4-Day Chicago Itinerary: Best Things to Do, See, and Eat
If you’re planning a trip to Chicago and want to make the most of your time, you’ve come to the right place!
I’ve lived in Indianapolis my whole life and have visited Chicago numerous times since it’s only about a 3-hour drive away.
I’m a big fan of Chicago, especially during the summer, and my husband and I always try to make a weekend trip there each year during the summer or fall.
My favorite things about Chicago are how walkable it is, how easily accessible Lake Michigan is (walking along the lakeside trail is my favorite thing to do in Chicago!), and just the overall vibe of the city.
In this post, I’ll walk you through a detailed 4-day Chicago itinerary that includes all of my favorite things to do in Chicago, along with tips on how to get around using public transit, where to stay, and all the best food to try!
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Quick at a Glance: Where to Stay & What to Do
If you’re short on time, here are my top recommendations on things to do in Chicago as well as recommend places to stay!
Where to Stay:
What to Do:
4-Day Chicago Itinerary
4 days in Chicago is a great amount of time to see the main tourist spots and also have time to get off the beaten path and explore some of the neighborhoods.
My favorite thing to do in Chicago is to just walk around and explore different areas.
Every neighborhood feels a little different, and there’s always something interesting to see!
I would definitely make sure to set aside some time in your itinerary to just walk around and explore!
I created a Google Map with everything from this 4-day Chicago itinerary pinned so it’s easy to see where everything is and get walking or public transit directions.
Day 1: Chicago’s Most Iconic Sights
If this is your first time visiting Chicago, I recommend starting off your trip by knocking out some of the most famous spots in the city.
Millennium Park, the Bean, and the Willis Tower are all located close together, so it’s easy to do them all in one day.
Breakfast at Wildberry Pancakes & Cafe
Depending on when you arrive in Chicago on your first day, I recommend grabbing breakfast from Wildberry Pancakes & Cafe, which is right across the street from Millennium Park.
They’re known for their pancakes, but everything on the menu is really good!
Their breakfast burrito and butcher block skillet are really good options if you’re craving something more savory.
See the Sights in Millennium Park
After breakfast, head across the street to Millennium Park to see the Bean (formally called Cloud Gate).
It’s a classic photo spot to snap a selfie in its reflective surface and early morning is a great time to go before it gets super crowded.
From there, you can walk around the park to see the Crown Fountain and Lurie Garden.
Visit Willis Tower and Go to the Skydeck
Next, head to the Willis Tower and go up to the Skydeck.
It gives you panoramic views of the entire city, and you can step out on The Ledge, a glass balcony that hangs over the edge (if you’re not afraid of heights!).
I recommend booking your tickets ahead of time to skip the line. You can book your tickets here or below.
Go Shopping at Magnificent Mile
In the afternoon, head to the Magnificent Mile, which is a stretch of Michigan Avenue that is filled with a ton of shops and restaurants.
Even if you’re not big into shopping, it’s a nice area to walk around and people watch.
Day 1 Summary
- Breakfast at Wildberry Pancakes & Cafe
- Walk around Millennium Park and take photos with The Bean
- Visit Crown Fountain and Lurie Garden
- Go to the top of the Willis Tower Skydeck
- Explore the Magnificent Mile and go shopping (Michigan Ave)
If you’re short on time, be sure to check out my one-day Chicago itinerary as well!
Day 2: Lakefront & Lincoln Park Neighborhood
This is probably my favorite day of the itinerary, and if the weather is good, I recommend spending as much of it outside as possible!
Walking Along the Lakefront Trail
I recommend starting your morning with a coffee and walking along the Lakefront Trail.
In my opinion, the lakefront trail is one of the best things about Chicago!
The combination of the views of Lake Michigan, the city skyline in the background, and the beaches where you can lay out or swim, make it one of the best parts of Chicago.
It is not something you find in most big cities which I think makes it so unique!
In the summer, Oak Street Beach and North Avenue Beach are great places to lay out or even swim.
It is such an active area as well, we saw people swimming in the lake, playing beach volleyball, or just running, walking, or biking along the concrete trail.
You can get on the trail from many different spots since it’s about 18.5 miles long. Use this AllTrails map to find the best spot to get on based on where you’re coming from.
Explore the Lincoln Park Neighborhood
After a relaxing morning along the lake, I recommend heading north towards the Lincoln Park neighborhood, which is one of my favorite areas in Chicago!
It has such a great vibe with cute streets, historic homes, and great nature.
There’s also a farmers market on weekends (usually Saturday mornings), which is worth stopping by if your timing works out.
You can visit the Lincoln Park Zoo, which is free to enter, or walk through the Lincoln Park Conservatory if you’re into plants.
