The nation’s third-largest city covers a lot of ground, but you can take in a good chunk of Chicago during a weekend if you have a plan. And we’ve got one with sky-high buildings and star art collections, along with dive bars and Route 66 diners.
Here’s our guide to the perfect weekend itinerary in Chicago.
Friday
Afternoon
Head to the docks beneath Michigan Avenue downtown and hop on a boat tour with the Chicago Architecture Center. While it’s touristy, the experience is marvelous. Grab a seat on deck and look up as you glide past the finest collection of buildings in the country. Guides’ architecture lessons will enhance your experience, so by the journey’s end, you’ll know your Beaux Arts from International Style.
After expanding your architectural knowledge, it’s time to indulge in deep-dish pizza, Chicago’s quintessential local specialty. Giordano’s makes a “stuffed” pie that’s a bigger, doughier version – think deep-dish on steroids. Get ready, because each cheese-laden slice weighs about a half-pound.
Evening
Next, head north a few miles to catch a show at Second City, the launching pad for comedic talents like Bill Murray and Tina Fey. The outrageous sketch revues ensure a high-quality laughter experience. As it is very popular, be sure to secure tickets in advance.
Before calling it a night, enjoy a drink at the Old Town Ale House, located across the street from Second City. This vibrant space attracts a diverse crowd, providing a unique and authentic atmosphere, where locals and visitors mingle beneath eye-catching artwork until the early hours.
Saturday
Morning
Start your day at downtown’s western edge with a visit to Lou Mitchell’s, a classic diner that has stood the test of time since the Route 66 era. The charming waitstaff will serve up fluffy omelets and impressive pancakes, while free donut holes keep you energized while you wait for your table.
After breakfast, walk a few blocks to Willis Tower, Chicago’s tallest building reaching 1,450 feet into the sky. The Skydeck on the 103rd floor offers a breathtaking panorama over four states. For the adventurous, brave souls can step onto the glass-floored Ledges for a thrilling experience of being suspended in mid-air. Make sure to purchase tickets ahead of time.
Afternoon
Stay downtown and make your way to the Art Institute of Chicago. The second-largest art museum in the country displays an impressive collection of masterpieces, especially from the Impressionist and Post-Impressionist eras.
Don’t miss Georges Seurat’s pointillist masterpiece A Sunday Afternoon on the Island of La Grande Jatte or Grant Wood’s iconic American Gothic. You’ll also be captivated by Marc Chagall’s stunning America Windows.
Once you’ve soaked in the art, head to the Art Institute’s 3rd-floor sculpture terrace and cross the pedestrian bridge into Millennium Park. Snap a photo at the famous “Bean” sculpture and cool off at Crown Fountain, where locals’ video images spout water. Take a moment to appreciate Frank Gehry’s fabulous band shell before treating yourself to a Nutella soufflé pancake and ginger tea at Hanabusa Cafe.
Evening
Take the Blue Line L train to Logan Square, a lively neighborhood just 20 minutes northwest of downtown. This area is a foodie paradise. Pop into Revolution Brewing for a Rosa hibiscus ale or other locally brewed creations.
Make your way a mile southwest to Giant, a small venue renowned for its modern American comfort food flavors. Reservations are a must, but if you can’t grab a spot, Ground Control offers fantastic vegetarian options, including tofu fried chicken and beer-braised greens paired with local brews and budget-friendly cocktails.
After dinner, stroll over to Rosa’s Lounge. This iconic blues venue offers an authentic experience with live performances echoing Chicago’s rich musical history. It’s wise to buy tickets in advance, though you may be able to walk up after the first set starts around 11pm.
Sunday
Morning
Chicagoans relish brunch, and the West Loop boasts an array of trendy spots to satisfy your cravings. The Publican presents honey butter waffles, pork belly hash, and hefty Bloody Marys, while Top Chef winner Stephanie Izard’s Little Goat impresses with cheesy hash browns and spiced apple pancakes. Roister takes chicken and waffles and biscuits and gravy to new heights with its innovative dishes.
Afternoon
If it’s baseball season and the Cubs are playing, hop on the Red Line train to Wrigley Field. This charming ballpark, built in 1914, is known for its ivy-covered outfield walls and hand-turned scoreboard. Enjoy hot dogs and beer while taking in the electric atmosphere from the bleacher seats.
Alternatively, explore the Pilsen neighborhood, a vibrant mix of Chicago’s Mexican culture and artistic flair. Spectacular murals color its streets, enhancing its lively community feel.
Embark on a walkabout with Pilsen Public Art Tours to delve deeper into the area. If hunger strikes, savor delicious pork tacos at Don Pedro Carnitas or indulge in rich, complex mole dishes at 5 Rabanitos. Take the Pink Line L train to 18th Street to reach this artistic haven.
Where to Stay
Downtown (aka the Loop): Explore cool boutique and architectural properties in the heart of the city, just steps away from Millennium Park and the Art Institute. The distinctive Virgin Hotel features spacious, uniquely designed rooms in a former art deco bank tower, while the Silversmith offers gem-inspired vintage rooms in a historic jeweler’s building.
West Loop: This area is bursting with trendy accommodations surrounded by fashionable bars and restaurants. The Publishing House Bed & Breakfast offers a unique experience with stylish rooms named after notable Chicago writers. Meanwhile, the Hoxton Chicago features mid-century-modern decor, complimentary bicycles, and a lively rooftop cafe.
How to Get to Chicago
O’Hare International Airport is located on the city’s northwest side and is the primary arrival point for international flights. Midway International Airport, situated on the south side, is smaller but also provides convenient connections to downtown. Both airports feature easy access via the L train, with costs of $5 and a 40-minute ride from O’Hare, versus $3 and 30 minutes from Midway. Additionally, Amtrak services arrive at Union Station in downtown Chicago.
This article was first published on September 9, 2019, and was last updated on May 9, 2022.
