Weekend in Chicago

Chicago is one of our favorite cities to explore. There is always so much to see and do. But if it is your first time, or if you don’t have too much time to see the city, we’ve broken down popular attractions that will help you hit the most important parts.  

What to do for a Weekend in Chicago


The Famous Chicago Skyline 

The Shedd Aquarium, the Adler Planetarium, and the Field Museum are all in the same area on a plateau of Lake Michigan. If you have time, we recommend checking out each of these places, but if not, at least drive to them to see the most beautiful view of the skyline. It is beautiful both day and night, so if you have time, try to go see it in the daylight, and when the buildings are all lit up. 

For the football fans, Solider Field is also very close as well.

Chicago Skyline

The Chicago Bean

The famous mirrored bean shaped sculpture in Chicago is called Cloud Gate. It is in the center of Millennium Park and is a fun place to stop for some great photos. 

Chicago Bean- things to do in Chicago

Buckingham Fountain 

Just a short walk to Grant Park, you’ll be able to see Buckingham Fountain. This fountain is typically only going during the late Spring, Summer and early Fall seasons depending on the weather. It’s definitely worth a quick stop if you are visiting in the warmer months. 

Chicago River Cruise

Chicago is such a unique city because it has the river running right through the center of all the large skyscrapers. The best way to see each of these is to take a, Architectural River Cruise. We recommend riding with Chicago’s First Lady Cruises. Their boats have an indoor and outdoor space, so if it is cold and rainy, like it was when we went, we were still able to stay warm and cozy while still being able to see all the buildings around, thanks to their large windows. They also provide bar and beverage and snack services, so you can enjoy your 90 minute cruise.  The Architectural Cruise was very informative, and we enjoyed learning about the history of the city. We loved our time aboard Chicago’s First Lady, and recommend them to everyone who is looking to cruise on the river. 

Chicago's First Lady Cruise
Chicago's Classic Lady Cruise _ River Cruise in Chicago

Chicago Riverwalk

Chicago Riverwalk will always have a special place in our hearts, as that is where we got engaged.  Take a walk in the city, along the river for a nice relaxing stroll. In the warmer months, you can rent a bike and ride down the walk, or rent a kayak and paddle through the river. Definitely one of our favorite places in the city. 

Chicago Riverwalk - Things to do in Chicago

Navy Pier

Of course no trip to Chicago is complete without a visit to Navy Pier. Head out to enjoy Lake Michigan, ride on the ferris wheel at the end, or check out the shops and botanical gardens inside the buildings. 

Chicago's Navy Pier - Things to do in Chicago

Willis Tower (a.k.a. Sears Tower)

It will always be Sears Tower to us, but now named Willis Tower. This building was once the tallest building in the world for 25 years until the 1990’s. It now stands in the 21st spot, but is still an impressive place to see. Head up to the 103 floor and enjoy the beautiful views of Chicago’s city. 

Cubs Game

As baseball fans, we can’t leave off enjoying a game in Wrigley Field. We were lucky enough to see a World Series Playoff game vs. the Dodgers (our Los Angeles team), and enjoyed the beautiful night. We recommend trying to catch a game while you’re in the city. 

Chicago Cubs Stadium - Wrigley Field

Chicago Fire

If you happen to be a fan of the NBC television shows, Chicago Fire, Chicago Med, or Chicago P.D., you’ll have to check out Lotties bar, knowns as “Molly’s” in the TV Series. It is “Molly’s By Day, Lottie’s By Night”. It’s a fun TV set open to the public for Chicago Fire fans. 

Chicago Fire TV Show Bar

If you just have a couple days in Chicago, theres tons to see and do that will keep you pretty busy. These are some of our favorites, and they can definitely all be done within 2 days, as we did this exact itinerary.