The City of Chicago has 100 neighborhoods, 8 major league sports teams, 36 annual parades, 450 live performance venues, 600 parks, 29 beaches, and over 7,300 restaurants.
If you’re visiting Chicago in the Summer, the question isn’t “will there be anything to do?” but “how on earth do I choose?” The options can be overwhelming, but there are infinite possibilities for customizing your trip itinerary! What will you decide to do when you arrive in the Windy City looking for a good time?
This guide should make your decision much easier! It includes some unique things to do in Chicago once the weather starts getting nice. Keep reading to begin mixing and matching experiences to create an urban adventure that you’ll never forget!
1. Get on Board a Booze Cruise
While you’re in the Windy City, odds are good that you’re going to stop by the world-famous Navy Pier. Once you’re there, why not leave the bustling urban city behind and kick back with a cocktail? A private booze cruise is a great way to see the city from a distance as you relax with friends or family, right on the water.
You won’t have to choose a DD or worry about safety. The captain will keep everything under control as you enjoy the Chicago sights and lights from onboard the boat! Check out this awesome booze cruise near me to get started.
2. Stick To the Shore
If you’d rather bask in the sand while you’re visiting Chicago in the Spring or Summer, there are plenty of beaches accessible from the city! You’ll have your choice of water sports, like jet skiing or kayaking, or you can chill out with a good book.
A few of the best Chicago beaches include:
- Oak Street Beach
- Foster Beach
- Shore Club Chicago
- North Avenue Beach
Visiting the beach while you’re in a big city like Chicago will add a sense of variety to your vacation. You don’t need to stick to the hustle and bustle to keep things interesting!
3. Go On an Art Crawl
Distinctive Chicago architecture and striking public art is everywhere in the city! You can see it all when you organize an art crawl and hit all of the most striking landmarks in one day.
Start with Cloud Gate then meander The Loop to see masterworks by Marc Chagall and Pablo Picasso.
4. See Stars Under the Stars
Every Tuesday in the Summer you can visit Millenium Park to catch a free film screening under the stars. Pick up a takeout picnic from one of the nearby restaurants and dine on the Great Lawn.
No matter where you sit you’ll have an awesome view of the 40-foot LCD movie screen!
5. Rock Out at Famous Chicago Festivals
Will you be in town for one of Chicago’s major outdoor music festivals? Lollapalooza, Riot Fest, and Pitchfork Music Festival all take place right in the Windy City!
Best of all, they tend to coincide with the Windy City Smokeout, so you’ll eat well while you take in the tunes!
6. Visit the Museum
If you’re stuck with bad weather, there are still plenty of things to do indoors in Chicago! One of the most fun things to do is to visit one of the city’s many museums to take in the culture.
Some of Chicago’s best museums include:
- The Field Museum
- The Shedd Aquarium
- The Art Institute of Chicago
- Chicago History Museum
- The Museum of Contemporary Art
- The Museum of Contemporary Photography
- The Smart Museum of Art
- The Oriental Institute Museum
- The Adler Planetarium
- DuSable Museum of African American History
- The Peggy Notebaert Nature Museum
- The National Museum of Mexican Art
You could spend your entire visit hopping from one museum to the next! The special exhibits change seasonally, so make sure to find out what will be new this summer!
7. Enjoy Outdoor Dining
You already know that Chicago is home to 7,300 restaurants (and counting). Why not choose an eatery with outdoor seating to enjoy the weather and the cuisine at the same time?
In the Covid era, outdoor dining options have expanded, and you can find almost any cuisine right on the busy Chicago streets!
8. Hit the (Bike) Trail
Chicago is a bike-friendly city, and you can enjoy all there is to see on two wheels. For a relaxing day out, visit one of Chicago’s many scenic bike trails.
Wave to Lake Michigan while you ride along Lakefront Trail, or travel to the Wisconsin border on the Des Plaines River Trail!
9. Have an Explosive Fourth of July
If you happen to be in Chicago around Independence Day, make sure to catch the big fireworks down at Navy Pier. You don’t even need to be in Chicago on the fourth itself to catch the explosive display.
You can catch twice-weekly fireworks from Memorial Day weekend through Labor Day weekend.
10. Check Out Garfield Park Conservatory
If your trip to Chicago is a substitute for a tropical getaway, why not have it both ways? The Garfield Park Conservatory boasts eight distinct tropical gardens.
All you need to do is make a reservation online and you can pretend you’re on an island in the sun!
11. See the Whole City at Once
If you are only in Chi-town for a few days, you probably want to see a lot of the city quickly! Check out Chicago 360, an observation deck 1,000 feet in the air.
Not only will you see all of Chicago, but you can also catch glimpses of Indiana, Wisconsin, and Michigan on a clear day!
12. Walk the 606
New York City shouldn’t get to have all the fun! Chicago’s answer to the NYC Highline is the 606. It’s a three-mile elevated rail line that has become a park where you can run, bike, walk, or check out some awesome art.
Have a Blast in Chicago in the Summer!
Your trip to Chicago in the summer doesn’t need to look like anybody else’s! Take a walk on the wild side and check out all of the unique options above. You can mix and match your dream itinerary and curate a Windy City adventure like no other!
Are you looking for more tips for planning your awesome trip? Check out the rest of the blog for more travel inspiration for jet setters, weekend warriors, and everyone in between!