I’m not the biggest fan of zoos, but I still think it’s cool that this one is free and right in the city.
We also visited a dog-themed coffee shop in Lincoln Park that I loved called Ludlow Charlingtons. They had a really good seasonal drink menu!
Day 2 Summary
- Morning coffee and walk or bike on the Lakefront Trail
- Hang out at North Avenue Beach or Oak Street Beach
- Explore the Lincoln Park neighborhood
- Visit the Lincoln Park Zoo (free!) or Conservatory
- Check out the farmers market (Saturday mornings)
- Coffee stop at Ludlow Charlingtons
Day 3: Chicago River & Navy Pier
Today is all about exploring the city by the water!
Join a Chicago River Architecture Cruise
One of the best things you can do in Chicago is the Architecture River Cruise.
These boat tours take you down the Chicago River and give you the background on the city’s architecture and history.
It is a great way to enjoy the warm weather on the water and learn about Chicago’s history.
I recommend booking in advance, especially during weekends in the summer! You can book your tickets here or below.
Walk Along the Chicago Riverwalk
After your cruise, take some time to walk along the Chicago Riverwalk.
Here is a map of a route you can walk.
There are plenty of restaurants and places to grab a drink or a snack, plus it’s just a really scenic walk.
I really like Pizzeria Portofino which is located right along the Chicago River!
Explore Navy Pier
In the afternoon, I recommend heading over to Navy Pier.
Yes, it’s touristy, but it’s worth visiting at least once. You can ride the Centennial Wheel, walk through the pier, and get some great views of the lake.
If you’re interested in riding the Centennial Wheel, you can book tickets in advance here or once you get there.
Day 3 Summary
- Architecture River Cruise (book ahead here!)
- Walk along the Chicago Riverwalk
- Afternoon at Navy Pier
- Ride the Centennial Wheel
Day 4: Local Food Tour & History
For your last day in Chicago, I recommend focusing on the city’s culture and food.
You can’t go wrong by starting your day with coffee and a sweet treat from Stan’s Donuts or Doughnut Vault!
If you’re more of a bagel person, we went to Schneider Deli, and it was delicious! You can get hashbrowns on your bagel which is a must.
Learn About Chicago’s History
On your final day, take the time to explore Chicago and learn about its history.
You can join a unique walking tour to learn about a uniqueside of Chicago on this Gangsters and Ghosts Guided Walking Tour.
You can book the tour here or below.
If you’re not really into history, I would recommend spending more time outside at Grant Park instead.
It’s a huge green space right in downtown Chicago and includes the popular Buckingham Fountain.
It’s a great spot to walk around, relax, or just take a break from the busy city.
If you’re traveling with kids, be sure to read my blog post where I cover 27 free things to do in Chicago with kids!
Join a Local Food Tour
A fun way to explore the city is to go on a food and walking tour with a guide to try out all the best local foods!
This food and walking tour on Viator is highly reviewed and recommended! It includes 4 to 5 food stops including deep dish pizza and Chicago-style hot dogs!
You can book the tour here or below if you’re interested!
If you would rather make your own version of a food tour, I recommend trying the following foods:
- Chicago-style hot dog at Portillo’s
- Italian beef sandwich at Al’s
- Deep dish pizza at Lou Malnati’s
- Garrett’s Popcorn (I love the carmel and cheddar cheese mix!)
Catch a Baseball Game
If the Cubs or White Sox are in town, a baseball game is a really fun way to wrap up your trip.
Wrigley Field (where the Cubs play) has so much history and the surrounding Wrigleyville neighborhood is full of bars, restaurants, and fun energy even if you’re not a huge baseball fan.
Day 4 Summary
- Morning stop at Stan’s Donuts or bagels at Schneider Deli
- Join a Gangsters and Ghosts Walking Tour
- Relax in Grant Park
- Join a walking food tour of Chicago’s classic foods or DIY your own!
- Optional: Cubs or White Sox baseball game
Best Places to Eat in Chicago
Here’s a list of my favorite places to eat in Chicago and must-try food items:
- Bavette’s Bar & Boeuf – Hands down, the best place I have ever eaten in Chicago! It’s a steakhouse with incredible food and a speakeasy-style vibe. Definitely make a reservation in advance or show up right when they open to sit at the bar. I love their Wagyu Cheeseburger!
- La Colombe – Great coffee with multiple locations around the city.
- Portillo’s – A Chicago staple, Portillo’s is famous for its hot dogs, Italian beef sandwiches, and milkshakes. It’s a must-try for a casual and iconic Chicago meal!
- Lou Malnati’s – If you’re in Chicago, you must try deep dish pizza, and Lou Malnati’s is one of the best spots!
