chicago in may

Chicago in May

Spring has sprung, and summer is just around the corner. That big yellow ball in the sky isn't so shy anymore. That's right y'all, it's May. Time to shuffle off the light jackets and risk it in just a t-shirt or summer dress. Whether you're hitting the Windy City for a vacation, or a resident wondering how to spend the newfound warmth, never fear! This list caters to you all. Scroll down, and find out what you shouldn't miss in Chicago in May.


  • Skydeck Chicago
  • River Cruises
  • Navy Pier funfair
  • Bike rides
  • The Zoo
  • and more!

Chicago in May: What to Expect

May is when temperatures will start to climb. Generally, you'll find tops of around 68-70°F, or 20-21°C, and dips of around 50-51°F, or 9-10°C. So, pack some lighter clothes for the days, and some warmer jackets and sweaters for the nights. There's a chance of rain too, so pack your best umbrella, just to be safe.

Chicago in May: What to Do

Image of Shoe, Sneaker, Female, Girl, Person, Teen, Child, Running Shoe, Urban,

Skydeck Chicago

Looking for thrills, buddy? How about heading up to the 103rd floor and overlooking the city at over 1,300ft? If that sounds like just the ticket, then check out Skydeck Chicago! Formerly the Sears Tower, Skydeck gives you amazing views across the city and beyond. In fact, you can see four different states from the viewing platform! Spot key Chicago landmarks, and if you dare, head out onto The Ledge, a see-through, glass-floored platform. See the city right beneath your feet. Not for the faint of heart, but if you've already made the journey up to the top, why not go the extra step? We dare you. Then, when you're done, ride the Multimedia elevator all the way down to terra firma, and learn about landmarks as you pass them.

Shoreline Architecture River Cruise

Do you like water? Not just inside your body, but outside too? Does the thought of riding Poseidon's waves while seeing some sweet buildings get you giddy? Well, check this out. Hop aboard a Shoreline Architecture River Cruise and do just that. Chicago in May is the perfect time to catch a ride. The city has heaps of interesting architecture to see, including works from building men like Goldberg and van der Rohe. Plus, you'll learn about the Great Fire in the 19th century that helped shape the metropolis it has become today. Make sure you take some sweet snaps for your social media, so people think you're cooler than you really are. Learning and boats - does it get much better than that?

Image of Water, Waterfront, Amusement Park, Ferris Wheel, Fun, Boat, Vehicle, Cityscape, Urban,

Navy Pier

Do you like rides? Are you looking for an exhilarating experience in the city? Then you're looking for none other than Navy Pier. This 50-acre seaside locale is one of the biggest tourism draws in Chicago. Perhaps the pier's biggest attraction is the Centennial Wheel, a colossal Ferris Wheel that towers over the boardwalk. Rising to over 200ft at its peak, you'll get amazing views all the way to Lake Michigan. And, if those pesky clouds show their grey faces, never fear, as each gondola is a closed unit. On top of all that, there are plenty of other rides to try out, bites to eat, and drinks to wash it all down. Pick up a souvenir while you're at it.

Stop by the Zoo

Why not make the most of the May weather by visiting the zoo in Chicago? Lincoln Park Zoo is a wonderland of animals, with thousands to see and meet. There's the Sea Lion Pool where, shock horror, the sea lions hang out. Or, if you like your mammals landlocked, there's the Center for African Apes, with an assortment of apes and gorillas to see. Then, head into the lion's den at Kovier Lion House, which houses more big cats than you could shake a paw at. Beyond that, you can take a cruise of the South Lake Lagoon, or check out some of the rides. The Lionel Train Adventure is perfect for kids, taking passengers on a trip to explore the surrounding woodland. There's also the Endangered Species Carousel, where riders can hop aboard nearly 50 replicas of endangered animals and help raise awareness of their plight. Then, grab a bite at the cafe, or pick up a stuffed animal for the little one.

Image of City, Urban, Cityscape, Nature, Outdoors, Scenery, Person, High Rise, Water, Waterfront, Bicycle, Vehicle, Landscape, Metropolis,

Bike and Roll

Want to see the sights in Chicago, but make the most of the May weather? Then hop on a two-wheeler and get some exercise while you're at it! Hire a bike, and go exploring. Glide beside Chicago's lakefront, discover the city's many trails and green lanes to avoid traffic, and see all the city's wonders while breathing in that great fresh air. Bring some food and a few drinks, find a spot to settle, and put together a mid-ride picnic. A great way to spend a sunny day in the windy city.

Play ball

If you're a sports fan, you may have heard of the game they call 'baseball.' One person throws a ball, the other hits it with a bat, and then everyone runs around trying to catch it. That about sums it up. Well, if that sounds like you, then you'll be well aware of the Chicago Cubs. A trip to their stadium at Wrigley Field might appeal to all sports fans, as the atmosphere is notoriously infectious. And not in the mask-wearing, 6ft apart way. This century-old ground is home to baseball games throughout the year, so why not check one out and see what all the fuss is about?

Image of Vegetation, Jungle, Nature, Outdoors, Land, Rainforest, Tree, Adult, Female, Person, Woman, Garden, Indoors, Male, Man,

Get flowery

Fancy yourself a bit of a Greenfingers? Then you might be interested in a visit to one of the country's biggest and best botanical gardens! The Garfield Park Conservatory houses thousands of flora beneath its glass dome, and in May, it's the location of the 2022 Spring Flower Show. So if you want to see some award-winning tulips, daffodils, and other flowers you know and love, go check it out!

Relax and see the city

If you want to give those dear legs of yours a rest, why not hop on a bus and get a tour of the town? A Gray Line Chicago Grand Tour takes you around all of the city's biggest landmarks, including Orchestra Hall, Lake Point Towers, and Lincoln Park Conservatory, all the way to Grant Park. You even have the opportunity to hop off and go exploring at certain points, as long as the bus isn't delayed!

And that's everything you need to know about Chicago in May!

Love this article? Why not share it:

Buy with confidence

Free cancellation

Plans can change, we get it. All non-activated passes are eligible for a refund within 90 days from your purchase date.

Find out more


Confused? We're here to help!

See our FAQs

We're kind of popular, but don't just take our word for it.

Have a 5% discount, on us!

Sign up to our newsletter and receive exclusive discounts, trip inspiration and attraction updates straight to your inbox.

  • Thick check Icon