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How to Spend a Weekend in Chicago

Estimated reading time: 3 minutes

Only have a few days? This guide will give you all that you need for a perfect stay in Chicago

Spending a weekend in Chicago will go by faster than you think. You’ll discover plenty of art, music, beaches, food, and bars to keep you going until the wee hours of the morning. Here’s what you’ll want to do while you’re there.

Chicago waterfront navy pier

Chicago Waterfront

Friday Evening

When spending 72 hours in Chicago, you want to luxuriate in every second. Chicago is home to a plethora of boutique hotels, with each offering its own distinct experience. The Chicago Athletic Association boasts postcard views of Lake Michigan and Millennium Park, as well as the elegant rooms you’d expect from an 1890s building.

Other boutique hotels that might be calling your name include Soho House, with its London-inspired decor and door-to-door bar cart, or Freehand Chicago, with its stylish and comfy apartment vibe.

Your first night calls for authentic deep-dish pizza at Pequod’s Pizza. The way they caramelize cheese around the crust will make you want to eat your pizza from the outside in.

Afterward, you can work off those calories with a stroll on the Riverwalk or take a night river cruise to explore the intriguing architecture of Chicago.

Saturday Morning

You’ll want to get up early on Saturday morning to make the most of your remaining 48 hours in Chicago. At MAD Social, you’ll salivate over light, fluffy pancakes served with to-die-for salted caramel butter. For the savory seeker, chicken and churro waffles with pork belly is the ideal meal to kick off your day.

If a big breakfast isn’t your style, coffee houses like Osmium Coffee Bar will provide a hit of caffeine and a pastry to go.

You can’t stay in Chicago without taking a selfie under “The Bean” at Millennium Park. After you’ve snapped the perfect shot, you can head to the outdoor Boeing art galleries, where you’ll come across contemporary sculptural installments. Carry on with your art exploration at the Art Institute of Chicago; the architecture of the building alone is worth the trip.

millenium park chicago

Millennium Park, Chicago

You’re bound to be hungry by now, and Al’s Italian Beef has an authentic Italian beef sandwich that’ll hit the spot. They’ve been serving their tantalizing marinated beef and messy gravy on a bun since 1938.

Saturday Evening

Saturday night in Chicago calls for cocktails at Salone Nico in the Thompson, a Chicago boutique hotel. Then, you’ll want to catch the sunset from above at The Skydeck Chicago, or head to the John Hancock Observatory for unparalleled views of the city at night.

The sun has set, and you’re ready for fun. You’ll hear an eclectic mix of performers at The Hideout, soul-searching blues at Blue Chicago, and smooth jazz at the Green Mill.

art institute of chicago

Art Institute of Chicago, Chicago

For dinner, you can indulge in a high-end meal in a casual space at Giant, experience the farm-to-plate innovations at Lula Cafe, or treat your taste buds at the three-Michelin-star restaurant, Alinea.

You can take a self-guided tour of the city’s historic speakeasies, where thirsty locals shared clandestine cocktails during prohibition. You might even test your luck at an authentic 1920s speakeasy, such as The Drifter. It’s in the basement of the Green Door Tavern, and you still have to knock on the door and wait to get in.

Sunday Morning

With just 24 hours in Chicago left, you’ll be up early on Sunday morning. Head to Mindy’s Hot Chocolate for a plate of mouthwatering steak and eggs or French toast to fuel your day.

You can stretch your legs and take a walk along the 606, an elevated park that was built on one of the city’s abandoned railway lines. It has perfect stop-offs for lunch like the beer garden at Handlebar for their “I can’t believe it’s vegan menu,” or you can try the low-key martinis-at-noon vibe at Weegee’s Lounge.

Chicago’s beaches invite lazy sun basking, curious people watching, and outdoor activities for the more adventurous tourist. The Lurie Garden is a quiet haven in the heart of the city with stunning landscaping and private benches to lounge on.

If you’d rather a more hair-raising start to your day, you’ll find it on a Chicago Crime Tour. You can explore the city’s ties to the mob for a fascinating look at Chicago’s notorious past.

Sunday Evening

Why not spend your last hours in Chicago laughing? Giggle and gasp at one of Chicago’s iconic comedy clubs, such as Second City, iO, or Annoyance Theatre. For a one-of-a-kind entertainment experience, The Blue Man Group puts on electrifying performances that mix humor, technology, and music at the Briar Street Theatre.

theater district chicago

Theater District, Chicago

Experience the diverse melting pot of Chicago’s neighborhoods with dinner in Greektown on the West Side. Rodity’s has been around for over 35 years, offering an old-school dining experience with homecooked authentic Greek grilled octopus, saganaki, moussaka, dolmades, and more.

For the full Chicago foodie experience, a Chicago hot dog is a must. Wiener Circle is not only known for its dogs, but also its mouthy servers who will tease with well-intentioned banter while serving up their famous fully topped char dog. And that’s a wrap on your Sunday night in Chicago!

Your Chicago weekend offers everything you need to kick back and relax, from art and music to food and drink. Book your getaway today.

Check out our other Weekend Guides for our top destinations

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Las Vegas

Nashville

New Orleans

Atlanta

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