We loved our time in Chicago! There are so many things to do in Chicago and we have narrowed them down to our top 10. 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 neighborhoods 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 you have to do in Chicago

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

NAVY PIER
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.

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

WRIGLEY FIELD
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.
360 CHICAGO – FORMERLY KNOWN AS THE JOHN HANCOCK CENTER
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.
MAGNIFICENT MILE
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.
DEEP DISH PIZZA
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.
LINCOLN PARK AND ZOO
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.

CHICAGO LAKEFRONT TRAIL
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.
THE FIELD MUSEUM
The Field Museum is a huge natural hits museum and one of the best museums in Chicago for kids. It is home to a permanent collection of fossils and dinosaur remains, with Sue a Tyrannosaurus rex, being the most popular sight here; Sue is physically the largest Tyrannosaurs rex specimen ever discovered.
The Art Institute of Chicago
Located in downtown Chicago, the art institute of Chicago is arguably one of the best art museums in the USA. You can find famous pieces of artwork from Edward Hopper and Grand Wood but also appreciate the incredible architecture of the museum too. The art museum is also included in the Chicago City Pass.
What do you love about Chicago? Where else should we head to next time? Leave your suggestions in the comments below!
Helpful Resources
Travel essentials:
- We LOVE this camera for our travel photography.
- For a cheap, easy, and compact camera, we use this to vlog and take photographs.
- We use this microphone for all our Youtube voiceovers.
- We use this travel drone (but make sure to check drone laws in your chosen destination first).
- This is our favorite travel insurance because it covers so many activities and travel situations that could arise on longer trips but also offer year coverage.
What to pack
- No matter where we travel, I always take these trusty hand sanitizers and a mini first aid kit.
- We love these toiletry bags (especially great for smaller bathrooms) and choose a laptop bag like this as our hand luggage.
- We keep our devices charged on long travel days with these lightweight battery packs and bring these worldwide travel adaptors on all our trips.
- I still struggle not to overpack so stick to using an expandable suitcase like these and always take my trusty luggage scales to avoid being charged at the airport.
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