With the weekends affording many of us time to take a break from our work lives, we must fill them with memories. Whether exploring the parks, spending valuable time with friends and family, or enjoying an event somewhere in Chicago, weekends are designed to be enjoyed!
Luckily, in such a sensational city like Chicago, options are abundant. To ensure you can make the most of your weekend, we’ve rounded up some of the best things to do in Chicago from June 4th to July 6th.
Celebrate the 4th of July
The 4th of July is officially here this weekend, so it’s time to start planning how to celebrate this year. Festivities will include dazzling fireworks, barbecues, rooftop pools, park picnics, and decorations in red, white, and blue!
Lounge by a rooftop pool
Pool season is officially here! From luxurious hotels to member-only clubs, Chicago is brimming with rooftop pools, and finding the right one can be tricky, so here is our complete guide to our favorite hotels in Chicago with rooftop pools you can lounge at this summer.
Sip cocktails at a speakeasy in a secluded lounge
We love the allure of a cool, hidden gem. While there are many spots in Chicago, you should check out upstairs at Nisos this weekend. The Lounge is an alluring, hidden cocktail lounge (hint: look for the bookshelf) tucked away on the second floor of Nisos Prime. The 2,000-square-foot room offers a wondrous, carefree late-night speakeasy.
Go to this wild bingo experience
Check out this bingo experience that’s anything but typical. Bingo Loco delivers a wild night out with confetti showers, epic lip-sync battles, dance-offs, and CO2 cannons—all led by hilarious comedian MCs. Want the chance to win some truly outrageous prizes? Grab your tickets now because they’ve given out cruises, a piano, a giant inflatable flamingo, a microwave, a lawnmower, and even a trip to Vegas at past events!
Check out the Hamptons of the Midwest
Chicago actually has its own romantic and bucolic destination: Harbor Country, haphazardly labeled “The Hamptons of the Midwest.” Harbor Country is a region in Southwestern Michigan. It’s a favored weekend getaway destination for those looking to relish in a tranquil retreat with beaches, bed and breakfasts, and wineries.
Grab Bottomless Brunch
Chicago food is seriously on another level, and nothing makes that more apparent than the city’s endlessly delicious list of bottomless brunch options. This popular weekend activity typically involves breakfast delicacies, bottomless mimosas, and perhaps endless Bloody Marys if you feel extra spicy.
It’s one of the best things to do in Chicago this weekend, centered around festivity and fun. With this in mind, we’ve rounded up a few of the best spots to enjoy an exciting bottomless brunch in Chicago!
Escape the city to a charming town for a weekend getaway
The small town is a storybook setting with historic 1800s architecture that is dazzling as you stroll Main Street, coined “Helluva Half Mile,” which sprawls with more than 125 independently owned business shops. It will make you feel as if you have fallen straight into the scene of an Emily Henry novel.
Dine at one of the best new restaurants
Deciding where to dine on a Friday or Saturday night can be daunting. Whether you’re with a group of friends or having a date night, everyone has an opinion when selecting a restaurant. From arbitrary TikTok recommendations to Instagram reels, narrowing down the Chicago dining scene is easier said than done. That’s why we’ve done it for you with this unequivocal list of the best new restaurants in Chicago you need to try this weekend! Now, let’s hope a reservation becomes available.
Check out LIV Golf and See Good Charlotte perform live!
LIV Golf is returning to the Bolingbrook Golf Club August 8-10, but you can start preparing for the world-class event this weekend! First, the event: it’s a three-day festival-style tournament where 54 of the world’s top golfers compete in a team-based format. Kids under 12 get in free, and there are plenty of options for food, drinks and interactive activities. Plus, Good Charlotte is headlining on August 9. Click here to get your tickets now! They are about to sell out.
📍Location: Bolingbrook Golf Club – 2001 Rodeo Dr, Bolingbrook, IL 60490
🗓️Dates: August 8-10, 2025
