Unforgettable Chicago 4-Day Itinerary
Chicago is one of the most beautiful cities, with stunning architecture, delicious deep-dish pizza, a beautiful lake, and the only river in the world that flows backward. Since Chicago is a large city, you could spend an entire week exploring everything it offers.
If you do not have a week to spend in the city, you can spend 4 days in Chicago exploring most of the must-see attractions. This guide has everything you need to know to create the best Chicago 4-day itinerary!
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Tips For Visiting Chicago
Helpful Itinerary Information
Buy a transit pass. The transit system in Chicago (the CTA) is easy to use and can take you to many must-see attractions. You can purchase one-day, three-day, or seven-day Ventra Cards for your trip. I recommend buying a multi-day ticket.
Walk or rent Divvy Bikes if you don’t like public transit systems. Chicago is walkable, so I recommend walking through the city, especially since it’s free! Divvy Bikes have thousands of bikes around Chicago, so you can pick up and drop off bikes wherever needed.
Look for discount cards and passes. Your trip to Chicago does not have to be expensive. There are many ways to save money, including the Chicago CityPASS, discount cards, discount codes, or purchasing tickets in advance to must-see attractions. There are also many free things to do in Chicago!
Pack layers. The weather in Chicago can be unpredictable, and Lake Michigan can create drastic temperature changes and high winds. I recommend packing a rain jacket for the warmer months and many layers.
Where to STay in Chicago
Chicago is a large city with many neighborhoods, and I recommend staying in The Loop/Downtown Chicago, River North, Streeterville, and Gold Coast because they are safe and near most must-see attractions. There are many hotels in these neighborhoods for all budgets.
Hotels in Loop/Downtown Chicago
Hotels in River North
Hotels in Streeterville
Hotels in Gold Coast
Best Restaurants in Chicago
When you visit Chicago, I recommend trying the delicious food in the city! Chicago has so many incredible places to eat, so you cannot go wrong with any restaurant you choose. Here are only a few of the best restaurants in Chicago!
Giordano’s Pizza - incredible pizza
Lou Malnati’s Pizzeria - some of the best pizza I have ever had
Lou Mitchell’s - the best breakfast diner
The Village - the oldest Italian restaurant in Chicago with delicious food
The Purple Pig - an overall delicious restaurant
BomboBar - amazing desserts
The Best Chicago 4-Day Itinerary
This Chicago 4-day itinerary has many must-see attractions, including art museums, architecture tours, sports events, theaters, and zoos. Chicago has an incredible transit system that is easy to use and brings you anywhere you need in Chicago, including the airport.
There are two airports you can fly into that offer many flight options. Chicago O’Hare International Airport is the largest airport and is an hour train ride to downtown Chicago. Chicago Midway International Airport is the second largest airport in Chicago and is only a half-hour train ride to downtown. Chicago is also easy to navigate if you prefer to walk!
Pro tip: Purchase the Chicago CityPASS if you want to see the highlights of Chicago. The pass provides admission to many of the must-see attractions.
Day 1 in Chicago
Your first day in Chicago has many iconic attractions in Chicago north of the Chicago River and is more of a relaxed day.
The Magnificent Mile is an iconic street in downtown Chicago with everything, including restaurants, luxury stores, and upscale shops. You can spend the day walking the Magnificent Mile and exploring the area.
Time needed: 2-3 hours
Price: free
How to get there: The State/Lake station
The 360 Chicago Observation Deck is at the top of the John Hancock Building and is home to Chicago’s tallest thrill ride, the TILT, and Chicago’s highest bar, BAR 94. The TILT allows riders to extend out of the John Hancock Building 1,030 feet high, offering a unique way to see Chicago! It’s perfect for anyone looking for a thrill!
Time needed: 1-2 hours
Price: $30
How to get there: The Chicago station
The Chicago Theater is an iconic landmark in Chicago, offering a variety of Broadway shows, concerts, and musicals and the perfect way to end the first day of your 4 days in Chicago. It is known as the unofficial symbol of Chicago and is in many famous movies, television shows, and photographs.
Time needed: Varies by the show
Price: Varies
How to get there: The State/Lake station
Day 2 in Chicago
Your second day in Chicago has many must-see attractions south of the river!
Millennium Park is located on the lakefront in downtown Chicago and has beautiful art throughout the campus, including the iconic Cloud Gate statue. The Cloud Gate Statue (aka The Bean) is one of the most famous attractions in Chicago and offers an incredible reflection of the city skyline. Not too far from The Bean is the Crown Fountain. The Crown Fountain is a large interactive video sculpture. During the summer, the faces on the Crown Fountain pour water from their mouths onto those beneath it.
Time needed: 1-3 hours
Price: Free
How to get there: The Washington/Wabash or State/Lake stations
The Art Institute of Chicago is consistently rated as one of the top museums in the world! The museum is home to over 300,000 pieces of artwork, including one of the largest collections of Impressionist paintings, including artwork by Monet and Vincent Van Gogh.
