Your ultimate guide to Chicago

When visiting a city that has so much to see, especially where architecure is concerned,  cefficiency is key. Instead of a walking trail that takes you down Michigan Avenue, State Street and Edgewater Beach, view the landscape from the comfort of one of the best boat tours in Chicago — where there's no chance of taking a wrong turn. Both the Chicago River and Lake Michigan offer unparalleled vantage points for taking in the city’s world-famous architecture and the breathtaking Chicago skyline. From architecture tours and history lessons to straight-up sightseeing affairs, romantic sunset excursions and pirate-themed family fun, there's a Chicago cruise for every groove. All aboard!  RECOMMENDED: 📍 Find more to explore with the best things to do in Chicago🏨 Plan your trip with the best hotels in Chicago 🍹 See more views from the best rooftop bars in Chicago How do we determine the cream of the crop? Our staff picks combine the top, most recent reviews with some of our personal favorites to make sure you get the best deal on the web. Throughout this article, you may notice some affiliate links — these have no influence on our editorial content — we pinky swear. For more information, see our affiliate guidelines.

Chicago is at its best when the sun shines an hour longer, the birds sing a little louder and the breeze off of Lake Michigan is just a bit warmer. This is also when Chicagoans' calendars start to fill up with plans to lounge at some of Chicago's best beaches, gather for a meal on a stunning rooftop or plan time to explore the city's beautiful parks. There are so many things to do outdoors within the city limits, from hopping on a bike trail to free movies in the park. You may even want to escape the city for a breath of fresh air with an adventurous hiking trail or daytrip to what feels like another planet. So if you're up for some fun in the sun, these are our recommendations on the best things to do outside in chicago. RECOMMENDED: The best outdoor bars in Chicago

There are few better ways to beat the heat in Chicago than by hitting one of the many sandy beaches along the shores of Lake Michigan. From the North Shore to the South Shore, there are plenty of options to choose from, whether you’re looking for a chill day of sunbathing, want to take in the skyline from a kayak or paddleboard, or love to get competitive with a game of volleyball. Make the most of summer in Chicago by packing a towel, snacks and some sunscreen and heading out early to secure a spot. If you’re really looking for vacation vibes, you can visit a waterfront restaurant serving drinks and hosting live music. Just be sure to check the water conditions before you go and consider visiting a public swimming pool if the lake is off limits. Note: Chicago's summer beach season runs through Labor Day. RECOMMENDED: Full guide to the best things to do in ChicagoThe most romantic places to stay in Chicago

From Andersonville to Woodlawn, neighborhoods across the city bring in Midwestern vendors at the best farmers markets in Chicago.

Nothing beats a Chicago rooftop. When you're looking for something a little more filling than cocktails at rooftop bars in Chicago, turn your attention to the city's top rooftop restaurants, where dinner comes with a side of amazing skyline views. We've rounded up rooftop dining options to suit every mood, including tucked-away rooftop terraces, sunny outdoor brunch spots and bites from some of the best restaurants in Chicago. Gloomy weather in the forecast? Several of these spots also offer indoor dining or covered patios to keep you safe from the elements while you feast. So get ready for a sky-high meal at the best rooftop restaurants in Chicago.  RECOMMENDED: The best outdoor restaurants in Chicago Updated April 2026: One of the great joys of summertime in Chicago is spending time outside, and what better way to do that than dining on a rooftop? This ranking of the best rooftop restaurants in Chicago is your guide to the al fresco spots that are actually worth your time—and worth the struggle to get a table. Popular destinations like Aba and Cindy's are packed on sunny days, but if you're willing to wait, you won't regret it. There are also quieter spots on the list, like Miru, that are equally impressive and less crowded. All of them, though, offer top-notch cuisine and city views that remind us why this city is so great. 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.

Chicago's motto is "City in a Garden," and our public green spaces live up to such a lofty name. With more than 600 facilities throughout the city, the Chicago Parks District boasts something for everyone, whether you're looking for a tiny neighborhood playlot for the kids or a vast swath of green space. Chicago parks are more than just places to work out, ride your bike or play tennis—they also offer plenty of cultural programming, such as summer festivals or outdoor movies. Most importantly, these Chicago attractions provide a space to relax and momentarily forget that you're in the middle of a large city filled with people, buildings and cars. Not sure which Chicago parks you should visit? Leaving aside Chicago beaches (unfair advantage, honestly), these are some of our favorite spots in the city. RECOMMENDED: The best places for hiking near Chicago