Things to Do in Chicago in May
A Guide to Chicago Events in May, From Bar Crawls and Beach Festivals to Zoo Nights and Riverwalk Parties
Chicago fully shifts into spring mode in May. The weather improves, patios open up, and the city starts hosting outdoor events again. From bar crawls and food festivals to beachside tastings and baseball pre-games, there’s a lot happening across the city.
If you’re looking for things to do in Chicago in May, here’s a breakdown of events and activities worth planning around.
Late Spring Kickoff Events (End of April)
Before May officially starts, a few late-April events are worth including, especially if you’re visiting around that transition period.
One of the more unique options is the Adults Night at the Trampoline Park | 21+ Only | Jump Then Enjoy a Beer!. It’s exactly what it sounds like: a 21+ session where you can jump, then stick around for drinks. It’s a different pace compared to the usual bar scene and works well as a casual group activity.
Architecture Boat Tour
If you’re planning a trip to Chicago this May, one activity worth adding to your list is an architecture cruise. The Chicago River gives you a completely different view of the city, with guides explaining how the skyline came together over time. You can check out the 90-minute architecture boat tour here. It runs along all three branches of the river and is one of the easiest ways to fit a major Chicago experience into your itinerary.
Cinco de Mayo Events and Bar Crawls
Cinco de Mayo is one of the busiest weekends in May, especially for bar crawls and themed parties across the city.
The Cinco de Mayo Bar Crawl Chicago — The Ultimate Fiesta is one of the main events, bringing together multiple bars with drink specials and a full-day party setup.
If you’re heading to Wrigleyville, the Cinco de Mayo Cubs Pre-Game Party at the #1 Cantina in Wrigleyville combines the holiday with game-day energy, making it a solid option before heading into Wrigley Field.
For something that runs beyond just Cinco weekend, the Cubs Pregame events continue throughout the month and are a consistent choice if you’re planning around a game.
These are some of the more popular Chicago events in May, especially if you’re looking for a social, high-energy atmosphere.
Outdoor Parties and Riverwalk Events
As temperatures rise, more events shift outdoors, especially along the river and near the lake.
The Bottomless Mimosas on the Riverwalk – Every Weekend in Chicago is a simple but popular option. It runs regularly and offers a more relaxed daytime setup compared to bar crawls.
At the lakefront, the Tropical Cocktail Fest on the Beach – Cocktail Tasting at North Ave. Beach brings together drinks, music, and a beach setting. It’s one of the clearer signs that summer is getting close.
Another similar option is the Wine Fest on the Beach – Wine Tasting at North Ave. Beach, which leans more toward tastings than a party atmosphere.
If you’re thinking about things to do in May in Chicago that take advantage of the weather, these are easy choices.
Food, Drink, and Themed Crawls
Chicago doesn’t hold back when it comes to themed events, and May has a few that stand out.
The Chicago Pickle Fest: Live Bands, Beer and Everything Pickle! is one of the more unusual festivals, combining food, drinks, and live music with a very specific theme.
For something more Chicago-specific, the The Malört Crawl: Tix include Entry, a T-Shirt, Buffet & 2 Shots of Malört leans into the city’s well-known liquor. It’s not for everyone, but it’s definitely a local experience.
These kinds of events are part of what makes up the best things to do in Chicago in May, especially if you’re after something less typical.
Unique Nights Out in Chicago
If you’re looking for something outside the usual bar or festival setup, there are still a few standout options.
The Saturday Night at the Zoo – An Adults Only Evening at Lincoln Park Zoo offers after-hours access to the zoo with drinks, music, and a more relaxed crowd. It’s a good alternative if you want a night out that isn’t centered around bar hopping.
May is when Chicago starts to feel active again. Outdoor events return, the lakefront picks up, and weekends fill quickly with festivals and parties.
If you’re planning what to do in Chicago in May, it helps to decide early whether you’re more interested in bar crawls, food events, or outdoor experiences. Many of these events sell out or increase in price as the date gets closer.
For a different perspective of the city, it’s also worth adding a Chicago River architecture boat tour to your plans. It’s one of the easiest ways to see the skyline and works well alongside the more social events happening throughout the month.
Whether you’re visiting for a weekend or building out a longer trip, May offers a solid mix of events, weather, and activity across the city.