Best 4 Day Chicago Itinerary

Looking for the Best 4 Day Chicago Itinerary?  I have got the guide for you!


Dramatic skyscrapers above deep blue water paint the backdrop for America’s Windy City, Chicago.  Located in the midwestern United States, Chicago is sometimes overshadowed by bustling New York City and dreamy Los Angeles- but it’s no less iconic.  


Chicago has made a name for itself as the third largest city in the United States.  Featuring famous festivals, delicious food, and Broadway shows, there is a little something for everyone in Chicago.


Come for the Chicago Cubs and stay for historical architecture, free beaches, unique neighborhoods, and hidden pockets to explore.  No matter your travel style, Chicago has something to show off to everyone.  

Chicago Skyline

The Details

Location: Midwest United States

When to visit: Spring and summer are Chicago’s most popular seasons of the year.  Beautiful weather makes way for outdoor festivals and endless exploring.  Fall has beautiful hidden foliage locations with mild-cold temperatures depending on the year.  Winter sees near freezing temperatures, but is also a magical wonderland featuring Christmas Markets and classic seasonal events like ice skating 

How many days: A 4 day Chicago Itinerary allows visitors to explore Chicago’s iconic locations and hidden spots at a relaxed pace.  Stay longer to experience even more of Chicago’s culture and take a day trip to Indiana Dunes National Park or Starved Rock.  If you only have one day in Chicago, scratch the surface and cross your top items off your list. 

Getting there: Fly into Chicago’s O’Hare International Airport or Midway International Airport.  Rent a car from the airport or take public transportation to your accommodation and consider using rideshare, public transportation, biking, or walking around the city.  

Streeterville, Chicago

Things to Do in Chicago

There are LIMITLESS things to do in Chicago, so the following items provide a combination between can’t miss spots, and local favorites. 

Millenium Park

Millenium Park, Chicago

First thing’s first- the architecture!  The city’s architecture boasts some of the best photography spots in Chicago.  Millennium Park is one of Chicago’s most visited destinations housing its iconic “Bean” or Cloud Gate sculpture.  It’s located just a block from Chicago’s equally famous Grandt Park. 

Navy Pier

Chicago’s infamous  Navy Pier boasts incredible skyline views year-round.  Consider taking a walk, attendig a seasonal event, grabbing a bite to eat, or taking a ride on its famous ferris wheel.  Parking at the on site garage is convenient but expensive.  

Chicago Museums

Adler Planetarium, Chicago

Just outside the Adler Planetarium is one of the best views of Chicago!  Visitors can pack a picnic and sit on the many steps outside of the Planetarium overlooking Chicago’s skyline above Lake Michigan.  Nearby, consider the Field Museum for its annual themed exhibits, Museum of Science and Industry, or the Art Institute. 

Skyline Views

Chicago Skyline

A 4 day Chicago Itinerary is not complete until you have experienced some epic skyline views.  There are limitless locations to see Chicago’s beautiful skyline.  Consider splurging on Tilt tickets, visiting a rooftop (advanced reservations often required), or along Lakeshore Drive.

Chicago Tours

Chicago Architecture

Chicago’s Architecture tours are highly acclaimed by both locals and visitors.  Budget travelers- consider a free walking tour.  I love getting my bearings set in a new city on a free walking tour.  Alternatively, consider a bike, e-bike, or scooter tour.  

Chicago Shows

Chicago Theater

Chicago’s Broadway features a plethora of year-round performances.  For something different, consider tickets for Blue Man Group, or for something more lowkey, check out a local comedy club.

Chicago Sports

Wrigley Field, Chicago

Chicago is also famous for its sports- specifically its Cubs vs. White Socks rivalry.  Catch a Chicago Cubs or Chicago White Socks game over the summer, a Chicago Bears game in the fall, or a Chicago Bulls game in the spring. 

Chicago Neighborhoods

Lincoln Park Skyline, Chicago

Chicago has approximately 77 neighborhoods.  Consider exploring Wicker Park for its eclectic and hipster atmosphere.  Trendy Bucktown and Logan Square are right next door, often more expensive featuring fine dining options and higher costs.  Lincoln Park houses a free conservatory (with timed ticket entry secured online in advance) and beautiful skyline views. 

Seasonal Things to do in Chicago

Spring in Chicago

Tulip bulbs light up Michigan Avenue, and Cherry Blossoms flood Jackson Park each spring.  Chicago Cubs begin their season in March!  Many March visitors also enjoy watching the infamous Chicago River being dyed green for St. Patrick’s Day before watching Chicago’s parade.  This historically occurs the weekend before St. Patrick’s day.

Summer in Chicago

Chicago summers are known for lowkey gatherings like spacious patios, and for bigger events like Taste of Chicago. 

Fall in Chicago

Fall makes way for pop-ups like Jack’s Pumpkin Patch, and is famously known for its annual Chicago Marathon.  

Winter in Chicago

There are limitless fun things to do in Chicago in the winter despite its low temperatures! Winter in Chicago is a big hit with Ice Skating in Maggie Daley Park, two Christkindl Markets, and several Christmas-themed pop-up spots. 

