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12 essential activities for a weekend in Chicago

12 essential activities for a weekend in Chicago

Chicago has been on our to-do list ever since we moved to USA.

Last weekend, we finally made the trip from NYC to the midwest! I absolutely love that satisfying feeling of ticking off a destination that’s been on our list for a while.

I’d briefly visited Chicago 5 years ago but I’d only just scratched the surface, and Rob had never been. 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 my recommendations for a weekend in Chicago.

HI Chicago Hostel

Where we stayed:

Rob and I based our trip at the HI Chicago Hostel. The rooms were clean and spacious, and the bed was super comfortable – I don’t think I’ve ever slept so well in a hostel as I did here.

The lounge and breakfast area were warm and welcoming, with plenty of sunlight pouring in through the floor-to-ceiling windows. My creative side also got a tad excited when I noticed the fun neon sign in the lounge area, and the street art wall in the lobby.

The hostel is located downtown, right on ‘the loop’, which made it incredibly easy to catch a train to anywhere in the city. There was also a kickass sandwich place next door (Cafecito) and a hipster coffee shop around the corner (Hero Coffee Bar).

Architecture Boat Tour Chicago

1. do an Architecture boat tour

This activity was recommended by everyone we talked to, even the Chicago locals. I usually steer away from paid sightseeing activities, but I’m glad we splashed out on this.

The Chicago Architecture Boat Tour is offered by a few companies. We went with Wendella Boats, which cost $35 per person. The tour lasted 75 minutes and took us up three branches of the river.

I never really thought that skyrises would be very interesting, but this tour totally proved me wrong – the narration showed us 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 in my opinion 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.

Deep dish pizza Chicago


After spending the past year consuming oversize slices of thin-crust NYC pizza, I was fairly curious to see how a Chicago deep dish pizza would compare.

We went to Lou Malnati’s for our deep dish pizza. The wait for a table on a weekend night was rather lengthy, so we ended up getting our pizza to go and eating it in the park.

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. Still, it was actually really tasty and I thoroughly enjoyed it. Thumbs up for deep-dish pizza.

Chicago Theatre

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


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 (our one and only weakness).

If you’re travelling 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.

#funfact: The original ferris wheel was actually invented right here in Chicago by George Washington Ferris, who designed it for the World’s Fair in 1893.

The Signature Room, Chicago

6. Get up high for some views

As has become a habit of mine, I looked for a high-level bar or café to see some views instead of paying for an observation deck. I managed to find one in John Hancock Tower!

The Signature Room is on the 96th floor, which is actually two floors above the observation deck. A drink here will set you back between $10-$15, which is cheaper than the $20 you’d pay for 360 Chicago and you get a glass of beer or wine while you enjoy the view.

We actually attempted to go to The Signature Room twice. The first time was on a Saturday night for sunset, which was a huge mistake as the line to get up was 1.5 hours long. We immediately gave up and instead came back on Tuesday at 11:30 AM. This time, we got in right away and were two of only a handful of people up there.

Aside from John Hancock Tower, 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. It sounds like fun, though this option is more pricey than the others.

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 Conservatory, 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!

9. sip on some fancy cocktails

Chicagoans seem to love their fancy cocktails. One of my favourite 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.

Greetings from Chicago mural

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 colourful 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 favourite 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.

Wrigley Field

Image from Wikipedia


Unfortunately we didn’t get the chance to see a Cubs baseball game, but it was recommended by a few people as a great activity for a trip to Chicago. Apparently 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.

12. Hit up some museums

Chicago has loads of museums that would be perfect for a rainy day. Again, this is something we didn’t get a chance to do, but here’s some to choose from if you have the time:

*I was a guest of HI Chicago Hostel during my stay. I’m proud to be an honest and transparent blogger, so every opinion expressed on AGWT is a true review of my experience!

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15 Responses to “12 essential activities for a weekend in Chicago”

  1. Caitlin

    Fantastic post – I used to live in Chicago and you absolutely hit the nail on the head with the key things to do! If you like fancy cocktails, be sure to check out Pops for Champagne and Watershed (they’re in the same building so you can hit them both up in the same night) next time you visit!

    • Ashlea Wheeler

      Ooh thanks for the recommendations, Caitlin! It’s good to know that I did a good job of covering Chicago in one weekend 😀

  2. Ray

    I was in Chicago about six weeks ago, but the Cubs were on the road. As an alternative, I did the Wrigley Field Tour: That is highly recommended if you do not get to see the Cubs play at home.

  3. Monika

    Thanks so much – all of these tips look awesome! I just moved to Chicago today so will certainly be ticking them off one by one! (Especially the Cubs game!)

    • Ashlea Wheeler

      Oh wow, that’s so exciting that you’ve moved to Chicago! I have some friends who used to live there and they loved it 🙂 Good luck with all the activities, Monika!

  4. Nitanja

    Love this article! Where did you take the welcome picture ? The first picture.

  5. Sveva

    Just want to let you know that I myself am a travel blogger as well and have been looking for things to do in Chicago. Your travel guide was one of the most original I have found thus far! Thanks for sharing all of the cool spots like the murals in Logan Square and the iconic Chicago theatre. Keep up the good work! 🙂

    • Ashlea Wheeler

      I’m so glad you enjoyed my list, Sveva! I’m sure you will have an amazing time in Chicago 🙂

  6. Candace Young

    Well written! Unfortunately, I stumbled upon this post after our trip to Chicago but you hit the head on many things we did while in Chicago! I will have to go back, just to visit the Signature Room you are talking about, the view looks amazing! Great read!

    • Ashlea Wheeler

      Thanks Candace! I’m so glad you enjoyed your trip to Chicago. It’s such a great city! Definitely worth a second trip, I think 😀


      The Signature Room is a MUST! If you want to see one of the best views in Chicago- go to the ladies room in the Signature Room!!!!!!


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