Perfect Chicago 2-Day Itinerary Exploring the City
Chicago is an incredible city with stunning architecture, delicious deep-dish pizza, and a beautiful lake. Since it is among the largest cities in the United States, you could spend an entire week exploring everything Chicago offers. But you can create an incredible Chicago 2-day itinerary that explores many of the must-see attractions.
We spent a weekend exploring Chicago, and it was the perfect amount of time to see everything on our Chicago itinerary! This guide has everything you need to know to plan a trip to Chicago, including the best things to add to an epic Chicago 2-day itinerary.
Fun facts about Chicago:
Chicago is the third-largest city in the United States.
Chicago’s Home Insurance Building was the first skyscraper in the world, standing only ten stories tall.
The Chicago River is the only river in the world that flows backward. It flows backward to prevent sewage from flowing into Lake Michigan.
Chicago is home to one of the largest food festivals in the world. The Taste of Chicago is a five-day event where millions of people visit to eat delicious food and enjoy a variety of musical performances.
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Tips for Creating a Chicago 2-Day Itinerary
Use Chicago's transit system because it is easy to use and can take you everywhere you need to go on your itinerary. You can purchase a one-day, three-day, or seven-day Ventra Cards for your trip. I recommend buying a multi-day ticket once you get into the city, so you can easily use the transit system.
Get discount cards for the attractions you want to see. Your trip to Chicago does not have to be expensive. There are many ways to save money, including 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 for your trip. When you plan a trip to Chicago, it's important to know that the weather can be unpredictable, and Lake Michigan can create drastic temperature changes and high winds. If you are visiting in the warmer months, I recommend bringing a rain jacket. In the winter months, I recommend packing many layers as it can be very cold, including an insulated jacket.
Pack comfortable shoes for walking around Chicago. This Chicago 2-day itinerary will include a lot of walking, so it is important to have comfortable and supportive shoes. I always recommend wearing running sneakers because they provide great support and comfy socks.
Best Time to Visit Chicago
Winter is one of the most underrated times to visit Chicago. If you are okay with cold weather and snowy streets, you will love this quiet time to visit. You can enjoy walking down snowy streets and spending your days staying warm in museums, art exhibits, and restaurants!
Spring in Chicago is beautiful once the snow melts and everything blooms. The only downside to spring is it tends to rain a lot and be very windy. If you are okay with some wind and rain, you will not be disappointed visiting in the spring!
Summer is one of the most popular times to visit Chicago because the weather is warm, and all tours and facilities are open. You can enjoy walking along the Chicago River and Lake Michigan in the gorgeous summer weather and sitting outside to eat. We love visiting Chicago in the summer because the weather is gorgeous!
Fall is one of the most beautiful times to visit Chicago because the weather is perfect, and there is foliage! Although the city has fewer trees than other areas, you can still find beautiful foliage!
Closest Airports to Chicago
When you plan a trip to Chicago, there are two airports you can fly to 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.
We have flown into both airports since they both have many flight options from major airports. Both are the closest airports to Chicago and link with its transit system, making it easy to get to and from the airport.
How to Get Around Chicago
Walk: Chicago is walkable, so I always recommend walking through the city as a way to get around. Walking is also free! I think walking is the best way to enjoy the city and its stunning views.
CTA: The CTA is a cheap and great way to explore the city. Chicago’s transit system can be confusing, but you can use Google Maps to understand where a stop is and where the line will bring you. I found the CTA easy to use during our stay in Chicago!
Divvy Bikes: Divvy Bikes has thousands of bikes around Chicago, so you can pick up and drop off bikes wherever needed!
Uber/Lyft: Uber/Lyft are great options for getting around without worrying about parking.
Car rental: I do not recommend renting a car. Although it is doable, traffic and finding parking in Chicago can be a nightmare.
Best Places to Stay in Chicago
Chicago is a large city with many neighborhoods, and I can help you find the best area to stay in Chicago! When you plan a Chicago 2-day itinerary, 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.
The Loop/Downtown Chicago
The Loop/Downtown Chicago is the most well-known area in Chicago because it is near many must-see sights. Some of the best hotels are:River North
River North is true to its name because it is located north of the Chicago River. It is still very close to downtown Chicago and is home to many art galleries. Some of the best hotels are:Streeterville
Streeterville is north of River North and near the famous Magnificent Mile and Navy Pier. Some of the best hotels are:Gold Coast
Gold Coast is located along Lake Michigan and is the most high-end neighborhood in Chicago. Staying in this Chicago neighborhood will be more expensive than staying in the others mentioned. Some of the best hotels are:Best Restaurants in Chicago
When you plan a trip to Chicago, make sure to try the delicious food the city offers! Chicago has so many incredible places to eat, so you really cannot go wrong with any restaurant you choose. BUT at some point in your trip, you have to eat deep-dish pizza. Some people say it is overrated, but I beg to differ!
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 - oldest Italian restaurant in Chicago with delicious food
The Purple Pig - an overall delicious restaurant
BomboBar - amazing desserts
Chicago 2-Day Itinerary Overview
Below is a quick overview of this fun Chicago itinerary before we dive into the details of each attraction!
