Top 6 Things To Do in Chicago

by | Nov 2, 2019 | Cities, United States

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One of John’s best friends lives in Chicago, so when we visited, we were able to get some insider tips on what to see and do from a local. I really like mixing in typical tourist activities with local only knowledge, especially when visiting a big city for the first time. I think it’s the best way to really get a feel for the city you’re exploring. Below you’ll find our list of the top 6 things to do in Chicago and an obvious extra that we unfortunately missed out on. You can also check out our video!


1. Bicycle Around Lake Michigan

This was probably my favorite activity of the whole trip. Start your day on the Lake Michigan coast at Montrose beach. This sandy beach is popular among the locals and offers a fair amount of parking as it is a decent way from the hustle and bustle of downtown Chicago. Make sure to remember your swim suit so you can enjoy that refreshing salt-free water.

From Montrose Beach, rent a Divvy Bike. You can buy a pass on your phone from any bicycle kiosk. Then, you just unlock your bike and enjoy. Passes are $3 for a single ride or $15 for the day and there are several kiosks along the bike route, so it’s easy to go exploring and pick right back up where you left off.

Top 6 Things To Do in Chicago: Bicycling

There was also a great bike path that went from the beach into downtown, so we didn’t have to worry about vehicle traffic at all. The path ran parallel to the shores of Lake Michigan almost the entire way until you got into downtown Chicago. The views of the lake and the Chicago skyline were amazing and it was fun checking out all of the beach areas along the way.

Pit Stop: Lincoln Park Zoo

You can ride your bike from Montrose beach all the way into downtown Chicago. We decided to make a pit stop at the Lincoln Park Zoo. It doesn’t have an entrance fee, so it’s a good activity if you are on a tight budget. After refilling our water bottles and checking out the gorillas, we were back on our way.

2. Take an Architecture Boat Tour

This is definitely a touristy activity, but it’s absolutely worth doing, especially if it’s your first time to the city. If you want to make the most of your day exploring, you can do the bike tour in the morning and the boat tour in the afternoon like we did.

Pro tip: there is almost always a Groupon available for these tours, so make sure to check that out before you buy tickets.

We went with Chicago Lakefront Cruises but there are several companies who offer the architectural tours. Our boat had plenty of upper level open air seating providing great views. There was also a big open area downstairs where alcohol and refreshments could be purchased. Parents with restless children who needed to let a little extra energy out tended to gather in the below deck area as it was a safer place for them to move about freely, so you may want to keep this in mind when planning your cruise. If you are looking for something more formal, Odyssey Cruises offers elegant brunch and dinner tours geared towards adults, at a higher price point, however, children are still allowed on these tours as well. 

Top 6 Things To Do in Chicago: Skyline

The tour lasts 90 minutes and takes you down the Chicago River, where you get the best views of all of the skyscrapers. It’s a fun way to learn more about the history of the city. It’s also a good time to play, “How many people on land can I get to wave at me?” John was great at this game with his big wave and goofy grin. The best part was when the tour guide on our boat said, “Wow everyone is waving today, I must be doing a great job.” Nope, you just had John on the boat.

3. Visit the Hancock Building

The John Hancock Building is home to the 360 Chicago Observation Deck and Tilt which apparently “tilts” you outward for views of the Magnificent Mile (umm, no thanks!), but it costs a decent amount of money for these activities. A better option is taking the elevator to the Signature Lounge on the 96th floor.

The Signature Lounge offers sweeping views of the city and the staff do their best to provide you with a window seat if they’re available. It doesn’t cost anything to ride the elevator to the bar and if you want to sit and take in the views, you could always order a soda, or split a cocktail if you’re looking to save money.

Top 6 Things To Do in Chicago: Views  from Hancock Building

I had a very expensive but delicious cocktail and John ordered a less expensive but still pricey beer, and you know what, it still cost less money than going to the observatory two floors below. We didn’t feel rushed or any pressure to buy additional drinks while we were there either. I think the staff knows most people are really coming up for the great views of the city, not to spend the day drinking overpriced cocktails.

Pro tip: The best views of the city are from the women’s restroom-sorry guys! Apparently the men’s room doesn’t even have a window.

4. Try ALL the Food

Chicago has a pretty great food scene and John and I were definitely gluttons while we were there. The city is known for three foods: 1. deep dish pizza, 2. Chicago dogs, and 3. Italian beef sandwiches, but it has so much more delicious food to offer on top of that!