Time needed: 2-3 hours
Price: $25 for adults, $19 for teens, free for children
How to get there: The Adams/Wabash station
Shedd Aquarium is located on Lake Michigan’s shores and is home to over 1,500 species, including jellyfish, dolphins, sharks, whales, and sea otters. It partners with other organizations around the world to rescue and rehabilitate wildlife and protect endangered species. Shedd Aquarium has a variety of exhibits for anyone looking to experience amazing aquatic life!
Time needed: 4-5 hours
Price: $40 for adults, $30 for children
How to get there: The Roosevelt station
Day 3 in Chicago
The third day of the itinerary has a breathtaking tour, lake views, and a thrilling experience.
The Chicago Architecture River Cruise is one of the top boat tours in North America, bringing you through the Chicago River and providing the history of the architecture. The boat tour is one of the best ways to experience the city and its stunning views. You will not be disappointed in starting your day off with this incredible tour!
Time needed: 1.5 hours
Price: $50
How to get there: The State/Lake station
The Chicago Riverwalk is a 1.25-mile trail that runs along the Chicago River and is perfect for a leisurely walk. You can also rent kayaks to explore the river!
Time needed: 2-3 hours
Price: Free to walk; $30 for kayak rentals
The Navy Pier stretches into Lake Michigan and has a theater, restaurants, shops, a Ferris wheel, and the largest rooftop bar in the world! It is the perfect place to watch fireworks, special events, and the sunset. The Centennial Wheel is one of the most popular attractions on the Navy Pier, soaring over 200 feet in the air with climate-controlled gondolas for riders to take in beautiful views year-round. Another iconic Navy Pier attraction is Offshore. Offshore holds the title with the Guinness World Records for being the largest rooftop bar in the world! It has delicious food, drinks, and incredible views of Lake Michigan and Chicago’s skyline.
Time needed: 1-2 hours
Price: Free to walk the pier; $18 for Centennial Wheel
How to get there: The Grand station
The Willis Tower is the second tallest building in North America, towering over 1,450 feet high, and is a must-have on every Chicago itinerary! The building has 110 floors that are home to over 100 different companies. The SkyDeck is on the 103rd floor and is the reason over a million people from all over the world visit the Willis Tower every year. The Skydeck has glass boxes that extend over four feet out of the building, allowing visitors to feel like they are walking on air over Chicago from 1,353 feet high. The exhilarating experience also provides incredible views of over 40 miles on clear days!
Time needed: 1-2 hours
Price: $26 for adults, $18 for children
How to get there: The Quincy station
Day 4 in Chicago
The final day of your 4 days in Chicago includes a free activity and an iconic ballpark, where you can catch a baseball game!
Lions and tigers and bears, oh my! Lincoln Park Zoo is one of the most established zoos and has one of the largest conservation and science programs in the United States! And it gets better! Lincoln Park Zoo allows visitors to experience hundreds of species for free!
Time needed: 3-4 hours
Price: Free
How to get there: The Clark/Division station
Wrigleyville is a beautiful neighborhood north of Chicago that is home to the iconic Wrigley Field. You can walk around the area while enjoying a drink at a sports bar or delicious food from one of the many restaurants.
Time needed: 1-2 hours
Price: Free
How to get there: The Addison station
Baseball fans cannot plan a trip to Chicago without seeing a game at Wrigley Field. Wrigley Field is the second-oldest active MLB baseball stadium and home to the Chicago White Sox. The stadium is beautiful, with an outfield wall covered in bright green ivy. You can also take a tour if you don’t want to see a baseball game.
Time needed: half day
Price: Varies
How to get there: The Addison station
Chicago 4-Day Itinerary Summary
Day 1:
Magnificent Mile
John Hancock Building
Chicago Theatre
Day 2:
Millennium Park
Art Institute of Chicago
Shedd Aquarium
Day 3:
Chicago Architecture River Cruise
Chicago Riverwalk
Navy Pier
Willis Tower
Day 4:
Lincoln Park Zoo
Wrigleyville
Wrigley Field
If you want to spend 4 days in Chicago, this guide is the perfect place to start planning! It has everything you need to know to create the best Chicago 4-day itinerary. Whether you want to visit art museums, get an adrenaline rush on the Skydeck, or explore a new city, Chicago is a fun city to visit!
Hey, I’m Nichole!
I am the creator behind Nichole the Nomad, the home of my explorations around the world, mountain hikes, and beautiful pictures taken along the way. I have a deep passion for capturing the world in a beautiful light and sharing my experiences.
I created this blog to share my travels, show how beautiful the world is, provide tips and tricks for traveling, and encourage you to explore. Whether you want to travel across the world or explore what’s in your backyard, I hope this blog inspires you to get outside and find your adventure!
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