10 Ways to Experience Chicago

To my shame I went into Chicago with low expectations, and I’m incredibly happy to report it went above and beyond anything I could’ve expected. My main worry being that there wouldn’t be enough to do, but boy was I wrong. As this post will detail, there is plenty to do in the Windy city.

If you’re planning a trip to Chicago anytime soon, or hadn’t thought of it at all before, please take a look at the below! There’s so much to do on the trip, and we still left wanting to spend more time there – which is a great sign of a good holiday if you ask me.

Millennium park

One of the most iconic images of Chicago has to be of ‘The Bean’. It really was great to see it in person, nothing a picture can quite convey!

The best way to explore Millennium Park is just to walk around and enjoy, preferably with a coffee in hand! In the Spring there are free open air concerts at the park too, so if you’re visiting then it’s a great opportunity to enjoy an evening for free.

Try the Deep Dish Pizza

I mean, can you go to Chicago and not try a deep dish pizza? It’s a serious treat, and I love how the waiters we encountered were very honest with the portion sizes, advising us to stick with small – rather than overselling to us. We could only manage a small pizza to share between two, because they’re just so deep and delicious they’re incredibly filling.

Whilst there we ate at both Pizzaria Uno and Labriola to try their signature pizza pies, and we were not disappointed. And a heads up if you go to Uno, the ‘cheese sticks’ are more than just an appetiser…

Lake front trail

Walk, run, cycle or even roller blade it, there are plenty of ways to enjoy the city’s Lake Front Trail. It’s a 18 mile stretch of pavement that spans along the side of the city and Lincoln Park, which provides incredible views of the city and the Lake.

We started at the park and made our way down, past the Navy Pier and finishing at the Planetarium. It’s a great way to spend an afternoon if you’re lucky enough to have good weather!

The Signature Room

I feel like this should be my catchphrase at this point, but I’m a big believer in finding a rooftop bar that’ll get you a better view than a pay-for viewing platform. Luckily Chicago has just that!

On the 95th floor of the John Hancock Skyscraper you can stop for a drink or a bite to eat at the Signature Lounge. Granted, you may have to queue and make sure to specify if you’re willing to wait for a window-side table. We did – and we only waited for approx 10 mins – and our view was incredible!

On the day we went there was an apocalyptic-looking haze over the city, but it just made the view more spectacular. As with all rooftop bars I’d definitely recommend trying to visit in both the day – when it should be quieter – and at night, because the different views you can get for the different time of day are so worth it.

Wicker park
If you’re in the mood for some vintage shopping or brunch then head over to the Wicker Park earlier. Granted when I was there I wasn’t in the mood to shop, but the vast amounts of vintage and concept stores on offer were a lot. I can’t vouch for them myself but the vintage stores I was recommend were Moon Voyage and P.45.
If you’re not up for a shop like I was then there are plenty of spots for a drink or something to eat, even just so you can sit back and people watch, which is always a great – and cheap – way to experience a new city.


Architecture tour/river walk

Chicago is the home of the skyscraper after all, and what better way to take a look than from the river?

The architecture tour was recommended to us a lot in the lead up to our trip and I can definitely join in the party and say it’s worth it. We chose the Shoreline Sightseeing Tour mainly because it was the cheapest on offer, but also the highest rated on TripAdvisor.

If an hour architecture lesson really isn’t your bag then you can still enjoy the river along the River Walk which is dotted with bars, cafes and spots to sit and enjoy the view.


My time at The iO Theater in Chicago was shamefully my first time at Improv comedy and I can now say I’m a huge fan.

We saw ‘Whirled News Tonight’ which lasted almost 2 hours – a pretty good bargain at $16 a ticket! As with most shows in Chicago they offer table service for food and drink so we never went without.

If you’re in Chicago for the evening then definitely make Improv high on your list to enjoy. Both the iO theatre and Second City offer shows throughout the week and provide a great night of entertainment.

Live jazz

Chicago is known for it’s tradition of live music, and there are countless jazz and blues spots around the city to enjoy. When we were in town we actually saw some live Blues at Blue Chicago and it was an absolute treat.

There’s really nothing as enjoyable as live music, and in such a small and intimate setting it was a great way to enjoy the evening with a few drinks.

Visit the Chicago Cubs at Wrigley Stadium

Granted, we didn’t get the chance to do this during our visit as the season hadn’t started yet. However in absence of any baseball to watch (apart from on TV, because trust me, it’s always on TV) visit the Sluggers bar opposite the stadium and have a go yourself!

The sports bar has daily discount deals, a proper, bargain sports bar style menu and the added bonus – batting cages upstairs. We visited on a rainy day and we had such a good time. For $2 for 10 tokens – which provide 10 batting goes each – we started off in the ‘slow’ cage before my graduating to the ‘medium’ – but even a slow ball was hard to hit for me!

I would definitely recommend Sluggers for a an afternoon playing baseball, but if you’re visiting in Summer and the option to see the Cubs play is there I would also definitely give that a go! The atmosphere would be incredible.

Navy Pier

Yes, it may be a tourist spot but if you’re a tourist then why not! It doesn’t take too long to do a lap of the pier, but if you’ve got good weather like we had then there’s no harm in sitting in the sun to watch the tourists walk past and look out at Lake Michigan.

We chose to stop by Jimmy Buffet’s Margaritaville – seriously don’t judge me – as they offered strong, cheap and large margaritas to take away which meant we could sample several out in the good weather.

And there we have it! A round up of what to do in Chicago as what I’ve only experience – because there’s plenty more to enjoy.

I hope you enjoyed this post, more Chicago posts will be coming to the blog every week, but in the meantime my holiday snaps can be found on my Instagram @GrundyTravels.

Thanks for reading x

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