- Margie’s Candies – If you’re craving a sweet treat, Margie’s Candies is the place to go! They serve huge ice cream sundaes.
- The Leavitt Street Inn & Tavern – A go-to spot for delicious smashburgers!
Best Places to Stay in Chicago
I usually always stay in Hyatt hotels in Chicago since I use the majority of my Chase Ultimate Reward credit card points to redeem free nights at Hyatt hotels.
They offer great deals on nights with points, and I’ve always had great experiences staying at Hyatt hotels.
I have stayed at the Hyatt Regency Chicago and the Hyatt Place in River North and recommend both!
If I had to choose one, I think I would choose Hyatt Place in River North. It is in a great location and had plenty of restaurants nearby.
Here are some other recommended places to stay in Chicago that are highly reviewed:
- The Gwen, a Luxury Collection Hotel – Great views and right off the Magnificent Mile.
- 21c Museum Hotel Chicago – Modern boutique hotel
- CitizenM Chicago Downtown – Affordable, and close to downtown sights. The rooms are smaller than your typical hotel room.
- Viceroy Chicago – Stylish hotel in the Gold Coast with a rooftop bar
Check out this interactive map below for even more places to stay in Chicago!
Best Time to Visit Chicago
I think the best time to visit Chicago is from May to October, preferably during the summer months (June through August).
I think Chicago during the summer is at its best with plenty of events happening, the lakefront is lively, and the weather is perfect for walking around.
Spring and fall are nice too, specifically May and October, but I would pack layers with you just in case it is chilly in the mornings and evenings.
Winters are cold, windy, and snowy, so I usually avoid visiting during that time if I can. The lakefront, which is my favorite part of Chicago, is harder to enjoy in the winter.
If you’re visiting Chicago in winter, check out my blog post all about things to do in Chicago in winter!
Flights to Chicago
I’ve only ever driven into Chicago since we live in the Indianapolis area, which is only about a 3 hour-drive from the city.
If you don’t live within driving distance or would prefer to fly, I recommend flying into Chicago O’Hare International Airport.
It’s Chicago’s main airport and has numerous direct flights from across the country and internationally.
There’s also Midway Airport, which is a smaller airport but still fairly close to downtown Chicago.
So, you could check both airports to see where your flight is cheaper.
It will most likely be cheaper at Chicago O’Hare International Airport!
From both of these airports, you can take public transit (the CTA Blue Line from O’Hare and the Orange Line from Midway) to get downtown.
You could always use Uber or Lyft, but it will be more expensive.
You can use Expedia to find the best flight deals!
Do You Need a Rental Car in Chicago?
I would not recommend renting a car in Chicago.
Chicago has great public transportation that is well-connected, and it is also a very walkable city!
I usually always get over 20k steps a day in Chicago which can be exhausting, but I think walking is one of the best ways to explore a city!
Also another reason to not rent a car in Chicago is that parking can be hard to find and is usually pretty expensive.
Since we drive to Chicago, we park our car at the hotel, and it usually costs around $40 to $50 per night 😢.
Between the CTA (public transit), walking, and the occasional Uber or Lyft ride, you will be able to get around Chicago just fine without a rental car.
How to Use Public Transit in Chicago (CTA)
Chicago has a great public transit system run by the CTA (Chicago Transit Authority), which includes both trains (called the “L”) and buses.
It’s one of the easiest ways to get around the city without a car.
- L Trains: The trains are color-coded (like the Red Line, Blue Line, etc.) and connect to most major parts of the city. The Red and Blue Lines run 24/7.
- Ventra Card: You’ll need a Ventra Card or the Ventra app to pay for rides. You can buy a card at vending machines in most L stations or load money onto the app. I recommend using the app!
- Google Maps: I recommend using Google Maps for directions. Just enter your destination, click the transit icon, and it will tell you exactly which train or bus to take, when it’s arriving, and where to get off. It is so helpful!
- Late Nights: If you’re out late, Uber or Lyft is a good option!
You can also visit transitchicago.com for maps, schedules, and more information.
Final Thoughts on Spending 4 Days in Chicago
Chicago is one of my favorite cities to visit!
It’s super easy to get around by walking or using public transit, there’s always something going on, and honestly, the food alone is worth the trip (make sure to go to Bavette’s Bar & Boeuf)!
I hope this 4-day Chicago itinerary helped you plan your trip and gave you a good idea of things to see, do, and eat.
If there is one thing you must make time for, it is walking along the lakeside trail. It is my favorite thing to do in Chicago!
Let me know if you end up visiting, I would love to hear what you thought of Chicago!
Check out my other Chicago blog posts to help plan your trip!
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