Epic Long Weekend in Chicago: Top 20 Things to Do!

Take it from me guys, Chicago is one epic place to be, especially in the summertime. I mean, who would turn down an easy weekend getaway? Not me, that’s for certain. In any case, read along for planning a long weekend in Chicago and top things to do in Chicago!

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(1/20) Take an Architecture River Cruise

No joke, this legit needs to be the first thing you do on your long weekend in Chicago. I was originally in the camp that it sounded kind of boring, but the guides are awesome and know a ton about the city. I learned more about architecture than I thought I’d ever know. Plus, it’s on a boat, and everyone knows life is better on a boat. Another option is to hop on a Chicago Lake Cruise Tour.

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(2/20) Millennium Park

A first-time visit to Chicago isn’t complete without a visit to Millennium Park. You can find everything from iconic Chicago sights (the Bean) to cutting edge art to outdoor concerts. It’s an awesome spot to bring your picnic blanket on a summer day.

(3/20) Take a Photo with Cloud Gate

Also known as the Bean, taking a selfie with this giant structure is easily one of the top things to do in Chicago. Let’s be real…you haven’t really gone to Chicago unless you’ve posted an Insta of the Bean.

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(4/20)Explore Navy Pier

Navy Pier juts out over Lake Michigan and is the perfect spot to spend an evening. Whether you’re looking for thrill rides, a beer garden, or fireworks, the pier has the makings for a fun evening.  Another cool way to experience the fireworks is with a Segway & Fireworks tour!

(5/20) Ride the Ferris Wheel

While you’re at Navy Pier, give into your inner child and ride the Ferris wheel. You get awesome views of Chicago…bonus points if you can go at sunset!

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(6/20) Check out Chicago’s Comedy Scene

So everyone told me to get tickets to Second City, but I waited until the list minute and obviously there were no tickets left. On the plus side, I went to a hilarious show “Date Me” at UP Comedy Club, and can safely recommend it. I was nearly crying by the end I was laughing so hard. In any case, this definitely NEEDS to be part of your long weekend in Chicago.

(7/20) Watch the Show at Buckingham Fountain

You can find Buckingham Fountain in Grant Park (even though it sounds like it belongs in the U.K.). The fountain puts on a show every hour on the hour 9AM – 10PM. In the evenings, it comes alive with lights and music!

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(8/20) Chow Down at Billy Goat Tavern

Billy Goat Tavern is another Chicago staple…order the cheeseburger. You won’t regret it (except if you’re on a diet or wearing tight jeans, and then you 100% will, sorry.)

(9/20) Experience the Skydeck

Zoom up to the top of Willis Tower and take in the beautiful cityscape. The Skydeck is a glass-paneled box that will give you a view straight down!

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(10/20) Get Your Knowledge on at the Museum of Science and Industry

Ok, so this museum is sadly not located in the Loop, but it’s an easy bus ride away! There’s a general admission fee ($18 for adults and $11 for kids), but if you have a Go Chicago Card or CityPASS, it’s included in your ticket. There’s a little bit of everything at the museum…you can learn about storms, farm technology (actually super cool!), the history of bicycles, and so much more. I’m a not so secret nerd, so I always love learning something new.

(11/20) Root for the Cubs at Wrigley Field

Bonus points if you use Lakefront Trail to bike up to Wrigley Field! I’m honestly not a huge baseball fan, but the Cubs are definitely a fun team to watch.

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(12/20) Befriend the Polar Bears at Lincoln Park Zoo

My favorite thing about the zoo is that it’s free (also the polar bears melt my heart)! If you’re in the area, it’s easy to swing by for a couple hours and befriend the animals.

(13/20) Watch a Sunset from John Hancock’s Signature Room

Pop up to the 95th floor of the John Hancock Center to the Signature Room. You get awesome sunset views to go with your drink. Ladies: you also get insanely gorgeous views from the bathroom. Gents: I’m sorry, you have no views from your restroom. Finally a case where it’s lucky to be a lady!

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(14/20) Grab a Hot Dog at Portillo’s

I’m definitely not typically a hot dog lover (popular nicknames in my family for hot dogs include “tube steaks” and health missiles,”) but you can’t beat a classic Chicago-style dog. While you’re there, might as well splurge for the fries and shake too, am I right?

(15/20) Take a Walking Tour of the City

Check out Chicago’s walking tours—I’d recommend the Gangsters and Ghosts Walking Tour, and get in touch with the city’s colorful history. You’ll get to explore the dark side of the city as you walk through the Loop District.

