Time out chicago new years eve8/9/2023 ![]() ![]() ![]() Rent a Divvy bike if you want to cover the most ground, and make sure to leave time to stop at one of the many waterfront restaurants. The trail is a popular place for walking, biking, running, and rollerblading. Wander the Lakefront Trail Clayton Hauck for Choose ChicagoĬhicago’s gorgeous Lakefront Trail stretches almost 20 miles along Lake Michigan, offering stunning skyline views and connecting you to many of Chicago’s waterfront neighborhoods, including Edgewater, Uptown, Lakeview, Lincoln Park, South Loop, Bronzeville, and Hyde Park. Check out our outdoor dining guide, with some of the best patios all around Chicago. Enjoy one of the best al fresco weekends with an outdoor brunch on an enchanting garden patio or craft cocktails at a rooftop bar with skyline views. Patio weather in Chicago comes and goes quickly. Their ballpark, Wrigley Field in aptly named Wrigleyville, is one of the oldest and most iconic stadiums in the country - truly a bucket-list activity. The Chicago Cubs will be in town for the holiday, playing the Giants on Monday, Sept. Afterward, spend some time exploring the lively Bridgeport neighborhood. They’ll be facing off at Guaranteed Rate Field all weekend long. The regular season might be winding down, but you still have time to catch the Chicago White Sox play. The popular waterfront restaurants and bars are open for just a little longer, so make your reservations now. It’s the perfect spot to hop on a boat tour, admire the surrounding architecture, and enjoy a drink with waterfront views. Where else can you find an urban canyon filled with delicious food, cocktails, public art, and stunning views? The Chicago Riverwalk is open to enjoy all Labor Day weekend long. ![]() Extreme Thrill Ride with Chicago SeadogĬheck out our guide to Chicago boat tours on Lake Michigan and the Chicago River.Brunch Cruise on Lake Michigan with City Cruises.Architecture Tour on the Chicago River with Shoreline Sightseeing.Chicago Architecture Center River Cruise aboard Chicago’s First Last.Here are just a few boat cruises happening on the water this Labor Day weekend: Choose from informative architecture tours, fast-paced speedboat rides, unforgettable dinner cruises, tiki-themed party boats, sunset and fireworks cruises, and more. Set sail on one of Chicago’s scenic boat cruises on our two sparkling waterfronts. 3 features a 30-mile loop on the iconic road, inviting bikers to enjoy a long or short ride while taking in views of the lake and city skyline. North Coast Music Festival: This annual Labor Day weekend music festival includes electronic music, hip hop and rock acts, plus art installations and food vendors.īike down Lake Shore Drive Bike the Drive on Lake Shore DriveĮnjoy a scenic ride down Chicago’s stunning DuSable Lake Shore Drive, which is shut down to cars just one day each year.ARC Music Festival: This immersive fest in Union Park celebrates house music, a Chicago-born genre, over Labor Day weekend.Chicago Jazz Festival: The oldest of Chicago’s free lakefront music festivals boasts an incredibly diverse lineup in the heart of the loop.This year, the weekend is packed with a diverse line-up of fests - catch a free concert in Millennium Park, dance the night away at a house music festival, and more. You can’t do Labor Day in Chicago without checking out one of the city’s annual music festivals. Check out top events and things to do over Labor Day weekend 2023 in Chicago. Celebrate the end of the season with boat cruises, dinner on a patio, music under the stars, exhilarating live sports, cocktails at the beach, and so much more. Summer in Chicago may be coming to an end, but Labor Day weekend is full of ways to enjoy the final days of sunshine and warm weather. ![]()
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