Weekend in Chicago: What to Do & How To Do

Chicago is a vibrant and bustling city that has something for everyone. Whether you’re interested in world-class museums, stunning architecture, delicious food, or lively nightlife, you won’t be disappointed.

“I love Chicago. It’s the pulse of America.”

— Paula Danziger

If you’re planning to spend a weekend in Chicago, there are plenty of things to do and see that will help you make the most of your trip. In this guide, we’ll recommend the best things to do in Chicago as a tourist, so you can have an unforgettable weekend in the Windy City.

Friday Evening

Start your weekend off by taking a stroll down the Magnificent Mile, one of Chicago’s most iconic shopping destinations.

Here you can find everything from high-end designer boutiques to affordable chain stores. Once you’ve worked up an appetite, head over to Lou Malnati’s Pizzeria for a taste of Chicago’s famous deep-dish pizza.

Saturday Morning

Start your day off with a visit to Millennium Park, home to the famous Cloud Gate sculpture (aka “The Bean”).

Take a selfie with the shiny silver sculpture and then head over to nearby Buckingham Fountain for a beautiful view of the city skyline.

Next, head over to the Art Institute of Chicago to explore some of the world’s most famous art collections.

Saturday Afternoon

Take a break from the hustle and bustle of the city by visiting Lincoln Park, a beautiful green space that’s home to a zoo, conservatory, and several museums.

If you’re feeling adventurous, rent a bike and ride along the lakefront trail for stunning views of Lake Michigan.

Saturday Evening

For dinner, head over to the West Loop, one of Chicago’s trendiest neighborhoods, for a variety of dining options.

Try the famous Au Cheval burger or enjoy some Spanish-style tapas at Bar Ramone.

After dinner, catch a show at the iconic Second City Comedy Club, where famous comedians like Tina Fey and Stephen Colbert got their start.

Sunday Morning

Start your day with a visit to the Navy Pier, a popular destination that offers stunning views of Lake Michigan and the city skyline.

Here you can ride the Ferris wheel, take a boat tour, or explore the many restaurants and shops.

If you’re interested in architecture, take a riverboat tour to see the city’s famous buildings from a new perspective.

Sunday Afternoon

Spend your last afternoon in Chicago by visiting the Museum of Science and Industry, one of the largest science museums in the world.

Here you can explore exhibits on everything from space exploration to the human body.

If you have time, take a walk through the nearby Hyde Park neighborhood, which is home to the beautiful University of Chicago campus.

Chicago Car Parking for Weekend

Finding parking in Chicago can be challenging, but there are several options available for weekend parking.

Street parking is available in many neighborhoods throughout the city, but be sure to check for any parking restrictions. Public parking garages are also plentiful and can offer discounted rates on weekends.

If you’re staying in a hotel, check to see if they offer parking for their guests. Alternatively, you can park at a suburban train station and take public transportation into the city. Finally, parking apps like ParkWhiz and ParkChicago can help you find and reserve parking spots in advance, often at discounted rates. With some planning and research, you can find affordable and convenient parking options for your weekend in Chicago.

Chicago Free Co-Working Spaces

If you’re looking for free coworking spaces in Chicago, there are several options available.

The Chicago Public Library offers free coworking spaces in several of its locations, including private study rooms and collaborative workspaces.

Additionally, some cafes and coffee shops, like Filter Cafe and Intelligentsia Coffee, offer free coworking spaces during certain hours.

Another option is to join a coworking community, like 1871 or Blue Lacuna, which offer free coworking days and events for members. With a bit of research and exploration, it’s possible to find free coworking spaces in Chicago that meet your needs and budget.

Chicago Eating and Drinking Places

Chicago is a foodie’s paradise, offering a diverse range of cuisines and dining experiences. For classic Chicago-style deep-dish pizza, head to Giordano’s or Lou Malnati’s.

For upscale dining, try Alinea or Girl & the Goat. For more affordable eats, visit Portillo’s for Chicago-style hot dogs and Italian beef sandwiches or the iconic Billy Goat Tavern for a cheeseburger and a beer.

Chicago also has a thriving craft beer scene, with breweries like Half Acre Beer Company and Revolution Brewing serving up delicious and unique brews. Whether you’re looking for fine dining or casual eats, Chicago has something to offer every palate and budget.

Chicago is beautiful travel destination and city that never sleeps, and with so much to see and do, it’s easy to see why. By following this weekend guide, you can experience some of the best things that Chicago has to offer, from iconic landmarks to delicious food to world-class museums. So pack your bags and get ready for an unforgettable weekend in the Windy City.