What to Do During a Weekend in Chicago


In 2018, Chicago set a record of tourists, with 58 million people visiting this incredible city. While the pandemic put a dampener on city breaks, it’s only set to rise from now on as people discover just how amazing this place is.

If you have a weekend in Chicago, you might be wondering what you should squeeze in during your limited time.

There are the things you absolutely must do.

River Cruise

The Chicago River runs through the center of the city, providing great views from its surface. There are many different boat trips you can take through the city, from a romantic dinner cruise to a fun cruise with cocktails you can take with friends.

There’s a boat trip to suit everyone, so do your research and find the one for you.

This is an ideal way to see the city!

Sample the Food

When taking a trip to Chicago, it’s essential to sample the food.

Chicago is known for a few things! There’s the hotdogs, which come loaded with a variety of different, unusual toppings and can be found around every corner as quick street food to eat on the go. Check out Portillo’s if you want to be a real local.

Then there’s the pizza. Chicago is known for its deep-dish pizza, which many people argue is more of a pie than a casserole. If you love cheese, pick one of these up — you’ll likely only be able to manage a couple of slices since it’s so thick!

There’s also some gourmet popcorn to be found if you’d prefer something on the sweeter or lighter side of things.

Check Out the Bars

Chicago has a number of really unique bars. If you like a cocktail or two, or just want to be out at night, make sure you stop by a few of them.

Into tiki drinks? Check out the famous Three Dots and a Dash. There are two rooms here depending on whether you want a more intimate experience, though you’ll likely have to make a reservation since this place fills up fast.

There are also some great arcade bars, such as Logan’s Arcade, for those who love something to do while they drink — like gaming.

If you’re more of a beer person, there are some amazing breweries and bars with some great craft beer.

The Chicago Observation Deck

1000 feet above Chicago is 360Chicago, an observation deck that lets you see over the city. For those who are afraid of heights, you might want to avoid this one — but if you love the thrill and breathtaking views, then head up to the observation deck.

There’s also TILT, a moving platform that tilts 30 degrees down towards Chicago at 1,030 feet. This has been known to make many feel ill but is truly a once-in-a-lifetime opportunity and will make you glad you did it when you walk away.

There’s also a bar at the top so if you need to soothe the nerves of being up that high, you can indulge!

Go to the Museums

Spend your days wandering around the museums, one of the best things to do in Chicago due to the history you can find there. The Museum of Science and Industry is high on the list, as well as the Field Museum and Chicago History Museum.

Whether it’s science you want to explore or the history of the city, Chicago has you covered. Some museums are even free to enter so you can browse what they have to offer on a budget.

Check Out the Art

As well as museums, you can’t possibly consider going to Chicago without checking out the art!

The Museum of Contemporary Art is a great place to go and experience the visual beauties Chicago has to offer. There’s also the Hyde Park Art Center and Chicago Arts District for those who are super into art.

You may not have time to check out all of these things, so do your research on which best suits your tastes. You’re not likely to be disappointed by any of them.

Visit Millennium Park

Millennium Park is, perhaps, one of Chicago’s most famous attractions — so if you’re considering a weekend Chicago Vacation and have never checked it out, now is the time.

It’s a beautiful park in the middle of the city and right at the heart of it is Cloud Gate — a sculpture more commonly known as the Bean.

The Bean is made up of 168 stainless steel plates welded together and creating a reflective surface, so you can take that iconic selfie. The Bean is usually pretty busy with tourists on weekends so if you want a better picture, head there on a weekday if you happen to be around on Friday or stick around for Monday.

There’s also the Crown Fountain, the Lurie Garden, and various other great attractions around the park. It’s perfect for a stroll on a nice day.

Do These Things During a Weekend in Chicago

If you have a weekend in Chicago, it may seem hard to cram everything in — and that’s because it is! There’s so much to do in Chicago, and you can’t possibly fit it all in during one weekend.

However, that just means you have a plethora of activities and sights to pick from. Pick what aligns with your tastes best… and if you can’t fit everything in, then that means you’ll have to come back.

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