Chicago is hands down one of my favorite cities on Earth. It has delicious food, towering skyscrapers (I mean, that skyline!), world class museums and a bustling nightlife. All of which make the Windy City a top holiday destination. It’s a fabulous destination for families, both foreign and domestic alike, due to the amazing Lincoln Park Zoo and Shedd Aquarium. If you’re young and looking for a fun weekend warrior trip, hit a Cubs game and bar hop around Wrigleyville. Whatever you fancy, there is something in Chicago for every traveler.
Simple City Guide to Chicago: The Windy City Edition
What Chicago airport should I choose?
Fly into Chicago Midway and avoid O’Hare International if possible. I mean, have you seen Home Alone? O’Hare is a huge airport, further away from the city and has a history of delayed flights. Midway on the other hand, is smaller, closer to the city and has notoriously shorter security lines. The only caveat to Chicago Midway is that not as many airlines fly into there, so be sure to choose airlines such as Southwest .
Where should I stay in Chicago?
A hotel along Magnificent Mile or The Loop makes for a great home base while in Chicago. Being along Mag Mile will offer a close proximity to great shopping, restaurants, Millennium Park, Lake Michigan and Navy Pier. Great options along Mag Mile are: Chicago Marriott Magnificent Mile and Double Tree MagMile. The Loop makes for a great option if you want to explore the city by train while still staying in close proximity to all the highlights. Great hotel options within the Loop are Hilton Palmer House and The Waldorf Astoria.
Free things to do in Chicago…
One of the things that I love most about Chicago is the abundance of fun and free things to do. Below is my list of amazing free things to do in the Windy City.
- Lincoln Park Zoo
- Millenium Park
- Magnificent Mile
- Checking out Chicago River Walk
- Navy Pier
- Beach Day at Lake Michigan
- Lakefront Trail
- Chicago Cultural Center
- Lincoln Park Conservatory
Where to party in Chicago?
Bar hop in Wrigleyville. Enjoy a cocktail from a Chicago rooftop bar. Or get secretive and go to a speakeasy for fun libations.
What else should I do in Chicago?
There is so much to do in Chicago. If you’re a sports buff, check out a Cub’s game at the historic Wrigley Field. If you want to be like Ferris Bueller, grab your friends or a loved one and check out the sites from Willis (formerly Sears) Tower. Below are additional ideas of fun things to add to your city guide to Chicago.
- Chicago River Cruise
- Rent bikes and ride along the Lakeshore.
- Check out Shedd Aquarium.
- Go to the top of Hancock Tower for drinks at Chicago 360.
- Admire beautiful art pieces at the Art Institute of Chicago.
- Listen to live jazz at various bars and music halls.
- Catch a show at the legendary Chicago Theatre.
- Visit the Museum of Science and Industry.
What should I eat while in Chicago?
I know what I am about to put is going to be found in any city guide to Chicago, but there is a reason for it. These foods are damn good. Here are my top (and very touristy) choices for what to eat in Chicago.
- Chicago-style Hot Dogs: Beef frank in poppyseed bun with all the fixings. DO NOT GET KETCUP. It’s insulting. Try Jim’s Original
- Chicago-style Deep Dish pizza. Oh Lord. We ate at various establishments and honestly cannot get enough. Go ahead and get down with your bad self with the meat lover. Locals and travelers all have their personal favorites, from Lou Malnatis to Pequod’s Pizza
- Eat at a fancy steakhouse. There is something about a classy sub-basement steakhouse that makes me feel like I could be in a scene from Boardwalk Empire. Try Bavette’s Bar and Boeuf.
- Get popcorn. Sounds random, but Chicago is famous for their popcorn. Grab some from a Garrett Popcorn Shop.
I hope you liked my quick and simple city guide to Chicago, the Windy City edition. If you have any other additional questions about what to do, when to go, or even what to wear, feel free to reach out to me: chloe (at) timetravelblonde.com. I hope you have a fabulous day and thank you again for stopping by!