shedd Aquarium Tickets Online Ahead of Time

You can buy your tickets to the Shedd Aquarium online ahead of time, and have them sent straight to your email which I highly recommend. Get them here at this link, and cross one thing off your to-do list!

Chicago Itinerary Day 4

Shopping on Michigan Avenue

No trip to Chicago would be complete without a stroll up Michigan Ave and the Magnificent Mile, so head in that direction to kick off your last day in the city.

Most of the shops here are super high-end (think Gucci), so if you’re like me, you’re mostly window shopping, but it’s still fun to walk along and enjoy what is Chicago’s version of NYC’s Fifth Avenue.

Chicago’s Lakefront Trail

I promised we’d do a lot of walking today, so next, head back towards Lake Michigan and enjoy the lakefront trail, a nearly 20-mile stretch of paved walkway that meanders down the city’s coastline.

The views are spectacular and it’s a great way to see the city’s skyline from a distance.   If you’d prefer to bike the trail (highly recommended!), check out the city’s bike-sharing system, Divvy, where you can grab a bike for a 24-hour rental period from one of the city’s many stations

Dinner at Girl and The Goat

Wrap up the day with dinner at Girl and the Goat, my hands-down favorite restaurant in Chicago.  Go early or make a reservation, because this is one popular spot (but you’ll see why once you visit)!

End your evening and toast to your time in the Windy City with cocktails at one of Chicago’s rooftop bars.  I like Cindy’s at the Chicago Athletic Association for lakefront views and a chic scene, but there’s plenty of places to choose from!

Save Money on Sightseeing With The Chicago Explorer Pass

If you’re planning to do some sightseeing while you’re in Chicago, you will save money by buying the Chicago Explorer Pass. You can choose from visiting 3, 4, or 5 of Chicago’s most popular sights, including the Shedd Aquarium, Skydeck Chicago, an Architecture Cruise, the Field Museum, and a ton more. The pass downloads to your phone so it’s super simple to use, too. I highly recommend it! You can get the Chicago Explorer pass here at this link, and cross one thing off your to-do list!

There you Have it – The Perfect 4 Day Chicago Itinerary!

If you love to explore cities like Chicago, you’ll love checking out this Portland 2 day itinerary, a Toronto itinerary written by a local, as well as The Big Apple with my perfect 5 day New York itinerary!

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  1. Thanks so much for including us on your itinerary! If you’re visiting Chicago and our head our way, complete the afternoon with chocolate at Vosges, right across the street and a coffee at La Colombe a few short blocks down. So much to explore!