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A Weekend Itinerary: Chicago Edition

Updated: May 2, 2020

The Beach and Cloud Gate in Millennium Park overlooking Downtown Chicago
The Bean / Cloud Gate in Millenium Park

Chicago- have you bean there before? (This pun seriously never gets old.) If you haven't, you need to book your next flight now! The Windy City is one of those places you need to visit at least once in your life. With its ample art displays, impressive architecture, and delicious food, you will easily find yourself wanting to extend your stay. If you only have a weekend to spare, don't fret- read along for the perfect weekend itinerary.

Breakfast at Wildberry Pancakes and Cafe in Chicago
Breakfast at Wildberry Pancakes and Cafe

Where to stay in Chicago

I recommend staying at an Airbnb if you are looking for a more affordable accommodation. There are an abundance of homes and apartments that are nearby main attractions. If you're looking for a not-so-cheap option, there are a ton of hotels in and around downtown Chicago as well.

Getting around in Chicago

Chicago is a walkable city, and easily accessible by train, bus, or ride share services. Smart Destinations provides a detailed guide on getting around in the city. I recommend walking between popular spots in downtown and especially along the Chicago Riverwalk, so you're able to discover sights you may otherwise miss.

Day 1

1. Wildberry Pancakes and Cafe: Start your morning off with breakfast at this popular spot. Wildberry Cafe serves huge portions, giving you the energy you need for the day's adventures.

2. Millennium Park: You can easily spend an entire day at Millennium Park. It is filled with expansive green spaces, cool art displays, and even an interactive fountain. Get the perfect photo at Cloud Gate, popularly known as The Bean. Don't forget to go under The Bean and capture fun photos with your friends in its reflection! Want to feel like a kid again? Check out Crown Fountain, which contains two glass towers that project images of Chicago citizens.

3. Magnificent Mile: Magnificent Mile is an upscale shopping destination that stretches along Michigan Avenue. This is the best area to shop, eat, and admire some of the city's tallest buildings.

Millennium Park overlooking Downtown Chicago
Millennium Park

Day 2

1. Art Institute of Chicago: Honestly, I'm not a museum fanatic, but places like the Art Institute of Chicago, the Louvre, and the Met amaze me because of their massive art exhibits. Chicago's Art Institute is one of the top museums in the U.S., and for good reason. It offers a vast variety of art from different cultures and various time periods. You cannot finish the museum in an entire day, so choose your exhibits wisely.

2. Skydeck Chicago: Want some of the best views in the city? Check out the Skydeck at Willis Tower. Its 103rd floor glass viewing platform will not only make a great photo op, but will also help you conquer your fear of heights- or not.

3. Lou Malnati's Pizzeria: A trip to Chicago isn't complete without trying deep dish pizza. Lou Malnati's serves classic Chicago-style pizza- thick, buttery crust and warm, gooey cheese.

Skydeck at Willis Tower in Downtown Chicago sitting on glass platform
Skydeck at Wills Tower

Day 3

1. Yolk: This is another popular spot for breakfast in the city. It was pretty busy on a Sunday morning, so I recommend coming early if you want to get seated quickly. Yolk offers generous portions and a large variety of dishes to choose from.

2. Lincoln Park Conservatory: Lincoln Park Conservatory is a lovely and quiet place to get away from the the bustling city. (And it's free!) It contains multiple rooms housing a variety of beautiful plants, and is the perfect place to relax for an hour or two.

3. Chicago Riverwalk: Take a boat tour or walk along the Riverwalk- I recommend the latter. Walking along the river provides unhindered views of the city's skyscrapers and boats sitting on the riverfront.

4. Eataly: Finish your day with an Italian dinner at Eataly. Eataly is a fun place to check out as it offers numerous Italian eateries and a large marketplace. Eat, drink wine, try new desserts, and hang out with friends here!

Flowers and plants at Lincoln Park Conservatory in Chicago
Lincoln Park Conservatory


1. Visit in late spring or early fall: These are the best times to visit the city. The weather is more bearable than it is during summer, and the crowds won't be as busy.

2. If you're on a budget, purchase the Chicago CityPASS: This is a discounted, prepaid booklet of tickets that gives you access to some of the city's main attractions. Click here for more information.

3. Don't rent a car: It's unnecessary and a hassle to rent a car in the city. As I mentioned, the city is easily accessible by multiple modes of transportation. Walk, take public transportation, or use popular ride share services.

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