How To Spend A Weekend In Chicago

Chicago has something for everyone, but it can feel overwhelming. You could spend weeks exploring just the downtown area without even thinking about the surrounding neighborhoods. So it can be difficult to determine what to squeeze into your trip. If you’re just in town for a weekend, use this guide to help you make the most of the Windy City.

Friday Night

Start off your weekend downtown with dinner and a show. Try Hot Woks Cool Sushi for budget-friendly Asian cuisine, The Berghoff for authentic German, or McCormick & Schmick’s for upscale seafood and steak. And even if you can’t get seats at Hamilton, Broadway in Chicago always has a world-class array of performances in the Loop. Musicals, comedy, traveling shows, and originals make up their impressive repertoire.

For a nightcap, pop into one of Chicago’s best winter bars in the downtown area. Also, consider Potter’s Lounge for a classy vibe or Miller’s Pub for a more laid-back one.

Saturday is your biggest day to sightsee, so hop out of bed early and grab breakfast at the Bongo Room in the South Loop or one of Chicago’s five Yolk locations. Make it your daytime mission to see the city highlights, like a visit to the Willis Tower, the Bean, and a stroll up Michigan Avenue. Hit a museum (or several) and squeeze in tours of Chicago’s best architecture and most impressive public works of art along the way.

In between everything, try grabbing lunch somewhere with a bit of culture. Get a taste of Chicago’s ethnic food scene in Greektown, Chinatown, or Little Italy.

Saturday Night

It’s time to dust off your dancing shoes and dip your feet into Chicago’s nightlife scene. Consider snagging tickets to a killer concert, or just get ready to hit the bars. For all-night beats and plenty of fun, check out the State and Division area or head north to Wrigleyville. The Original Mother’s, McFadden’s, Sluggers, and Trader Todd’s are all crowd-pleasing favorites. For something more low-key, find yourself a welcoming dive bar, or belt your heart out at karaoke.

Sunday Morning

Saturday was a marathon, so keep things more relaxed on Sunday. Get out of the city center and pick an outer neighborhood to explore. Wicker Park is one of the most popular off-Loop destinations for awesome cafés, boutique shopping, and general quirkiness. Check out Mojo Spa, The Wormhole Coffee and the 606. Lincoln Park has a free zoo, lake views, and all the food options you can handle. Stop at Oz Park, Sweet Mandy B’s, and Art Effect. And the Near West Side has a bit of everything, including intimate music venues, mind-blowing Italian food, and a thriving art scene. Hit the Bottom Lounge, Pompei, and the historic Maxwell Street Market.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

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