We turned to some of our friends who had lived in Chicago, and asked them to tell us which essential activities we should do while we visited. Their local suggestions mixed in with a little sightseeing gave us an awesome Chicago experience! If you’re also planning a trip to the city, here are 12 things to do in Chicago.


Chicago Illinois1. DO AN ARCHITECTURE BOAT TOUR

This activity is recommended by everyone, even the Chicago locals. A Chicago Architecture Tour lasts about 75 minutes and took you up three branches of the river. The narration shows you that the Chicago downtown area is more than just a cluster of tall buildings – each one has a unique story.

Cloud Gate, Chicago

2. TAKE A WALK THROUGH MILLENNIUM PARK AND GRANT PARK

These parks are situated side-by-side in the downtown area. They can get pretty crowded with tourists, but it’s easy to see why. Grant Park is large and pleasant to wander through. Here you’ll find Buckingham Fountain, rose gardens, a rock climbing wall, and some sports fields.

If you take the artistic pedestrian bridge across to Millennium Park, you’ll find the famous Cloud Gate, which looks like a gigantic reflective kidney bean. Head here early in the morning if you want to see it without the hoards of people crowding around.

Where to stay: Swissotel Chicago

Deep dish pizza, Chicago

3. EAT SOME DEEP DISH PIZZA

We went to Lou Malnati’s for some Chicago deep dish pizza. The crust was thick and doughy, and the fillings were almost entirely cheese. It’s so heavy that one or two slices is enough to have you unbuttoning your jeans and moaning about how much you ate. The pizza was actually really tasty – I thoroughly enjoyed it.

Chicago Theatre, Chicago

4. SEE THE ICONIC CHICAGO THEATRE

My mission was purely to take a look at the exterior of this gorgeous theatre. This Chicago landmark has been around since 1921 and has been an unofficial emblem for the city ever since. If you want to do more than just take a photo, you can also get tickets to see one of the events (mostly comedians or musicians), or do a tour of the venue.

Navy Pier, Chicago

5. WALK ALONG NAVY PIER

Navy Pier is probably the most touristy thing to do in Chicago. Personally, I found it rather boring until we arrived at the very end of the pier, where we found pretty views of Lake Michigan and also stumbled across a beer garden.

If you’re traveling with kids and don’t mind lining up for some rides, then there are a few activities half way along the pier that might interest you. The ferris wheel is the most famous – the current wheel is brand new and is one of the most modern ferris wheel designs in the world.

Where to stay: Fairfield Inn & Suites Chicago Downtown

John Hancock Tower, Chicago

6. GET UP HIGH FOR SOME VIEWS

I always look for ways to get up high and see some views! We ended up going up John Hancock Tower, which is where you’ll find 360 Chicago observation deck.

You also have the option of going up to the 103rd floor of Willis Tower for Skydeck Chicago. This is where you can step out on The Ledge – a glass box that extends out the side of the building.

Both 360 Chicago and Skydeck are included in the Chicago CityPass.

North Ave Beach, Chicago

7. HIT UP THE BEACH

As someone who grew up in a country where all the beaches line the ocean, I didn’t expect the freshwater beaches on Lake Michigan to be so good! We hit up North Ave Beach on a hot summer public holiday, and it was busy but not unbearable.

Other less busy beaches can be found further north along the lakefront. The further you get from the city, the quieter they’ll be.

Lincoln Park, Chicago

8. EXPLORE LINCOLN PARK

Lincoln Park sits along the lakefront north of the city. Here is where you’ll find the Lincoln Park Zoo, one of the only free zoos in the US, and also one of the oldest as it was founded way back in 1868.

If you’re like me and not really into seeing caged animals, then head straight to the Lincoln Park Conservatory. There are plants from all over the world housed here – I even found a few from my home country of Australia. This spot is also very Instagrammable, so be sure to take your camera!

Where to stay: PUBLIC Chicago

9. SIP ON SOME FANCY COCKTAILS

Chicagoans seem to love their fancy cocktails. One of my favorite cocktail spots was Sparrow, a 1920s speakeasy theme in the Gold Coast area. Others that were recommended to me were The Whistler in Logan Square, The Aviary in West Loop, and The Violet Hour in Wicker Park.

Chicago Illinois

10. CHECK OUT THE STREET ART IN LOGAN SQUARE

I’m a fan of any area covered in street art, and Logan Square did not disappoint. This colorful suburb is where you’ll find the Greetings from Chicago mural, plus loads more amazing art scattered around the streets. Walk along N Milwaukee Ave around California Station to see the best of it.

While you’re in Logan Square, check out The Chicago Diner. This was hands down our favorite food spot from the entire weekend. It serves local craft beers, fantastic vegetarian pub-style food, and plays VHSs from the 90s on the TV above the bar.

11. SEE A CUBS GAME

See a Cubs baseball game was recommended by a few people as a great activity for a trip to Chicago. Wrigley Field is really nice – it was built in 1914 and is known for having an ivy-covered brick wall, an iconic red marquee over the main entrance, and a hand-turned scoreboard.

Where to stay: Best Western Plus Hawthorne Terrace

12. HIT UP SOME MUSEUMS

Chicago has loads of museums that would be perfect for a rainy day. Here’s some to choose from if you have the time:

  • Chicago History Museum
  • Peggy Notebaert Nature Museum
  • The Art Institute of Chicago
  • The Field Museum of Natural History
  • Adler Planetarium
  • Museum of Science and Industry

Many of these museums are included in the Chicago CityPass, so if you’re planning on visiting more than one of Chicago’s attractions, then check it out – you might just save a few dollars!

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