three-day long weekend itinerary for Chicago
This post may contain affiliate links. For more information, please see the terms page.
Chicago is the greatest place in the world, and I’m not the only person who thinks so!
There’s something to do 24 hours a day here, which makes it the perfect city for a three-day weekend vacation. You’ll get a lot of bang for your buck with its easy accessibility (two airports, an Amtrak and Greyhound station, and plenty of city-wide public transportation to get you where you want to go), things to do in any weather or season, and relatively central location.
Spending your first evening downtown is great, because you can knock out a lot of city “must do”‘s in one location. Grant Park, Chicago’s front lawn, is home to the Bean, Buckingham Fountain, and many other public artworks. Take a selfie at the cloud, grab a Divvy bike and admire Lake Michigan from the Lakefront Trail, and in the winter months, skate on the ice rink!
Rainy day? Stay dry and see the city anyway on one of the many bus tours! From crime and mobster history to architecture and Chicago lore, there’s no lack of ways to
Afterward, hop on a Divvy Bike to burn off some of that carb-y energy and head over to the Riverwalk, where you can take your pick of a post-dinner treat while walking the trail. It’s also near the Magnificent Mile so you can scratch that shopping itch at souvenir shops, Water Tower Place, or other major retailers like Apple, Louis Vuitton, and more. (Like a Nutella Cafe. You’re welcome.)
On Saturday morning, grab a coffee from Fairgrounds or Goddess and the Baker and stop by the free Chicago Cultural Center. With rotating exhibits and stunning architecture, it’s a popular spot for new visitors and locals alike.
Then, head over to Old Town and grab a table at The Whale or Farmhouse, depending on your party’s tastes. Stick around the neighborhood to hit another one of the city’s most “can’t miss” institutions, the Lincoln Park Zoo! They’re open 365 days a year and is always free of charge. (Concessions are surprisingly affordable, too.) Visit Alexander Camelton, check out some presentations by zookeepers and volunteers (I especially love learning about the polar bears and sea lions) and walk around another one of the city’s amazing parks. If your zoo day is rained out, the Chicago History Museum sits at the south end of the park.
Hop on the Blue Line to the Damen stop to spend the rest of the afternoon in trendy Wicker Park and Bucktown. Grab a tasty treat from Stan’s Donuts, stop in to bookstores Volumes, Myopic, and Quimby’s (all independent, all great for their own reasons,) and pop into Corbett vs. Dempsey, a free art and culture museum in the Dusty Groove building. Wicker Park is also a great spot to grab an Italian Beef, a classic meal – Jay’s Beef is easy to get to.
Rainy day? Try out an escape room – we have them all over the city. If you don’t like solving puzzles, try a more traditional arcade, like Headquarters Beercade or Emporium. My favorite is Ignite, a video game lounge in Skokie and Avondale – I could play Rock Band for hours and hours (and have on more than one occasion!)
For dinner, since you’re already in Wicker Park, make a beeline for Small Cheval. The little sister restaurant of Au Cheval, it’s more affordable and more relaxed, but still serves one of the city’s best burgers. Their shakes and fries aren’t anything to shake a stick at, either!
The Second City has been home to more successful comedians than you can count. They have several stages and several shows every night, so do yourself a favor and stop by to see the next big things.
Afterward, hop over to Humboldt Park and my favorite bar in the city for a nightcap – The California Clipper is a dimly lit former 1930’s movie theater with a speakeasy feel. Opening at 8, it can often be empty for the first few hours, which always makes me feel like I have some kind of secret gem in the city. That doesn’t last long, though – once the music starts and 10pm approaches, you’re lucky to grab a spot to stand, and the party keeps going until 3am. Grab a Pago Pago with old-fashioned shaved ice… so good.
Spend a low-key Sunday morning in the Andersonville neighborhood. Foursided, Woolly Mammoth, and Women and Children First are just a few of the funky specialty shops you’ll find here. When your feet are tired, your arm is weighed down by reusable shopping bags (Chicago has a bag tax, which will add up after a long weekend!), and your wallet is feeling light, grab one of the best brunches of your life at Big Jones.
On your way out of town, head south to Pilsen. This up-and-coming neighborhood is growing fast – in the span of a year there have been so many new businesses, restaurants, and events popping up that there’s always something new to do!
Grab dinner at the award-winning Dusek’s in the historic Thalia Hall building, or head downstairs to one of my favorite spots in the city, Punch House. With a cool 70’s vibe, boozy punch on tap, low lighting, board games and cozy booths, it’s a great spot to unwind and end your time in the city!
None of these activities sound like your speed? Don’t worry – the city of Chicago’s got your back. Request a Chicago Greeter to show you around and get a personalized offbeat experience!