10 things you have to do in chicago

We loved our time in Chicago! There is so many things to do in Chicago and we have narrowed them down to our top to. Have a read and enjoy!

Chicago offers a variety of attractions to suit the whole family, as well as being a romantic and relaxing place for couples. Strolling through the neighbourhoods and visiting Chicago’s great bars and restaurants is one of the best ways you can spend your time in Chicago but for those who wish to explore more, this is our top 10 things to do in Chicago. The Chicago Pass can help you save quite a bit of money if you are planning on visiting all the top attractions during your stay.

If you are heading to Chicago for a few days, make sure you read this 2 day Chicago Itinerary. 

Things to know before you go to Chicago

Things you have to do in Chicago

10 things you have to do in chicago



A tranquil and relaxing attraction with various sculptures and architecture dotted across the park. The park is open from 6am to 11pm and is located between Michigan Avenue and Lake Michigan. It is home to many famous landmarks including the Buckingham Fountains and Lincoln Statue.



Perfect for a few evening drinks and dinner, head to Navy Pier for a choice of many restaurants and eateries as well as a great view of the Chicago skyline and a few rides and attractions.

10 things you have to do in chicago
10 things you have to do in chicago



Found in Grant Park, the Cloud Gate is a popular and famous landmark of Chicago, making it have its own spot in our top things to do list. A reflective upside-down bean sculpture that is great for a selfie.

10 things you have to do in chicago



Head to Willis Tower to experience the SkyDeck with a glass balcony ledge that overlooks Chicago whilst the rest of the SkyDeck offers sweeping views of the surrounding states. This is open from 10am to 8pm but check ahead of your visit as it can close during poor weather. Entrance costs $19.50 but is also included in the Chicago CityPass.




Watch the Chicago Cubs play in the oldest standing baseball stadium of America. Tickets can be purchased online but it is advised to do so in advance. Read about our experience on our blog or look for last minute tickets on Ticket Liquidator.



Offering 360 degree views of this fabulous city, the 360 Chicago building offers an observation deck with cafe and bar for $19 for an adult ticket. Again, this is included in the Chicago CityPass if you choose to purchase it.

10 things you have to do in chicago



Home to some of the best fashion stores, head to Magnificent Mile for some shopping as well as to eat in delicious high end restaurants.



Chicago’s deep dish pizza is incredible and a must whilst in Chicago. Read our review of Gino’s East Pizza (also seen on Man Vs Food) for more details and pictures.



Head to Lincoln Park and Zoo to meet some gorgeous animals; perfect for families. Open from 7am to 5pm most days, this is the place to enjoy a free day of fun.

10 things you have to do in chicago



One of the things that makes Chicago beautiful is the lakefront and rivers running through the city. For a perfect afternoon, take a stroll along the lakefront trail, stop near a river, enjoy a picnic and unwind.

Chicago is the perfect place to visit, especially for a stopover or for a few days. We spent just 3 days in Chicago but because of the close proximity of these top attractions, we were able to explore everything we wanted to at a casual pace. If you have a few extra days in the city, make sure to take a few day trips from Chicago to see a different side of Illinois.

What do you love about Chicago? Where else should we head to next time? Leave your suggestions in the comments below!

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10 things you have to do in chicago

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  1. This is somewhere I am really looking forward to going in the States – hopefully to be catching a train to San Francisco or Seattle (love train travel and we want to do more in the USA)
    Pinning for later and sharing 🙂

  2. I have a few friends in Chicago who love it there. Now I can see why! And who doesn’t want a deep dish pizza?!

  3. This is really helpful, thank you. I have been wanting to go to Chicago forever (been once when I was a kid) and I can’t find anyone to go with me; they either have been or have different tastes in everything compared to me. lol But I am going to do it, alone. I’ll be following your handy list.

    • Yes definitely go! Maybe opt for a small deep dish pizza if you’re by yourself!! They are very filling!

  4. I have been to Chicago a couple of time but havent seen all the places you suggested. I will make it a point to check out the rest when i visit next time. I am sure my daughter would love to visit the zoo.

