Your ultimate guide to Chicago

Sometimes, we all need a change of scenery. It only takes a short day trip to add a little variety to your routine—and even better if it’s a one-of-a-kind experience. You don’t have to fly across the globe or even spend an entire weekend away to relish in the Midwest's quirks. Chicago’s surrounding regions boast countless family-friendly getaways, wineries and nature-based adventures, like hiking and camping, for anyone looking to escape for a day. So whether you're in search of cool and interesting museums or looking for something truly remarkable—say, Egypt on the side of an Illinois highway or a slice of Venice in the Crossroads of America—these are the best unique day trips from Chicago. RECOMMENDED: The best lakefront Airbnbs near 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

The annual Oktoberfest celebrations mark the arrival of fall, but even if you can't make it to Munich, plenty of Chicago institutions are throwing bustling, German-themed parties to ring in a new season. From special tappings at Chicago breweries to carnival rides outside neighborhood churches, we've gathered some of the best parties and events during Oktoberfest in Chicago, taking place at amazing restaurants, bars and even zoos. Break out those dirndls and lederhosen and prepare to say "Prost"! What is Oktoberfest?  Oktoberfest is a multi-week beer festival and fair held in Munich, Germany. Originally conceived to celebrate the marriage of Bavarian King Ludwig I and Princess Therese of Saxony-Hildburghausen in 1810, the festival has since evolved into a public event and one of the most important cultural symbols in Bavaria, drawing millions of attendees from across the world each year.  When is Oktoberfest in Chicago? Although Munich's Oktoberfest takes place this year from September 19–October 4, Chicago's celebrations generally take place anywhere from mid-September to late-October.

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.