Our favorite thing about Chicago is that it has all the big city, metropolitan amenities while maintaining the outdoor spaciousness of the wide-open outdoors. There is an abundant amount of fun things to do both inside and outside in Chicago! But because it’s easier to maintain social distancing in the great outdoors, we’re sharing our ten favorite things to do outside in downtown  Chicago. 

Note: Some attractions and businesses may be closed or are operating at a limited capacity. It’s always best to check their official site before visiting. 

Our Favorite Things To Do Outside in Downtown Chicago

  1. Enjoy a Chicago-Style Hot Dog at the Art Institute of Chicago Garden
  2. Taste Chicago’s History on the Chicago Favorites Walking & Food Tour
  3. Go Kayaking on Lake Michigan
  4. Embark on an Outdoor Sculpture Excursion
  5. Set Out on an Architecture Safari of Downtown Chicago
  6. Walk Along Lake Michigan (or Rent a Bike)
  7. See a Movie at an Outdoor Drive-In Theatre
  8. Celebrate the Chicago Cubs on a Rideabout to Wrigley
  9. Discover Outdoor Dining Options in Chicago
  10. Get Dazzled by the Lincoln Park Zoo Lights
  11. Ice Skate at the Maggie Daley Park Skating Ribbon


Enjoy a Chicago-Style Hot Dog at the Art Institute of Chicago Garden

Garden image by Arvell Dorsey Jr

The Art Institute of Chicago has some of the most iconic paintings ever created: American  Gothic by Grant Wood, An Afternoon on the Island of la Grande Jatte by Georges Seurat, and  Water Lilies by Claude Monet. The Art Institute also has a lovely (and free!) outdoor garden right next to Millennium Park. You don’t have to go into the museum to enjoy this pastoral haven in the heart of downtown Chicago. It’s the perfect place for the whole family to sit down and nosh on some Chicago-style hot dogs from a local street vendor!

Taste Chicago’s History on the Chicago Favorites Walking & Food Tour

One of the best ways to explore the history and taste of downtown is on a Chicago food tour! This all-age Chicago Favorites walking food tour will introduce you to the history of Chicago through its most classic foods: deep-dish pizza, Italian beef, and the Chicago-style hot dog. You’ll also visit all the must-see downtown sites including the Chicago Theatre, the Magnificent Mile, and the  Bean. It’s guaranteed to check off at least five items from your visiting Chicago bucket list! And if you’re a foodie, check out the best Chicago food tours blog for more ideas!


Bobby’s Bike Hike: Chicago’s Favorites Walking Food Tour in Downtown Chicago (Italian beef sandwich)


Go Kayaking on Lake Michigan

Downtown Chicago is the gateway to so much fun, from the arts in the city to water activities on the lake. Rent a kayak and explore Lake Michigan from downtown Chicago. Paddle in a single kayak, or go double in a tandem kayak. Whether you’re a pro or you’re just beginning, there’s a community here to support you and offer paddling instructions to get you out and having fun.

Spend time on Ohio Beach, then head out on a kayak tour of Chicago with guides from Bobby’s. Have fun cooling off in the water on a hot day and learn more about the important role the lake and river play in Chicago’s history.


Embark on an Outdoor Sculpture Excursion 

Photo by Kris Lucius

You don’t have to go inside a museum to experience the star-studded cast of Chicago’s public artwork scene. From Pablo Picasso to Sir Anish Kapoor, downtown Chicago is full of famous works. For a low-key exploration of the city, go on a photographic sculpture excursion! And unlike your typical art museum, your pets are absolutely welcome to get cultured as well.

Set Out on an Architecture Safari of Downtown Chicago 

Photo by Diego Delso

Unlike some cities where the architecture feels relatively uniform (not naming names here, New  York), Chicago’s architecture is a diverse affair. The gold-tipped Carbide and Carbon building that represents a Champagne bottle. The neo-Gothic Tribune Tower. The petaled Marina City,  home of the most terrifying parking deck in existence. There are so many iconic buildings in  Chicago, it’s no wonder Hollywood likes featuring them in films. If you’re looking for fun things to do outside in Chicago, try to visit each building on this mapped list of Chicago’s most iconic buildings.

Walk Along Lake Michigan (or Rent a Bike in Downtown Chicago)

Lake Michigan is Chicago’s best, worst-kept secret. Many outsiders don’t realize that Chicago is a beach city! In addition to the wonderful beaches you can swim and fish at, the Lakefront Trail is an 18.5 mile stretch of trail that’s perfect for running, dog walking, and biking. Don’t have a  bike? You can rent a bike by the hour, half-day or monthly. 


Bike Rentals in Downtown Chicago from Bobby’s Bike Hike


See a Movie at an Outdoor Drive-In Theatre 

Photo by distelAPPArath

One thing we really miss during the pandemic is going to the movies. Thanks to Chitown movies, you can now safely visit the cinema, outside in downtown Chicago, drive-in style. Now you can provide running commentary on the plot holes without bothering strangers! The venue is located in Pilsen, and you can purchase delicious food like tacos, wings, and frozen mangos in addition to the standard movie theatre snacks.

Celebrate the Chicago Cubs on a Bike Rideabout to Wrigley 

If you’re looking to leave the Downtown Loop, check out our Bobby’s Bike Hike Ridebout to Wrigley. Starting down at the Magnificent Mile near Navy Pier, you’ll ride north to Wrigleyville, home of the Chicago Cubs. Along the way, you’ll feel the Lake Michigan breeze as you cruise up the Lakefront Trail and then visit Lincoln Park. Worried all the biking will make you hungry? Lunch is included in the form of a classic Chicago-style hot dog. This all-ages bike tour is designed for local Chicagoans, but visitors love it too!


Bicycle Tour around Wrigley Field with Bobby’s Bike Hike


Discover Outdoor Dining Options in Downtown Chicago

Photo by Shelby L Bell

We know what you’re thinking… outside dining?! And winter is coming? With Covid came the need for innovation, and ever since the 1893 World’s Fair, Chicago’s had that skill in abundance! From heated tents to kotatsu tables, outdoor dining in Chicago has been forever changed. In fact, we anticipate it’s here to stay! For a list of restaurants with outdoor dining options check out Choose Chicago’s Outdoor Dining in Chicago: Heated and Covered Patios Open Right Now. It’s always best to call the restaurant to confirm dining options.

Things To Do in Downtown Chicago During The Winter Months

Get Dazzled by the Lincoln Park Zoo Lights 

Photo by Magnus Manske

The Lincoln Park Zoo is an annual Chicago favorite for locals and tourists alike, especially since it’s free! During the winter months, LP Zoo unveils its most popular attraction: The Zoo Lights. They have hundreds of glittering, festive displays guaranteed to dazzle you no matter your age. Unfortunately, the only animals allowed at the Zoo are those who already live there, so you’ll have to leave the dog at home. Though the zoo is free, the zoo lights exhibit may have a cost.

Ice Skate at the Maggie Daley Park Skating Ribbon 

Photo by ferobanjo

Maggie Daley Park always has a plethora of activities to choose from, and it’s arguably the most family-friendly park in Chicago! During the warmer weather, you can rock climb, play tennis, and enjoy a round of mini-golf. Starting late November, it transforms into our favorite ice skating spot in Chicago. Unlike the traditional-style rink in front of The Bean, this path is a looping ribbon, so you really feel like you’re traveling somewhere. 

Have you enjoyed any of these things to do in downtown Chicago, or do you have other recommendations for things to do outside in Chicago? Let us know in the comments below!