Chicago Deep Dish Pizza

If it’s your first time in Chicago, you have to try a deep dish pizza and Lou Malnati’s is the place to go. Lou started making deep dish pizzas in the 1940s and opened his own restaurant in the 70s. Since then they opened up 56 pizzerias in the Chicago area.

We tried the Malnati Chicago—a classic deep dish pizza. I’d never had a Chicago deep dish before and am used to pizza slices you pick up and eat, so this pizza took some getting used to. It was more like a casserole or pot pie than a pizza and once I wrapped my head around that, it was pretty good (just not like the pizza I’m used to). With that being said, I’m glad I tried it, but I don’t know if I need it in my life as a permanent fixture.

Chicago Dog

If you’re wanting to try an authentic style Chicago dog, look no further than Portillo’s. This Chicago eatery has opened several chains across the country, but they still know how to serve a traditional Chicago dog the right way.

This was probably my favorite “Chicago” food that I tried. Why have I never put hot peppers and a pickle on my hot dog before? I was skeptical at first, with all of the ingredients, especially the tomato, but you know what…it really works! What was John’s favorite part of the Chicago dog, you ask? It was the poppy seeds on the bun. Not even the bun itself. Go figure. Who is this man I married? What a weirdo.

Italian Beef Sandwich

Apparently Al’s is the place to go for Italian beef. I’m not going to lie though, I didn’t love the Italian beef sandwich. Maybe it’s like coconut, you either love it or you hate it? My biggest issue was with the spice mix they used on their meat. Maybe a sandwich from another shop would please my palate a little more? I don’t really know, but I’d give it another go. John did love the sandwich and his Pro tip: Order the sandwich wet so you get extra “gravy” because everything tastes better when it’s messy, right?

5. Take a Stroll On the 606

The 606 is a public park space that runs along the elevated, out of service Bloomingdale Line in Chicago. It’s named for the zip code prefix shared by Chicagoans. The trail is 2.7 miles long and provides a bird’s eye view to the neighborhoods below. It’s a great place to walk, jog, bicycle, or roller skate.

Pit Stop: Ava’s Italian Ice

The trail has 10 access points and the neighborhoods along the access areas are great to explore. I’d highly recommend a stop at Ava’s Italian Ice in Bucktown. It can be reached by taking the Western Access Ramp.

All of the fruit ices at Ava’s are made fresh daily. This was the perfect treat the day we decided to walk the 606 because it was really hot. It also may have been the best Italian ice I’ve ever had. I was worried it might be too sweet, but it was just right. I got a mixed cup of lime and grapefruit and it was SO good, we all went back and got seconds. The lemon and lime flavors were my favorite. They were the perfect combination of sweet and tart.

6. Visit Millennium Park

No trip to Chicago is complete without a visit to Millennium Park. This is definitely one of Chicago’s top tourist destinations and it’s home to the famous sculpture Cloud Gate. Right now, you’re probably shaking your head wondering what in the heck is Cloud Gate? Well, I’ll give you a hint, it’s also affectionately known as The Bean.

Top 6 Things To Do in Chicago: The Bean

Millennium park hosts an array of events each season including: concerts, festivals, and theater performances. If you plan your trip right, you might find enough to do there to spend an entire day exploring and taking in the culture. Just be prepared for crowds and crowds of people everywhere you go.


Number 7 is a bonus for you guys who make it to Chicago at the right time. Go to a Cubs game at the historic Wrigley Field. While we were in Chicago, the Cubs were playing an “away” game against the freaking White Sox at their dumb stadium. But if they would have been playing at Wrigley, we definitely would have splurged on tickets to go to the game. You can tour the stadium anytime, but John and I decided to save our money and put it towards a return trip to the Windy City when the Cubs are playing at home!

Have you been to Chicago yet? What was your favorite thing to do in the city? Let us know in the comments below!

More of Our Excellent City Guides:

Check out Charleston, South Carolina

A First-Timer’s Guide to New Orleans

Check Out Our Other Top Lists Below!

1. Top 7 Things To Do in Santa Fe, New Mexico

2. Top 5 Things To Do in Big Bend National Park, Texas

3. Top 5 Things We’ve Learned After Living in a Van for a Month

Top 6 Things To Do in Chicago

We’re Tiffany and John, a couple of childfree, DIY travel enthusiasts from Montana and we just can’t get enough of life on the open road.

If you’re anything like us, then you feel the same way! We love exploring new places together and finding unique things to do everywhere we go.

Read more about our story here.

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