Day 1:
Millennium Park
Art Institute of Chicago
Shedd Aquarium
Willis Tower
Chicago Riverwalk
Navy Pier
Chicago Theatre
Day 2:
Chicago Architecture River Cruise
Magnificent Mile
John Hancock Building
Lincoln Park Zoo
Wrigley Field
The Best Chicago 2-Day Itinerary
This Chicago 2-day itinerary has something for everyone, no matter how you want to experience the city, including art museums, architecture tours, sports events, theaters, and zoos. When we visited, we had plenty of time during our two days to see everything on our Chicago itinerary.
Chicago has an incredible transit system that is easy to use and brings you anywhere you need in Chicago, including the airport. Chicago is also easy to navigate if you prefer to walk! When you plan a trip to Chicago, I recommend purchasing tickets to the must-see attractions ahead of time!
Pro tip: Purchase the Chicago CityPASS if you are looking to see the highlights of Chicago. The pass provides admission to many of the must-see attractions.
Day 1 in chicago
The first day of this Chicago 2-day itinerary has many iconic attractions in Chicago south of the Chicago River! We loved visiting these iconic places in Chicago, so I know you will too.
Millennium Park
You cannot plan a trip to Chicago without including Millennium Park in your itinerary! Millennium Park is located on the lakefront in downtown Chicago and has beautiful art throughout the campus, including the iconic Cloud Gate statue. It was one of our favorite places in Chicago!
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
How to get there: The Washington/Wabash or State/Lake stations
Art Institude of Chicago
The Art Institute of Chicago is consistently rated as one of the top museums in the world and is a must-see when visiting Chicago. 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.
Everyone will enjoy taking the time to explore the beautiful exhibitions at the Art Institute of Chicago! I am not a huge art person, but I loved visiting the Art Institute of Chicago!
Time needed: 2-3 hours
How to get there: The Adams/Wabash station
Shedd Aquarium
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!
We love visiting the Shedd Aquarium because it is huge! It is also in a beautiful part of Chicago, making it a great place to visit.
Time needed: 4-5 hours
How to get there: The Roosevelt station
Willis Tower
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.
We love visiting the Skydeck, and we go every time we are in Chicago. The views are incredible, overlooking the entire city. The exhilarating experience also provides incredible views of over 40 miles on clear days!
Time needed: 1-2 hours
How to get there: The Quincy station
Chicago Riverwalk
Are you looking to enjoy a leisurely walk along the water? The Chicago Riverwalk is a 1.25-mile trail that runs along the Chicago River and offers opportunities to get out on the water.
There are a variety of sightseeing cruises and kayak rentals. I highly recommend exploring the Chicago River on a kayak! The Chicago Riverwalk is also a great way to walk from the Willis Tower to the Navy Pier. We always love enjoying a walk here because of its breathtaking city views.
Time needed: 2-3 hours
Navy Pier
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 easily one of our favorite places to visit in Chicago, and it is a perfect place to watch fireworks, special events, and the sunset.
The Centennial Wheel is one of my favorite 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. It is a fun way to enjoy the city skyline.
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 and drinks and offers incredible views of Lake Michigan and Chicago’s skyline.
Time needed: 1-2 hours
How to get there: The Grand station
Chicago Theater
The Chicago Theater is an iconic landmark in Chicago, offering a variety of Broadway shows, concerts, and musicals, and is the perfect way to end the first day of this Chicago 2-day itinerary.
It is known as the unofficial symbol of the city and is featured in many famous movies, television shows, and photographs. I highly recommend seeing a show at the Chicago Theater!
Time needed: Varies by the show
How to get there: The State/Lake station
Day 2 in chicago
The second and last day on this incredible Chicago 2-day itinerary has a breathtaking tour, fun events, and city views. You can add as many things to the last day of this itinerary, depending on when you leave the city!
Chicago Architecture River Cruise
It is time to start your day with a breathtaking architecture boat tour. 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 city’s architecture.
The boat tour is one of the best ways to experience the city and take in the stunning views. It is our favorite thing to do when we are in Chicago, so I know you will not be disappointed in starting your day off with this incredible tour.
Time needed: 1.5 hours
How to get there: The State/Lake station
Magnificent Mile
The Magnificent Mile is an iconic street in downtown Chicago with everything from restaurants, luxury stores, upscale shops, and more. It is our favorite place to walk and shop. It also has the John Hancock Building, which is the next attraction in this Chicago 2-day itinerary.
Time needed: 1-2 hours
How to get there: The State/Lake station
John Hancock Building
If you are looking for another thrill after experiencing the Skydeck, the 360 Chicago Observation Deck is the perfect addition to your itinerary. We love the city views from the top!
Located on the top of the John Hancock Building, the 360 Chicago Observation Deck 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!
Time needed: 1-2 hours
How to get there: The Chicago station
Lincoln Park Zoo
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.
We visited the Lincoln Park Zoo the first time we visited Chicago. It was a beautiful walk from downtown and a fun experience.
Time needed: 3-4 hours
How to get there: The Clark/Division station
Wrigley Field
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 is home to the Chicago White Sox.
The stadium is beautiful, with an outfield wall covered in bright green ivy. If you are a baseball fan, seeing a baseball game at Wrigley Field is a must! I loved my time at a Chicago White Sox game!
Time needed: half day
How to get there: The Addison station
Are you ready to plan a trip to Chicago? This guide is the perfect place to start to create the best Chicago 2-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 for a weekend getaway!
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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