Create An Epic 3-Day Chicago Itinerary


If you are looking for the best things to do in 3 days in Chicago, where to go, and what to see, I hope this Chicago itinerary will help.

Chicago – one of the US’s largest cities – is full of interesting architecture and art, skyscrapers, parks, and even beaches. This city is a great place to visit for families and couples and solo travelers who want to see what the “Windy City” offers.

Though it might not be as famous as New York or Los Angeles, it surely is one of the most exciting cities in the US, with many beautiful places to visit and things to do.

The post was written by Rebecca

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But first, here are some travel tips to make your stay smoother.

How to Get to Chicago 

If you fly into Chicago, you will most likely come in via O’Hare International Airport, the busiest and third largest airport. You might also come to Chicago Midway International Airport.

If you are driving, you can take Interstate 90 whether you are coming from the south or north.

Once you arrive at the airport, you can either take a taxi or Uber to your hotel (costs about $30-40) or take the Blue Line.

The Blue Line ‘L’ Train leaves out of Terminals 1, 2, and 3 (follow the signs) and will take you from the airport to downtown in about 45 minutes. It costs about $5 ($2.50 if you are coming from Midway Airport). 

Weather in Chicago

Chicago has nice summers but cold winters. Summer temperatures are between 70ºF and 82ºF, while winter temperatures are between 22ºF and 32ºF.

The rainy season runs from June to August, and you will see the most snow in February. Summer is the best time to visit for outdoor activities, like beaches, rooftop bars, etc., but keep in mind the humidity is about 70% to feel a bit sticky. It is also one of the great spring and fall destinations to visit in the US:

What to Pack for a Your 3-Day Chicago Itinerary

Chicago weather is a little erratic, so the best way to dress is in layers.

Make sure you pack a jacket with your shorts and t-shirts for a summer trip because storms can come in quickly and drop the temps dramatically. This is also called the Windy City because the wind off Lake Michigan is common. 

For winter, pack a warm jacket, gloves, scarves, and boots. You might want to bring thermals to keep you warm under your clothes. And always bring comfortable walking shoes because you will probably do a lot of that here.

Where to Stay for 3 Days in Chicago 

Here are some places that are good options for your 3-day stay in Chicago.

  • For a luxury option, try the Peninsula Hotel, which provides great amenities, comfort, and location.
  • For a mid-range option, I would suggest the Kinzie Hotel. It’s close to the Magnificent Mile and offers a continental breakfast.
  • For budget accommodation, check out the Gateway Inn located in the Loop, which has nice clean rooms and isn’t far from some popular landmarks.

How to Get Around Chicago

The best way to get around Chicago is to use public transportation.

The Chicago Transit Authority (CTA) buses and trains are fast, cheap, and reliable. The trains are called the “L” because some of them are elevated (although some are underground, too). 

There’s also a free trolley that runs about every 30-45 minutes, but it can get pretty crowded, and you may have to wait for one that is empty enough for you to get on.

If you decide to rent a car, keep in mind that parking is expensive and hard to come by.

Chicago city downtown urban skyline

More Travel Tips

Get a CTA pass. If you plan to spend 3 days in Chicago and see multiple landmarks and take public transportation throughout the city, you will save yourself time and money by getting the pass. A 3-day pass costs $20 for unlimited rides over 72 hours.

Download the Transit app. If you’re using public transportation, this is an easy way to track routes and timetables for trains and buses. It even tells you when your stop is approaching so you don’t miss it.

Chicago is set up in a grid, which makes it easier to navigate than other cities. State Street and Madison Street meet in the Loop center in the middle of the grid, and street numbers fan out from there, going north/south and east/west. Keep this in mind when you are trying to figure out your routes. (Also, every 8 blocks equals about a mile.)

Traffic is pretty bad here, so make sure that you give yourself enough time to get places. Even when using public transportation, you will still experience some delays, so keep that in mind as you plan your days.

Tipping is a normal practice in Chicago, as in any American city, but a little higher than most. The standard is 20% of the bill. If you are getting drinks, then leave $1 per drink.

Being a large metropolitan city means higher security. Expect to get your bags searched at larger venues, and sometimes large bags are not permitted at all. Check the website of the places you will find out so that you aren’t turned away at the door if they don’t have lockers for you to use. Or travel light when you’re sightseeing.

If you are going to smaller venues or street festivals, make sure you’ve got the cash. Not all of them take credit cards, so cash is necessary at these places.

Chicago, like any city, has its good and bad neighborhoods. Use caution or avoid the sketchier areas and always keep an eye on your belongings. This is a safe city when you use common sense.


Let´s get started with your 3-day Chicago itinerary.


For our first day in Chicago, we will start with a bus tour. But not just any bus tour… 

The Untouchables Tour

The Untouchables tour celebrates Chicago’s infamous gangster past, and I highly suggest adding a tour to your Chicago itinerary.

