How to Spend a Day in Chicago | The Ultimate Guide

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Last Updated on November 23, 2024 by sydabroad

If you are planning to spend a day in Chicago, keep reading! 

Chicago (in the summer) is one of my favorite cities in America. It’s a lively city known for its historic architecture, vibrant culture, art, and food scene. In this guide, we’re diving into the perfect 1 day in Chicago itinerary.

Keep reading to discover the best things to do in Chicago, where to eat, how to get around the city, and more! Whether you are staying in Chicago for the day or a weekend, this guide is for you. I’ve also included a map later in this guide with all the spots mentioned, so save this post for your trip. 

Looking for more USA guides? 

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This article is all about how to spend a day in Chicago, Illinois. 

A Day in Chicago | The Best Things to Do in Chicago, Illinois 

We’re diving into the best way to spend a day in Chicago! Although a day is not nearly enough time to cover all that this city has to offer, you can see a lot. Make sure you pack comfy shoes and prepare for a busy day! 

Coffee! 

Begin your one day in Chicago with coffee! There are plenty of amazing cafes and coffee shops around the city. A few of my favorites are Blue Bottle, Starbucks Reserve, and Herb & Alchemy Coffee Shop.

Visit Millennium Park | The Bean

You can’t visit Chicago without seeing The Bean. The Bean is properly known as Cloud Gate which is situated in Millennium Park. Take your selfies in The Bean and explore the park’s gorgeous gardens and the Crown Fountain. 

I suggest visiting early in the day because this is obviously a popular tourist spot in Chicago. If you want photos with fewer people, visit in the morning. 

Magnificent Mile 

While you are exploring Millennium Park, stroll down Magnificient Mile for sightseeing and shopping. This is Chicago’s premier commercial district. It’s a busy area with upscale shops, plenty of restaurants, and boutique hotels. 

Architecture Boat Tour 

One of the best things to do in Chicago is to take an architecture tour. You can book a guided architecture cruise here. This is the best way to experience the city’s legendary architectural history and iconic buildings. 

Cruise down the Chicago River while learning all about the city’s fascinating architecture. I suggest booking your tickets in advance, especially if you visit during the summer months. I have a guide here all about the best boat tours in Chicago, so check it out if you plan on visiting!

Book a Chicago Architecture tour here

Chicago Style Pizza for Lunch

Chicago is renowned for its deep-dish pizza – a must-try dish while visiting the city! It’s very different than the traditional NYC-style pizza. 

Chicago’s deep dish pizzas typically have the cheese and the toppings on the bottom instead of the top. And you can also find traditional stuffed pizza. I suggest visiting Giordano’s! I ate here during my first trip to Chicago and it was incredible!

If you want to sightsee around Chicago without all the walking, consider booking the Hop-on Hop-off bus!

City Bike Around the City

What better way to explore the city than by bike? You’ll find bikes all around the city and can unlock a bike using the Divvy app. The Chicago Riverwalk and the Lakefront Trail are great places to ride for stunning views of Lake Michigan, landmarks, public art, beaches, and parks. 

Optional: Starbucks Reserve

If you are looking for an afternoon pick-me-up, head to the Starbucks Reserve. I don’t normally recommend visiting a Starbucks when traveling however, the Starbucks Reserve in Chicago is quite the experience. 

This is the largest Starbucks in the world, offering 5 floors each with a unique experience. You can find an array of food and drink options – much more than at a typical Starbucks.

The first floor is the Main Bar, the second floor is the Princi Bakery and Cafe, then you’ll find the experiential coffee bar on the third floor, and the Arriviamo Bar on the fourth floor. Finally, on the fifth floor, you’ll get to experience the Rooftop Terrace. 

Pro-tip: If you are visiting during the fall, you HAVE to try the pumpkin spice espresso martini. They are to die for. Best espresso martini ever.

LondonHouse for Drinks 

For pre-dinner cocktails, head to LondonHouse. This is one of the most famous rooftop bars in Chicago, offering stunning views of the city and the Chicago River. You’ll find craft cocktails, fine wines, and small plates. The ambiance is incredible, you can’t miss LondonHouse when you visit Chicago! 

