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First-Timers Guide to Chicago

Chicago is one of my favorite cities to visit. Here are a couple of must-see places, especially if you are a first-timer.

Architecture River Cruise

The Architecture River Cruise is an absolute must to see the best of Chicago while learning about its history. We also used the time on the boat to scope out some restaurants we wanted to check out along the water. The tour is very informative and goes by quick. I recommend getting tickets ahead of time because times sell out.

Willis Tower

This is an iconic building that offers a great and unique view of Chicago. The Willis Tower is the second-highest building in the US next to the World Trade Center. The observation deck allows you to step over a clear glass that can be intimidating if you are afraid of heights. As always with popular tourists locations, I recommend getting to the Willis Tower early in the morning.

River Walk

Walk along the River Walk. This is an area where you can people watch, go for a stroll or enjoy a bite/drink. You get to see boats go by and get a different vibe of the city.

Cubs Game – Wrigley Field

We went to a Cubs game the first time we were in Chicago. I am not a sports fan but I can definitely appreciate the history of Wrigley Field and the Cubs. The game we saw was very exciting. We watched a couple of slides that were made by a hair. They had to replay them a couple of times to figure out if the player was safe or not.

You can also check out the restaurants and bars around the area. I wouldn’t say a particular one stood out but you can grab a drink or two before the game. It’s funny to see people going into houses close to the stadium as if there were going to the game but really they are just going to sit on their friend’s rooftop to see the game. Since the stadium has gaps where neighbors can peek in to see the game from a distance.

Navy Pier

The Navy Pier has a variety of things you can enjoy. There is the Navy Pier Pier Park with Ferris Wheel, Children’s Museum, Beer Garden, and small shopping area. This is a great area to go for a walk by the water with a variety of things to do depending on your interested. There are also, cruises available.

Children’s Museum

Chicago’s Children Museum is a great option if you have little ones. They have various activities depending on age. Open Playground in Pritzker Playspace is for babies and toddlers only. This area has a lot of room and activities for crawlers and little walkers to explore (no shoes allowed). Younger kids can also enjoy “kids town,” which features cash registers, carts, artificial food, crawling area. There is an area where kids can go on a dinosaur expedition, explore camping/outdoor experience, waterways, just to name a few. For the older kids, there’s a “tinker lab” where they can use saws, hammers, and other tools to build projects. All ages are offered different workshops to participate. They can even learn to make sushi!

Michigan Avenue

Complete your trip by shopping until you drop! There are so many stores to choose from. Whether you are looking for high-end or affordable you will find it here. They can it Magnificant Mile for a reason! If you are a kid at heart, check out Dylan’s Candy Bar.

Dylan’s Candy Bar

Millennium Park

Finally Millennium Park! Not only is Cloud Gate here “the bean” but there are also other things the park has to offer. Millennium Park has outdoor workouts, concerts, art, gardens, live jazz, and theatre performances. Check out the events calendar on their site.

Buckingham Fountain

Grant Park features Buckingham Fountain, one of the largest fountains in the world. The fountain is worth the walk. It’s a unique 3-level rococo fountain that offers light & water shows. Note: This area is a 15-minute walk from Millennium Park.

Chicago Restaurants

Chicago has a great mixture of cuisine to check out. Not only is the food amazing but you can also enjoy a nice view and vibe. I have put together my Top 10 Chicago Food Spots.

Here are other fun vacations to check out:

Do you have any recommendations for things to do in Chicago?

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