This 2-hour tour covers all the famed locations and gives an account of Chicago in the 1920s and 1930s, including well-known mobsters like Al Capone. 

When the tour is over, head over to Chicago Riverwalk to stretch your legs and take in the sights, it should take about 10 minutes by train. Check out tours here.

Chicago Riverwalk

Located along the Chicago River, you can kayak here in warmer months or take a bike ride.

Northern Chicago River Riverwalk on North Branch Chicago River in Chicago, Illinois

There are also plenty of restaurants, benches for relaxing, and museums, like the Chicago River Museum. This is a good spot to stop for lunch or even enjoy a picnic if you get your food to go, and it is a must-see place and should be on any Chicago itinerary.

Plan in about 2 hours for this spot before heading to the next destination. This is about a 15-minute train ride north.

875 North Michigan Avenue / 360 Chicago Observation Deck

Located in the center of the city in the touristy Magnificent Mile, 875 North Michigan Avenue is the address of a supertall skyscraper that offers amazing views over Chicago.

City skyline from 360 Chicago observation deck. is one of the best things to see in 3 days

At 1,128 feet tall and 100 stories, this building’s upper floors put you in a unique perspective. Head up to the 94th floor for the 360 Chicago Observation Deck to enjoy the panoramic scenery.

You’ll be able to see many of the city’s neighborhoods, as well as Lake Michigan. If you feel like a thrill, then try Tilt – a moving platform that literally tilts you out over the street from the 94th floor! For the less adventurous, there is a very nice bar and café that you can stop in.

This will take about an hour or so. When this Chicago itinerary continues – take the train over to Navy Pier (about 15 minutes) or walk there (about 20 minutes). 

Navy Pier

This 3,300-foot-long Navy Pier juts out onto Lake Michigan and provides many entertaining options for the last stop of your day. 

Navy Pier and skyline is a must on any 3-day Chicago itinerary

If you have kids, you may want to stop at the Chicago Children’s Museum for some kid-centered fun. Or, if you feel like some exercise, rent a bike and explore on two wheels. 

Another fun thing to do is take a lake cruise – there are an architecture cruise and a classic lake tour that you can choose from. There are also dinner cruises if you prefer. Most last about 2 hours.

The Centennial Wheel is another must-stop on any 3-day Chicago itinerary. If you haven’t gotten your fill of rides and views, then try this 200-foot Ferris wheel that offers 360-degree views. Each ride lasts about 12-15 minutes.

Close out the night with dinner on the pier at one of its many lakeside restaurants, some even with rooftop decks (perfect for a warm summer’s night).

Navy Pier should take about 3-4 hours, depending on what you choose to do. Then, head back to the hotel for a busy Day 2.


Today, we are going to be doing a bit more city-wide traveling. But let’s start this Chicago itinerary for day 2 at one of the nicest parks in the city. So, head there after breakfast.

Millennial Park

Located in downtown Chicago, Millennial Park is full of things to do.

Crown Fountain in Millennial Park top place to see in 3 days
The Bean is a must for any Chicago itinerary
Pic: f11photo /

In the morning, I advise stopping at Lurie Garden for a bit of nature amid the urban environment. This garden is actually 2.5 acres, so there’s plenty to experience with its assortment of plants and flowers. 

This park also sports some interesting sculptures, like “the Bean,” a rock climbing wall, an open-air pavilion where you can catch live shows in good weather, and restaurants. This is a lot of fun for families and couples, and solo travelers who want to spend some time enjoying the outdoors in the middle of a metropolis.

While you could easily spend all day here, I would suggest keeping it to 3 hours so that you can see some more great attractions during your 3 days in Chicago.

Grab the train from the park to Buckingham Fountain (about 10 minutes away).

Buckingham Fountain

The beautiful Buckingham Fountain is one of the largest in the world. It was built in 1927 and inspired by one at the Palace of Versailles.

Buckingham fountain and Chicago itinerary

The wedding cake tiers of cascading water are beautiful and will make a great souvenir photo to bring home (or post on Instagram). 

Located in Grant Park, you can enjoy a stroll and relax in the sunshine for an hour before moving on to the next stop, which will be just a five-minute walk across Grant Park.

The Art Institute of Chicago

If you enjoy art, then take an hour or two to explore the Art Institute of Chicago, one of the country’s largest and oldest art museums.

Art Institute of Chicago on a 3-day itinerary for Chicago

Popular among visitors and locals, there are lots of exhibits to look over. And if you are visiting in the winter, this will be a beautiful place to warm up from the snowy chill.

But if you are not a huge art lover, then you can skip this stop (and the $25 ticket fee) and head to our next Chicago landmark. The train ride should only take about 10 minutes (15 if you walk).

Skydeck Chicago

The building was originally called the Sears Tower but is now Willis Towers.

