When the snow finally melts, Chicago, also known as “The Windy City,” becomes the perfect destination for a spring weekend. Chicago is America’s third largest city and such a great place for a weekend break.

I went to Chicago on a weekend with no expectations whatsoever and I got that wow-feeling immediately from the skyline, the amazing blue color of Lake Michigan, all the good food and the welcoming feeling. I felt right at home, loved every minute of my spring trip and just discovered more things to do in Chicago as I walked around the city. Here are 22 fun-filled activities and eateries.

Try These Great Things to Do on a Spring Weekend in Chicago

Activities, Sightseeing, Shopping

Here are my favorite activities, plus places to shop and visit.

1. Millenium Park

Millennium Park is perfect for strolling and looking up at skyscrapers. Take a selfie with Cloud Gate or “the kidney bean” as people call it.  It’s made of 168 polished stainless-steel plates and its reflection captures the skyline. When the weather is good, you can enjoy concerts, yoga, and movie nights there.

Don’t miss the Crown Fountain designed by Jaume Plensa. Two glass brick towers covered in lights face each other across a shallow reflecting pool. The towers show different faces of people from Chicago and every five minutes, the person on the screen squirts nearby visitors with water.

2. Lincoln Park

Lincoln Park 2045 N Lincoln Park W, Chicago

Lincoln Park is Chicago´s biggest public park where you can stroll for hours. There is also an outdoor zoo, a conservatory and a cultural centre. When you need to rest your legs head over to RJ Grunts for delicious milkshakes and sweet potato fries.

3. Chicago Lakefront Trail

Chicago Lakefront Trail is a 29 kilometre-long trail that starts off at Ardmore Street and finishes at 71st Street. As well as walking, you can go running, rollerblading or biking. I recommend renting a bike for a couple of hours and feeling the wind in your hair. The skyline is breathtaking!

4. Wicker Park

Wicker Park 1425 N Damen Ave, Chicago

Wicker Park is one of my favorite neighborhoods in the city. Vintage shops, hipster restaurants, art galleries, chic wine bars and a lot of street art. Visit Myopic Bookstore with three floors of books from floor to ceiling and Vitru that sells jewelry and tableware made by local designers. This is one of those neighborhoods that has been influenced by artists over the years.

5. River Cruise

The best way to get to know Chicago is from the river. Join a boat tour from Michigan Avenue, sit back and enjoy the ride. There are a lot of different tours to choose from. I recommend the Architecture Cruise which is just over an hour long. You get to see the city, know a little bit more about its history and see all its best sites. Enjoy Chicago’s bridges, skyscrapers, townhouses and all the great photo opportunities the city has to offer.

6. Willis Tower

Willis Tower 233 S Wacker Dr, Chicago

Willis Tower was the tallest building in the world for a long time and is still in the top 25. Get the Experience ticket which allows you to skip the line and enjoy the view from Skydeck, 412 metres above the ground. For the full experience, head over to the glass balcony where you can stand in a glass box and get the feeling that you are floating outside the building as you look 72 floors straight down.

Good advice before you visit Willis Tower: Visit early in the morning or later in the evening (sunset is spectacular) and remember to have a look at the interactive exhibits on the way to the elevators to learn more about the city.

7. Chicago Farmers Market

Chicago Farmers Market, Daley Plaza, Chicago

Chicago Farmers Market is the best market in town for fresh fruit and vegetables, flowers, homemade bread, plants and more. At Daley Plaza, you will find Chicago’s longest-running farmers market. The Market is open May – October.

8. Navy Pier

Navy Pier is open all year round and is free of charge. The best time to visit is during spring, summer and fall, and the place has waterfront access to Lake Michigan. There’s a carousel, Ferris wheel, maze experience, children’s museum, beer garden and restaurants. There are bands playing along the pier. This is the perfect place to snap that photo with you against the skyline.

9. Magnificent Mile

Magnificent Mile, Chicago River to Oak Street, Chicago

Magnificent Mile is the avenue for shopping, entertainment, restaurants, hotels, dazzling architecture and basically everything you need in a big city. You’ll find elegant and luxurious shops, as well as more affordable brands such as Zara, Nike and H&M. As you walk the avenue, enjoy the view of the city’s most famous buildings like Hancock Tower, Tribune Tower and Wrigley Building.

10. Chicago Riverwalk

Chicago Riverwalk is maybe the most Instagram-friendly walk in the city. With a floating garden, amazing architecture, cocktail bars, and cafés, this is where you can spend hours just soaking up the atmosphere. Your weekend in Chicago is not complete without this.

