In Chicago for the weekend? Looking for ideas of what to do in the Windy City? We’re here to help! With so much to do, and all of it in a couple-mile radius, Chicago is the perfect city for a quick getaway. Whether you’re looking to be moving and grooving from sunup to sundown or unwind with a relaxing weekend, you’ll find everything here for your ideal weekend escape.
For lodgings, try to choose a hotel downtown, either near The Loop, Magnificent Mile, or River North. This will put you within easy walking distance to some of the city’s best activities. And while you’re exploring our wonderful town, we’re certain you’ll work up an appetite. Thankfully there is no shortage of restaurant and eatery options. Whether you’re craving a slice of deep dish (Giordano’s and Lou Malanati’s are two strong top contenders with a friendly rivalry), in the mood for some steak, or looking to sample our delicious vegan cuisines, you’ll find amazing options around every corner.
Day 1: Get Your Art On!
Start your weekend in Chicago off with our area’s most famous art installations and exhibits. Start your day in the beautiful Millenium Park, where you can admire the world’s favorite legume: The Bean! Pictures don’t do justice to how wonderfully wonky this contemporary sculpture is. Afterwards, take a quick walk over to the Art Institute of Chicago, where you’ll find famous pieces like American Gothic, The Old Guitarist, and, of course, A Sunday on La Grande Jatte, featured in the cult-classic Ferris Bueller’s Day Off.
In the mood for more museums? Chicago has so many to choose from! Do your feet a favor though and just choose one or two to visit – Chicago will be ready to welcome you back when you come visit again! Hop on the bus or train and check out the:
Finish off your day with some beautiful live music, at either the Kingston Mines or Green Mill – both famous for their live jazz and blues nights.
Day 2: Take it Slow
After a busy day yesterday, you’re probably ready to relax a little today. Continue your Chicago weekend trip and board a water taxi to take a stroll down at Navy Pier. Here you’ll find family-friendly eateries, beer gardens, and the Chicago Shakespeare Theater. Afterwards, hop on the bus or take a quick 10 minute drive over to the free Lincoln Park Zoo, home to nearly 200 species of wildlife and located just a quick walk from North Avenue Beach. Tour the zoo, then head to the sand at Lake Michigan’s shore to rest your feet (or play a round of volleyball!).
End your day just a little further north in Wrigleyville with a Cubs game (or go watch the White Sox at Guaranteed Rate Field – we won’t tell!).
Day 3: We’ve Saved the Best for Last!
Start your final day in the Windy City at the Magnificent Mile, known for its luxury shopping and amazing restaurant scene. Stop by the Starbucks reserve for the most unique cup o’ joe you’ve ever had. In addition to the classic drinks you know and love, the 4-floor experience (with an additional rooftop terrace!) has experimental and cocktail bars featuring unique experiences like nitrogen-infused gelato, cold brew spiced rum, and a whiskey barrel-aged malt milkshake.
Now that you’re wide awake and alert, board Chicago’s First Lady at the corner of Michigan Avenue and Wacker Drive for a riverboat cruise throughout the city’s waterways. Voted the #1 Board Tour in the U.S. by USA TODAY, this is the only boat tour led by professional docents from the Chicago Architecture Center. Enjoy 360° unobstructed views of the city’s skyline with an open-air upper deck and covered lower deck with wall-to-wall windows. See for yourself why Chicago's First Lady was rated TripAdvisor’s #1 boat tour of the city!
For some final laughs, finish your day off at The Second City, one of Chicago’s most popular comedy theaters and the origin of famous comics like Tina Fey, Steve Carrell, and both Keegan-Michael Key and Jordan Peele. The world-famous sketch and improv club is located in Chicago’s historic Old Town, the perfect place for a bite to eat before closing out the night.
Where Will the Windy City Take You?
Whether it’s relaxing on the beach, taking in the sights on a riverboat cruise, or cheering on one of our many sports teams, there’s something for everyone in our fabulous city. We hope you have an amazing trip – and that we get to see you again soon!
See the best views the Windy City has to offer aboard Chicago’s First Lady! See Chicago in a whole new light and learn the amazing history behind famous sights throughout the city. Reserve your ticket, grab a seat, and get ready to set sail!
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