Willis Tower Skydeck fun activity in 3 days

And up on the 103rd floor, you will find an amazing observation deck. As high up as it is, and with a 360-degree view, you can actually see four different states from this vantage point. 

If you happen to wait until later in the afternoon, you will be rewarded with a really spectacular sunset from here. 

Depending on lines (you can get a Fast Pass if you want to skip them), you will probably be here a little over an hour. Then, grab the train for a half-hour trek north of the downtown area. Check out ticket prices here.

North Avenue Beach

If you are visiting in the summer, this is a great place to stop. Favored by Chicagoans, you can enjoy some sand and sun, maybe even a swim or some water sports, during your afternoon here. 

Chicago downtown skyline

This is also a great place to grab a bite to eat, with casual eateries along the beach. There are stores if you want to do a little souvenir shopping while you’re here, too. Plan for about 2 hours at this spot.

Then, let’s head to a Chicago historical landmark that’s also a lot of fun. The train will get you there in about half an hour.

Wrigley Field

There’s nothing more American than baseball, and Chicago takes their baseball seriously.

Wrigley Field in Chicago a must see place

Wrigley Field was built in 1914 and is home to the Chicago Cubs. Restaurants, bars, and stores surround the field, so there’s something for even those who aren’t baseball fans. 

If you are curious about what a Major League park looks like on the inside, you can take a 60-90-minute guided tour and check out the dugouts where the players hang out the bleachers and more. This is a fun visit for adults and children alike.

Now, we are onto our last stop of the night, but only for the adults (sorry, kids). Take the train about 10 minutes north.

Green Mill

This lounge plays jazz and blues into the late night and is the perfect way to cap off your night.

The ambiance will remind you of the 1930s and 1940s, and you’ll love the energy here. Fair warning, though, there is a cover charge, and the bar only takes cash. So, plan and visit an ATM before stopping here for your nightcap.


For the last day of this 3-day itinerary in Chicago, we will start with a tour.

Chicago Trolley Tour

While we have definitely touched on many of Chicago’s best landmarks, it would be impossible to do it all in 3 days with a city this size.

Chicago Trolley at Chicago downtown best tips for 3 days

But the Chicago Trolley tour is a great way to see a few more spots before you leave town. 

This hop-on hop-off trolley will take you throughout different city areas, from the Magnificent Mile to the Chicago Theater to the Water Tower. And if you are visiting during the holidays, there are also holiday light tours, which are a lot of fun at night.

Depending on how much you hop off, this tour takes about 2 hours. When you’re done, we have a few more stops of our own.

Lakefront Trail

After sitting on the trolley, you may welcome the chance to walk, bike, or jog down this beautiful coastal pathway. It’s a trendy spot for enjoying the water and fresh air, as well as some outdoor activities, and so I think it should be on your 3-day Chicago itinerary.

Michigan Lakefront Trail in Chicago city, Illinois, USA

You’ll pass a lot of the city’s landmarks as you stroll along the path, but probably not all of it since it’s 19 miles long, and we only have one more day on this itinerary! Enjoy the views for an hour, and then let’s head to our next destination.

Adler Planetarium

The Adler Planetarium is perfect for the space lover in you. The oldest one in the world, you can see exhibits and projections of the stars in a dome-shaped night sky here.

Adler Planetarium in Chicago what to do in Chicago in 3 days

You will probably spend about 2 hours here, and our next stop is 30 minutes away by train.

The Garden of the Phoenix

This Japanese-style garden – the Garden of the Phoenix – is located on Jackson Park’s Wooded Island.


It’s a lovely place to slow down after a busy morning and afternoon seeing the sights of this bustling city. If you visit in May, you are in for a treat as the cherry blossom trees will be in bloom by then. The waterfall and footbridges are also favorite things to see.

You may spend an hour or two here. When you are ready, let’s head to the last location of this itinerary. The train ride should take about 20 minutes.

Promontory Point

This is our last stop on your Chicago itinerary. Plan to arrive in time to watch the sunset from Promontory Point Park.

I’d suggest getting dinner to go and picnicking here, where you can enjoy the city skyline as it reflects the setting sun and the changing colors of the sky.

Located in Burnham Park, it is a man-made peninsula that juts into Lake Michigan. You’ll get great views of the city and the lake from here. This is a perfect spot to say goodbye to Chicago.


I hope this 3-day Chicago itinerary will help you plan your own trip to the Windy City. If you were wondering what to do in 3 days, this list should help you find the best places for solo travelers, families, and couples to enjoy all that the city has to offer. It surely is one of the best places to visit in the US and always worth a trip.


About the Author:

This post was written by Rebecca, who runs her own blog at The Journey at Home – where she writes about her life as a mother of 5 with everything that comes along with it. She lived in New York for a long time before she moved to Las Vegas. She also works as a freelancer for Arzo Travels.

Safe Travels, Arzo

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