11. Garfield Park Conservatory

Garfield Park Conservatory , 300 N Central Park Ave, Chicago

Garfield Park Conservatory is the place to visit if you love plants. This is a tropical garden under a glass roof, open 365 days a year and free of charge. Bring your walking shoes because this place is big. The conservatory is divided into different rooms to provide different climates for different plants. You get a feeling of being in the tropics right in Chicago. In the summer, there are also other gardens outside.

Where to Eat in Chicago

Continuing with my list of the best things to do during a spring weekend in Chicago, there is plenty of delicious food you won’t want to miss!

Best Breakfast Spots in Chicago

Here are suggestions for where have breakfast in Chicago.

12. Wildberry Pancakes

This is the spot for a huge weekend breakfast in Chicago. The portions are enormous, and they have the best selection of pancakes in town. I recommend mocha coconut coffee and apple pecan pancakes.

13. Lou Mitchell´s

565 W. Jackson Blvd, Chicago

Lou Mitchell´s is a classic breakfast place and is just at the beginning of Route 66. While waiting in line, the staff will hand you fresh donut holes. You’ll find big portions, awesome corned beef hash and good waffles. Go here for an early breakfast and then just cross the street to enter the Willis Tower.

Lunch and Dinner in Chicago

Make sure to eat your breakfast early so that you’re hungry by lunchtime. You won’t want to skip it!

14. Chicago Dog House

You can’t eat in Chicago without having a hot dog. Some of the best hot dogs in town are served in the Chicago Dog House. They serve the original hot dog, but you can also spice it up or get meats like rabbit, duck or alligator.

15. 3 Arts Club Cafe

1300 N Dearborn Pkwy

This is an absolutely beautiful restaurant with gorgeous furnishings on each level. The restaurant is in a historic building in the Gold Coast complete with a central fountain, high ceilings, large windows and chandeliers. This place is very popular, and they don’t take reservations. Put your name on the list, have a wander around the neighbourhood and they will text you when your table is ready. Great lobster roll and kale Caesar salad.

16. Big Star

531 N Damen Ave

Big Star is right by Wicker Park and the atmosphere is awesome. Enjoy the first day of spring on their patio with such a good vibe and music playing. They have a great selection of craft beers and tacos. Why not try the carrot taco? It’s awesome!

17. Girl and the Goat

809 W Randolph St

Chef Stephanie Izard offers up a very interesting and decadent menu! Try the green beans, lamb ribs and pork shank. All dishes are served family style and perfect for sharing. Very friendly staff and don’t miss out on buying the chef’s own cookbook.

18. Etta

1840 W North Ave, Chicago

Good restaurant for pizza and pasta. The pizzas from the wood oven are awesome and don’t miss their ricotta balls. The main floor is an open space floor plan. Upstairs provides a more cozy and intimate setting.   

Where to Drink in Chicago

Here is a list of my recommendations on where to drink in Chicago.

19. Cindy’s Rooftop

The bar at Cindy’s Rooftop is located on the top of the Chicago Athletic Association Hotel. From the balcony, you can enjoy perfect cocktails and a nice view over Lake Michigan and Millennium Park. Cindy’s Rooftop has blankets and a fire pit so you can enjoy the rooftop even if the weather isn’t that warm. Try to get here early to get a good seat with the best view.

20. Lost Lake

3154 W Diversey Ave, Chicago

This tropical cocktail bar is very popular especially on Saturdays, so make sure you get here early. They open at 5 pm. Drinks are large and colorful, and their Tiki cocktails and vibe is one of a kind. A tropical paradise right in the city.

The Best Donuts and Popcorn in Chicago

For more recommendations on where to eat in Chicago, check out these popular places for delicious snacks!

21. Stan’s Donuts

Perfect donuts and good coffee too. A great weekend treat is their peanut butter filled chocolate donut or the toffee crunch cake donut. They offer so many different flavors it’s hard to choose and they also do gluten-free. You can find Stan’s Donuts in a few different places in the city like Magnificent Mile, Wicker Park and Millennium Park.

22. Garrett Popcorn Shops

625 Michigan Avenue

Don’t leave Chicago without visiting Garrett Popcorn Shops in the heart of Chicago’s Magnificent Mile. The handmade gourmet popcorn comes in different flavours like caramel crisp, cheese corn and macadamia caramel crisp. You can smell the popcorn all around the block.  Try the Garrett Mix that is the perfect blend between sweet and salty. Well worth queuing for and best when they are warm.

Best Things to Do on a Spring Weekend in Chicago

So, there you have it – some of my top things to do on a spring weekend in Chicago! Hope you have a wonderful time.

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by Towe Ahlin