Things to Do

The best spots for outdoor dining in Chicago show off all the beauty the city has to offer.

Sometimes, we all need a change of scenery.

Many of the Chicago's best bars don’t open until 5pm, but that doesn’t mean you have to wait until sunset for a drink. Rooftop bars and sprawling patios are ideal for leisurely afternoons with cold beers and refreshing cocktails, while sports bars offer a place to catch the game alongside fellow fans. Some of these spots also serve brunch so you can start the day with mimosas and Bloody Marys. Whether you're off work or making the most of a Sunday Funday, these bars are our favorites for day drinking in Chicago. RECOMMENDED: Discover the best beer gardens in Chicago Updated August 2026: The latest additions include Lakeview's Long Room, a bar serving both beer and coffee. Also joining the list are the Albion Manor, an English pub, and Lottie's Pub, a classic neighborhood watering hole in Bucktown. Time Out has also instituted a sitewide change in review policies. Our food and drink venues included in guides now have star ratings, with five stars corresponding to “amazing,” four to “great” and three to “good,” and we’ve also standardized how most listings are structured. For more on our new policies, feel free to check out how we review at Time Out.

Nothing screams summertime Chi like admiring the impressive skyline views with a drink in hand.

There are plenty of activities around the city that don't cost a penny.

Don't have to spend a fortune to visit the best museums

A truly great flea market trip can take your weekend to the next level.

Before the city warms up, squeeze in some much-needed rest and relaxation.

Experience art, history and science and these well-respected cultural institutions.