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(16/20) Order a Deep Dish Pizza at Giordano’s

You’re going to have to trust me when I say that your Chicago experience will not be complete with a deep dish pizza. I’ve had one before, but it was definitely not quite like this. There was so much sauce and cheese, I thought I had died and gone to heaven. A long weekend in Chicago isn’t complete without a deep dish pizza!

(17/20) Bike along Lakefront Trail

Lakefront Trail stretches 18 miles up Lake Michigan and is one my favorite spots in Chicago. Grab a bike and explore the lakefront while getting your exercise in. If you believe in balancing out exercise with delicious food (yes please!) check out this Bikes, Bites, & Brews Tour.

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(18/20) Shop the Magnificent Mile

If you have some extra cash, the Mag Mile is the place to shop. If you’re like me, window shopping is equally fun, and a lot easier on the wallet. If nothing else, the Magnificent Mile has incredible architecture, and is always touted as one of the top things to do in Chicago and a definite to-do on your long weekend in Chicago.

(19/20) Visit the Chicago Theater

Even if you can’t score tickets to the theater, swing by and capture a pic with the iconic sign. There are also theater tours if you’re absolutely dying to get in!

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(20/20) Enjoy the Hop-On, Hop-Off Bus

There’s no easier way to see the top things to do in Chicago than taking the hop-on, hop-off bus. Jump up at iconic Chicago landmarks to make the most of the city in little time! This is an easy way to make the most of your long weekend in Chicago.

Other things to do on a long weekend in Chicago:

Sadly, for long weekend trips, I can’t partake in everything the city has to offer, but there are a number of other things to do on a long weekend in Chicago that I’d love to check out. If you have even less time than a 3 day weekend, click here for ideas on how to spend 2 days in Chicago. Here a few of my top options:

  • Chicago Crimes Night Tour – Learn about Chicago’s most infamous mobsters and gangsters.
  • Blue Man Group – Experience the magic and entertainment that is the Blue Man Group…there’s nothing quite like it.
  • Chicago Underground Donut Tour – Eat your way through dessert boutiques in the Windy City…I never say no to snacking on sweets!

Where to Stay in Chicago

Hotel Deals: My top choice is probably  Expedia—I’ve found some insanely cheap (beautiful) hotels. Personally, I stayed on the Mag Mile, and absolutely loved the location…it can be a little pricey, but the location is awesome!

Read More:

Basically, I’m a pro at long weekend trips since I always have to work around that vacation time. For more long weekend inspo, check out these ideas:

So, I hope you found this guide on top things to do in Chicago helpful. If you haven’t been, it should definitely be on your bucket list!  Tell me—have you visited Chicago and loved it as much as me? Let me know some of your favorite things to do on a long weekend in Chicago in the comments!

Pin for Later!


  1. Having been to the Windy City many times to visit family, Chicago also has good BBQ and Blues/Jazz. There are a plethora of jazz clubs to look up. A Blues club I really likes is Kingston Mines. Easliy gotten to on the El train. They have BBQ and other food and long picnic style tables and 2 stages. http://kingstonmines.com/

  2. I’ve pinned this for when I get to Chicago. Some really fun things to do. The architecture river cruise and the city walking tour are right up my alley and I’d have to check out the view from the loo on the 95th floor! 🙂

  3. I lived in Chicago for about two years and there are some things from your list that I haven’t done and will probably do next time I’m there this October. Lovely post! I miss Chicago #mysecondhome

  4. I’m headed to Chicago next month so this post was RIGHT. ON. TIME. Can’t wait to see those views for myself!

  5. We’re visiting next spring so I am totally book marking this. Plus that architecture tour sounds right up my street. And, how early did you need to get up for that picture of the bean!??? Every other photo I’ve ever seen has always had way too many people in it – you must have camped out the night before 😉

  6. I lived in Chicago for six years, and this makes me want to go back and do everything again. I’ve done the architecture tour three times, and I always recommend it to people visiting. I’ve never gone inside the Chicago Theater, but it’s on my list for the next time I go back.

    1. One of my friends there had recommended the architecture tour, and I was so skeptical (it sounds boring), but ended up absolutely loving it! So cool to get a preview of the city and learn about the history and architecture at the same time.

  7. Heading there for the first time next month. Your list gave me a lot of great ideas for places to visit and things to do — thank you!

  8. Chicago is one of my favourite places in the world – I support all the sport teams from there so going to Wrigley Fields to cheer on the Cubs was one of my most special experiences ever! I am actually thinking of heading back in a few weeks to watch hockey, baseball and explore the city even more so I might be in touch about more tips! Definitely saving this for later!

    1. Oh I bet the Cubs game was even more awesome for you! I loved the atmosphere there, but am definitely not a Cubs fan so it’s not quite the same. Feel free to reach out if you need any Chicago tips 🙂

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