5 Day Series: Chicago

Chicago can be easily explored by foot, bike, or with public transportation. The key in planning your stay is the location of your accommodation. The city is exceptionally diverse with so many different cultural influences that there is always something for everyone! While there is so much to do, this list comprises my favorites as a local for a visit in 5 days or less.

Sites & Suggestions

Chicago Architecture Tour

https://www.wendellaboats.com/

The 90 minute River & Lake tour for $39 from Wendella is the best, but you should purchase your tickets in advance as seating is limited. It will give you a nice overview of the city and allow for you to get some really great pictures! If you were only going to do one-paid tour of the city, this is the only one I would suggest. This is one of my absolute favorites!

Navy Pier & Chicago Riverwalk

Take a taxi/bus to Navy Pier and then following the Riverwalk back into the downtown area. You do not need to buy tickets at Navy Pier and you can simply walk along the boardwalk and explore independently.

The Bean! & Michigan Avenue

For a truly iconic "Chicago" picture, find The Bean (Cloud Gate) along Michigan Avenue. The structure is also close to the Art Institute as well as some other famous Chicago features such as the Buckingham Fountain. From here, explore Michigan Avenue which has various retail shops, restaurants, and cafes for exploring!

Skydeck

https://theskydeck.com/

See Chicago from atop one of the former tallest- buildings in the world! While it has had limited hours due to the COVID pandemic, this used to be a very popular site for tourists to take a picture overlooking the city! You may be required to purchase a ticket, unless you were interested in the Chicago CityPass which offers additional sites included in the package.

Neighborhood Exploring

Chicago is made up of 77 community areas that are often grouped into 0 districts or "sides" of the city. While this may seem daunting, some of the most easy and fun neighborhoods to explore are as follows: Pilsen, Chinatown, Little Italy, West Loop, Milwaukee Avenue, Wicker Park, Greektown, Logan Square, and Lincoln Park.

Must Eats

Chicago Style Hot Dog - The Weiner Circle

2622 N Clark St, Chicago, IL 60614

Get a hotdog "with the works" and the place will speak for itself! (Literally)

Italian Beef Sandwich - Al’s Italian Beef

1079 W Taylor St, Chicago, IL 60607

Get the Italian Beef Sandwich, with Gardinara peppers if you like it a bit spicy. Ask for it "dipped" if you want the full experience!

Deep Dish Pizza - Lou Malnati’s

1120 N State St, Chicago, IL 60610

Personal slice or whole pizza, just try the deep dish. A fork and knife will be required for this slice of heaven and Chicago specialty.

Extend for 2 Days ~ Visit Milwaukee!

A 90 minute drive from Chicago, this city holds a special place in my heart as my hometown. Places to visit along the way include: Mars Cheese Castle & The Brat Stop in Kenosha, Wisconsin.

In Milwaukee, explore the Art Museum, do the Miller/Coors Brewery Tour, and then explore a number of the neighborhoods including: Water Street, Brady Street, or the Third Ward.