Dinner in Chicago

There is certainly no shortage of amazing dinner spots in Chicago. But a couple of my favorites are Gibsons Italia and Bar Mar by José Andrés. 

If you are looking for Italian, head to Gisbons Italian. Not only is the ambiance incredible, but this is seriously one of the best Italian restaurants I have ever visited. The food was 10/10. 

Alternatively, if you are looking for seafood in Chicago, I recommend Bar Mar. Again, this was absolutely delicious. They offer wonderful seafood dishes and amazing cocktails. I love both of these restaurants in Chicago. 

Chicago Theater District 

How to end a day in Chicago? Visit the iconic Chicago theater district! The theater district is located in the heart of downtown Chicago known for its Broadway productions and diverse entertainment options. 

It’s a great way to spend an evening in Chicago. Book your tickets in advance if you plan to see a performance. 

Additional Things to Do in The City 

Are you staying a bit longer in Chicago and looking for more fun things to do? Here are a few recommendations! Of course, you can’t see the entire city of Chicago in just one day, but you can squeeze in a lot. Here are some other amazing things to do in the city!

Art Institute of Chicago | This is one of the oldest and largest art museums in the United States. At the Art Institute of Chicago, you’ll find a vast collection of artwork from all around the world spanning thousands of years. 

Food Tour in Chicago | Chicago has a vibrant food scene. Experience the culinary delights of this city by booking a food tour! You can book a Chicago food tour here. 

Grant Park | This is a large urban park in the Loop area of Chicago. It’s a highlight of the city, much like Central Park in New York City. 

Wrigley Field | If you have extra time in Chicago, catch a Cubs baseball game at Wrigley Field! 

Navy Pier | Navy Pier is one of Chicago’s most popular spots to visit. It offers a wide range of entertainment, dining, and attractions along Lake Michigan. 

Skydeck Chicago | Looking for panoramic views of the city? Head to Willis Tower Skydeck. On the 103rd floor of the Willis Tower, you’ll find the highest observation deck in the United States. Book your tickets in advance here.

FAQs About a Day in Chicago

How to Get to Chicago? 

If you aren’t driving to Chicago, you can travel to Chicago via the city’s public transportation line, or fly into either Chicago O’Hare International Airport or Chicago Midway International Airport. 

What is The Best Way to Get Around Chicago? 

Chicago has an extensive public transportation system. The Chicago Transit Authority (CTA) consists of Trains (the “L” train system) and buses. 

Alternatively, you can also walk, bike, and use ride-share apps such as Uber and Lyft. Chicago is a pedestrian-friendly city and there are plenty of ways to get around. 

Is One Day Enough for Chicago? 

You can see a lot of the city in one day, however, you can’t see it all. There is so much to experience in Chicago, you’ll need at least a weekend to experience all that the city has to offer. 

Is Chicago Worth Visiting? 

Yes! This city needs to be on your bucket list. I do suggest visiting in the summer or spring because it’s cold during the wintertime. But Chicago in the summer is seriously the best. 

What is The Best Way to Tour Downtown Chicago?

The best way to see downtown Chicago in my opinion is either by walking or by a river cruise tour. Both are wonderful ways to experience downtown Chicago. You can book walking tours and river cruises here.  

The Weather in Chicago 

The weather in Chicago can be a bit rough. In the winter is cold and windy. However, in the summer it’s typically warm in sunny. I honestly recommend avoiding Chicago in the winter, especially if you want to spend a lot of your time outside.

Also if you visit in the summer, you can enjoy spending time on Lake Michigan. You can rent jet skis, and boats, or relax on the beaches. 

Where to Stay in Chicago 

Search for hotels in Chicago here. 

Map

I hope you enjoyed this guide all about how to spend a day in Chicago! This is a wonderful city with so much to enjoy. If you have any questions about planning your trip to Chicago, DM me on Instagram or comment below!

Recommended Tours in Chicago

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