Where to stay in Chicago



Chicago’s most budget friendly option is hostel dorms at approximately $45/night.  Private hostel rooms can be comparable prices to mid-range hotels.  Consider highly rated Freehand Chicago or Chicago Getaway Hostel.  


I would not consider hotels in Chicago to be budget-friendly.  Consider staying in a local suburb near a train station if you do not mind commuting into the city each day of your trip (though this is a cost of itself)




The Drake is one of Chicago’s highly acclaimed hotels.  It’s popular for weddings, high tea events, and of course for an overnight stay.  The Drake Chicago falls somewhere in between the Mid-Range and Luxury category, depending on time of year and rates change consistently.  




The Swissotel’s prime location makes it an ideal stay for visitors.  

Things to do near Chicago

Adding days to your Chicago itinerary or looking to get out of the city?  Consider exploring Indiana Dunes National Park or Starved Rock State Park.  For Starved Rock, I recommend car rental.  For Indiana Dunes, there is a direct train line that takes you to the  national park from Chicago Union Station.  Map out your hiking trails in advance to determine how far you would be walking to begin a hike, and if car rental for one day makes most sense. 

Chicago Packing List

Here are a couple of can’t-miss items to toss in your suitcase when completing a 4 day Chicago itinerary.

Supportive Shoes– A lot of exploring means a lot of walking.  Comfort is key when exploring the windy city!  

Water bottle– I always recommend a water bottle for long days exploring.  Hydrate, hydrate, hydrate!

Packable backpack– if this is what you fancy!  Love it because it collapses/folds so easily into your travel suitcase or backpack.  It’s an ideal size for day exploring.  

For Winter weather…

Winter jacket– The freezing winter temperatures are no joke.  Pack the jacket!  This puffer jacket is collapsible and easily compresses into a backpack or suitcase. 

Boots– Bring a pair of comfortable walking boots so the snowy sidewalks do not limit your exploring!  I enjoy wearing waterproof hiking boots when exploring in snowy weather.  

In the spring…

Umbrella– Take a travel umbrella for sure!  Spring rain in Chicago is unpredictable.  

Rain Jacket– Keep a lightweight rain jacket handy because it the spring you just never know.  I wear the same rain jacket for city exploring that I use on my day hiking trips.  

Rain Boots– Or water resistant hiking boots (which I find so comfy!)


Sandals– Carry a pair of sandals or flip flops in your bag in case you decide to lounge at the beach in between exploring

Travel Towel– I recommend this too, for a random beach stop, if it fits in your bag!  It’s so light weight and easy to take on the plane.  


Fleece jacket– A warm fleece jacket is ideal this time of year.  

Layers– Layer up with some packable, light, long sleeve shirts in your bag.  

Winter jacket– Check the weather ahead of time.  There is an equally high probability you will need a winter jacket, and equally high that you will not.  

4 Day Chicago Itinerary

Day 1

Relish Hot Dogs, Chicago

Your first day conveniently begins near Chicago Union Station, in case you arrive via train from the airport or a local suburb  in the morning.  Start the day walking from Union Station to your museum of choice: Field Museum, Museum of Science and Industry, or the Art Institute.  


Then, grab a Chicago-style hot dog from Relish Hot Dog stand outside of the museums.  (Vegetarians- they got you covered!)  


Walk to Millenium Park and enjoy your hotdog picnic here.  You’ll want to have your cameras ready for classic Chicago photo spots like The Bean (also known as Cloud Gate) or the water screens.  Walk to Lurie Garden and check out flower blooms (in the summer) while admiring skyscrapers- got it all!  


Explore Grant Park just a block over.  


Walk along State Street.  Shoppers- you will be happy!  Snap a photo with the iconic Chicago Theater sign.  


Eat dinner.  


*More time?  Add-ons for today:

-Chicago Museum of Culture (Free)- across from Millenium park.  

Chicago is timeless, and I highly recommend you enjoy a visit when you get the chance.  

Day 2

Begin your day high above the city in a skyscraper.  Budget travelers- choose just one to visit.  Visit the John Hancock Building, Willis (Sears) Tower, or purchase tickets for the Chicago Tilt or Skybox.  Tickets are expensive and you can get incredible views from free locations too, so set your priorities accordingly.  


Cruise along Michigan Avenue.  

Day 3

Wicker Park, Chicago

It’s time to get out of downtown and visit Chicago’s unique neighborhoods.  Begin your morning walking or biking on the 606 Trail.  This 3 mile walking trail sits above Humboldt Park, Wicker Park, Bucktown, and Logan Square.  You can hop on at many different entrance points through the neighborhoods and hop off when you want to explore or grab a bite to eat.  I recommend prioritizing Wicker Park for its fun, hipster atmosphere (It gives me Red Arts District, Asheville vibes).  

Day 4

Lincoln Park Conservatory, Chicago

On your fourth and final day in the Windy City, take a day trip or contine your neigbhorhood exploring. 

There are a lot of things to do in Lincoln Park, Chicago!  Begin the day visiting Lincoln Park Conservatory for free- just reserve your timed entry ticket online in advance.  

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As a full time employee who loves her job, learn how I honor my wanderlust while working a 9:00-5:00 (because I want to!) This blog welcomes all, and specifically provides resources for those seeking travel intertwined into a busy schedule (3 days to 5 weeks).