Chicago Travel Guide

Chicago is one of the most iconic cities in the US and it is easy to see why with its miles of sparkling sky scrapers, rich history, & pristine location along Lake Michigan. Escaping the heat in Cincinnati for a 3-day weekend in Chicago, we heading north to explore the windy city. This Chicago travel guide highlights where to stay, what to pack, & the top 10 things to see in the city …

Disclaimer: This post contains affiliate advertising, which means that if you click on or purchase a product through a link, I may earn a commission. 

Chicago Travel Guide

What to Pack for Chicago

Chicago can be hot in the summer! I like to pack organic cotton shirts that are super light weight (such as this amazing Everlane Crewneck Tee) and fun dresses that I can wear during the day or at night for dinner (such as this Club Monaco dress). We tend to walk around the city so having comfortable shoes are ideal, such as these Cole Haan Grand Crosscourt Slip-On Sneaker. Also, every time we go to Chicago it tends to rain so I always pack a rain jacket. This Cole Haan Travel Packable Rain Jacket is ideal and packs into a tiny pocket that slips easily into my purse.

Where to Stay

Every time we go to Chicago, we always stay at the Palmer House – Hilton Hotel. One of the most historic hotels in all of Chicago, it feels decadent the moment you walk in. From lavish grand staircases to golden decorated parlors, the hotel feels like you stepped back into the roaring 20s. Plus it is within walking distance to all our favorite things from Millennium Park, to amazing restaurants, and of course the Magnificent Mile.

What to Do in Chicago

As part of this Chicago travel guide, these are the top 10 things to not miss in the city:

1 | Cloud Gate – AKA ‘The Bean’

A short walk away from the Palmer House is Cloud Gate (free). Located in Millennium Park, ‘The Bean’ sculpture reflects the stunning Chicago skyline. Seeing ‘The Bean’ and taking photos around and under has become iconic for the windy city.

2 | Millennium Park

Millennium Park has much more to explore besides Cloud Gate. This expansive park takes up multiple city blocks and is a perfect way to spend an afternoon. Whether it’s grabbing a bite to eat from one of the many food trucks or exploring the gardens throughout, there is something for everyone at the park.

3 | Willis Tower

The Chicago Skyline has countless famous buildings, but none is more famous than Willis Tower (tickets are ~$25). This tower stands over 1,450 feet high, making it one of tallest buildings in the world. The observation deck on floor 103 is a great way to see the entire city. They are famous for having clear glass rooms where you can see the cars below your feet as you stand over the tower’s ledge.

4 | Boat Cruise

Another great way to see the city is on one of the many great boat cruises throughout the city. One of my favorite is the Wendella Architecture Boat Tour (tickets are ~$39) that takes you through the inner city rivers to see the amazing buildings throughout the city and water front. It’s a great way to see the city from a different perspective while also learning more about the amazing architecture of the city. Make sure to bring a light sweatshirt (such as this fun stripped one from J.Crew) or a rain jacket (such as my favorite Cole Haan Packable Rain Jacket) to block the wind while on the water.

5 | Navy Pier

Another great place to go in Chicago is Navy Pier. From the Children’s museum to the amusement park to just walking along the pier, this pier has tons of fun things to do for all ages (and most are free or inexpensive).

6 | The Art Institute of Chicago

Another one of my favorite things to do in Chicago is visiting the Art Institute (~$25 for an adult ticket). Located only a short walk away from the Palmer House and Millennium Park, the Art Institute holds some of the finest works of art including works by Suerat, Manet, Monet, Van Gogh, Picasso. My favorite exhibit is the expansive America Windows by Chagall.

7 | Hancock Tower

Not only does the Willis Tower offer amazing views of the city, but the Hancock Tower does as well (tickets are ~$25). They have an observation deck, but they also have a restaurant where you can enjoy the some of the best views of the city over drinks and food.

8 | The Field Museum

Another don’t miss in Chicago is the Field Museum (tickets are ~$40 for adults). This expansive museum covers everything from the dinosaurs (with numerous complete skeletons on display) to ancient Egypt to sparkling gems and jewels.

9 | Shedd Aquarium

The Shedd Aquarium is one of the best in the country (tickets are ~$40). The expansive exhibits range from colorful coral reefs across the world to dolphins, belugas and sea otters.

10 | Magnificent Mile Window Shopping

Last but not least, you can’t miss strolling down the Magnificent Mile for some shopping. Covering the distance north along Michigan Avenue, this premier shopping area has trendy high end boutiques that are perfect for window shopping and browsing. Make sure you don’t miss the amazing Ralph Lauren store for some great preppy fashion ideas (like this amazing Gingham Dress)!

You might also enjoy: 3-Day Chicago Itinerary and Day 3 in Chicago