  5. Chicago is one of my favorite cities in the US. These are all good tips for things to do in the city. Getting a deep dish pizza is a must and I love walking along the waterfront. It’s been a while since my last visit to Chicago, I should return soon.

    • Aww yeah that deep dish pizza is definitely worth a trip!!

  6. I’ve seen so many pictures of the Cloud Gate on Instagram but never knew where it was. Now I know it’s in Chicago and perfect for funny shaped selfies! You photographed the Willis Tower beautifully you must be proud of that shot!

  7. Chicago was the first “trip” we took together as a couple. We visited during July 4th celebrations and it was amazing. We took a boat cruise from Navy Pier out onto the Lake and watched the fireworks. The views of the lake at night and of the skyline all lit by fireworks was spectacular. It was a big moment for us as we were starting to fall in love. So yeah, a boat cruise on the lake might be added to the list. 🙂

    • Wow being there for July 4th must have been amazing! aww cute! Our first trip together was to Niagara Falls but our boat cruise (maid of the mist) doesn’t sound quite as romantic as yours!! 🙂

  8. I’ve only been to Chicago on business so I’ve never gotten to experience any of these things. I’ve heard Navy Pier is amazing tough. I also never knew the actual name of the bean-shaped sculpture. I’m embarrassed to say I always thought it was called The Bean. Lol.

    • Navy Pier is great fun and I think that is it’s nickname so don’t feel bad!:)

  9. Well, in Chicago, you can’t leave without trying the deep dish pizza! This one you’ve featured here looks so amazing – and I love that creative tip! It must be really good to have such a long queue!

  10. I really want to visit Chicago, so I loved reading this post. 🙂 So many great suggestions and ideas. Definitely saving this for when I do visit someday!!

  11. I’ve always wanted to visit Chicago purely to see the Cloud Gate! Funny thing is that I’ve always thought it was called the Chicago Bean for some reason!

  12. Your post reminded me of our time in Chicago. We were inChicago for 2 years and my younger one was born there. Navy pier was our favourite. #citytripping.

  13. I’ve pinned this – wanted to go to Chicago for so long! #citytripping

  14. I am definitely making a note of this – Chicago is somewhere I’ve wanted to visit for a while, so love the tips. I wonder how many photos I’ll end up taking of the bean! Thanks for linking up with #citytripping

  15. I have one good reason I should visit Chicago – my cousin lives there! And yet I’ve still never been. It looks incredible.

  16. This is perfect, thank you! Leaving for my first ever trip to Chicago tomorrow- Can’t wait! Everyone I speak to seems to love this city!

    • Have a fantastic time!!

  17. A great list! As a former Chicagoan, I appreciate the love <3 🙂

    Buuuuuut I do have to take issue with a few things, as is tradition:
    – Navy Pier is great for an afternoon but there are so many better restaurants and bars for a dinner or drinks! Just head to River North and you wont be disappointed.
    – it's the Sears Tower, Wrigley Field, and it's still the Hancock!! haha 🙂
    – Thank you thank you thank you for pointing out Grant Park and the Lakefront trail. The trail is probably my favorite thing about the city, along with the stretch of green that follows it. Grant Park, Millennium and Maggie Daley Parks, and Lincoln Park up north. It's truly the city's treasure.

    Thanks for sharing! Now I miss home :/

    • Thank you for your comment, yeah we found the Navy Pier a romantic area as a couple but there are definitely loads of nice restaurants and bars elsewhere too! We loved the parks, they are so beautiful and the Lakefront trail was a favourite of mine!

  18. […] I hope you enjoyed this mini guide to Chicago street art, aka murals in the Pilsen and Wicker Park neighborhoods. All you need to do is put on your walking shoes and explore these neighborhoods with an eagle eye out for murals. 16th and 18th street on Pilsen (starting from the National Museum of Mexican art to Loomis) have several murals along the way. In Wicker park, Damen Avenue, Milwakee avenue and Division street have murals on store sidewalls. Finally, if you do visit Pilsen, do not give the free National Museum of Mexican Art a miss. Their exhibits are some of the best that I have ever seen. Read my other posts on Los Angeles murals here and Austin murals here. Finally, if you are looking for fun things to do in Chicago, read Katie’s guide on top 10 things to do in the Windy City! […]

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