Looking for a fun weekend getaway from New York City (or anywhere in the states for that matter)? A long weekend in Chicago may be just what the doctor ordered! Visitors to Chicago can expect to find a vibrant city bustling with activity any time of year.
On any given summer weekend, locals and tourists alike will be out in full force, making the most of the sunshine and glorious weather. There will be farmers’ markets on any given day, festivals, and crowds galore, but that only adds to the merriment.
Join in the fun by heading to any of these fabulous spots where Chicago hospitality and beauty really shine.
A Long Weekend in Chicago
What to See and Do on Your Long Weekend in Chicago
Lake front and Seeing the Sights
Nothing will bring a quicker appreciation for the sheer size of Lake Michigan than standing on its shore and looking out at the endless body of water. The easiest way to do this is to walk east and you will find yourself along the water, but if you want an in-depth overview of the city and its sights, consider taking a tour.
Bobby’s Bike Hike is a great way to explore the city on two wheels. You can find fun tours such as “Bikes, Bites, and Brews” or “Southside Gangster Bike Tour”, whichever one you choose you are sure to experience a great overview of the city.
If bikes aren’t your thing, consider a tour on the water. Several companies offer fantastic architecture tours along the Chicago River or rent a kayak and head out to explore the river on your own.
Voted the #1 museum in the world, The Art Institute of Chicago has more than 300,000 works of art, spanning the centuries. From Ancient Greece and China to the Renaissance and Impressionism, the museum covers it all. The modern collection is outstanding in its own right.
Most visitors seek out Van Gogh’s The Bedroom and A Sunday Afternoon on the Island of La Grande Jatte by Seurat, but don’t single out those paintings and miss the other museum masterpieces. The museum is meant to be enjoyed, so plan on spending a few hours perusing the galleries.
Any long weekend in Chicago needs to include this green space! Millennium Park is the place to be in Chicago any time of year. The park is home to the infamous Cloud Gate (The Bean), Pritzker Pavilion, and Crown Fountains, and many tourists head straight for these three to capture iconic Chicago photographs.
However, the park offers more than selfie opportunities; it’s the heart of the city and it offers concerts, films, festivals, and more. If you love people watching and want to see what Chicago is all about, head to the park and blend in with the crowd.
Go up in the Sky
There are many places to find a view of the city if you’re not afraid of heights! Willis Tower and its Skydeck Ledge (a glass box, 1353 feet in the air, extends out four feet from the side of the building) offer views spanning four states on a clear day.
360 Chicago on the 94th floor of the John Hancock building has concerts and sunset views as well as TILT, which will have you leaning out at a 30 degree angle from the side of the building. It’s definitely not for the faint of heart, yet a thrill for those looking for something somewhat crazy to do during their long weekend in Chicago.
If you’re not a daredevil and want a place with a great view for cocktails or dinner, try one of the city’s rooftop bars. Favorites include The Peninsula, Loews, and Wit hotels, as well as Cindy’s above the Chicago Athletic Association and Green River.
Where to Eat on Your Long Weekend in Chicago
You can’t go wrong in Eataly with its multiple restaurants, cafés, and carry away counters. Everything is Italy centric from pizza and pasta to seafood and vegetable dishes. Don’t miss the Nutella bar for breakfast (!!!) and the gelato bar for a sweet afternoon treat. Whatever Italian food your heart desires, you’re sure to find it at Eataly.
The Purple Pig is located in the heart of downtown, just off Michigan Avenue. It focuses on cheese, swine and wine, and serves most dishes as small plates in a large dining room with some community tables. A unique dining experience in the city, definitely not to be missed.
Frontera Grill (or any Rick Bayless restaurant)
Rick Bayless is synonymous with delicious Mexican cuisine in Chicago. If you can’t grab a reservation at Frontera Grill, head to Topolobampo or Xoco. All of the restaurants offer something different, but they’re all good. Just go, you can thank me later.
Don’t Skip the Doughnuts
For some reason, Chicago is going through a doughnut craze, and to miss out on the fun would almost ruin your weekend. So if you see any of the following places, be sure to duck in and try one of their specialties. Doughnut Vault, Glazed & Infused, and Do-Rite Donuts will all satisfy your sweet tooth.
A long weekend in Chicago can be as busy or relaxed as you want to make it. Head for the water or dig into the city scene, whatever vibe you’re looking for, Chicago has it in spades.
Kirsten is the founder of Kids Are A Trip, and the Chicago Mombassador for Momaboard. A bilingual teacher, she believes travel is an education and feels fortunate she can teach her children about different cultures as the family has traveled to 25 countries and counting. A native Phoenician, Kirsten currently lives in Chicago with her husband and three boys.