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. Moreover, this guide includes sky-high buildings, exceptional art collections, dive bars, and iconic Route 66 diners.
Friday
Afternoon
Head to the docks beneath Michigan Avenue downtown and hop on a boat tour with the Chicago Architecture Center. Yes, it’s touristy, but it’s also marvelous. Grab a seat on deck and look up as the finest collection of buildings in the country glides by. Guides’ architecture lessons carry on the breeze, ensuring you’ll know your Beaux Arts from International Style by the journey’s end.
After soaking in knowledge, it’s time to savor some deep-dish pizza, Chicago’s premier local specialty. Giordano’s makes a “stuffed” pie, which is a bigger, doughier version – like deep-dish on steroids. Consequently, each cheese-laden slice weighs about a half-pound.
Evening
Next, motor north a few miles to catch a show at Second City, the launching pad of comedic talent from Bill Murray to Tina Fey. The outlandish sketch revues are always high-quality laugh fests. They’re also popular, thus, plan on arriving early.
Before the night wraps up, grab a drink at the Old Town Ale House, across the avenue from Second City. It’s a wonderfully democratic establishment, where individuals from various backgrounds gather under the nude celebrity paintings until 4 a.m. You might even see cast members from your show enjoying a late-night brew.
Saturday
Morning
Start at downtown’s western edge and fuel up at Lou Mitchell’s, a diner that harks back to when Route 66 rolled by. The old-school waitresses genuinely enhance your experience with friendly service while delivering fluffy omelets and plate-defying flapjacks. Lines can be long, but Lou’s offers free donut holes and Milk Duds to sweeten the wait.
Walk a few blocks east to Willis Tower. Chicago’s tallest building pokes 1,450ft into the heavens, and its 103rd-floor Skydeck provides a stunning panorama over four states. Brave souls can step onto the glass-floored Ledges to experience an exhilarating sensation of being suspended in mid-air.
Afternoon
Stay downtown and mosey to the Art Institute of Chicago (advance reservations might be necessary). The second-largest art museum in the country offers an abundance of masterpieces, particularly impressionist and post-impressionist works.
Don’t miss Georges Seurat’s pointillist A Sunday Afternoon on the Island of La Grande Jatte; Grant Wood’s iconic American Gothic is also a must-see. Marc Chagall’s radiant stained glass America Windows fills a room, creating a captivating atmosphere.
When you’ve seen your fill of art, head to the Art Institute’s 3rd-floor sculpture terrace and step onto the silvery pedestrian bridge arching into Millennium Park. Make a beeline for the shiny “Bean” sculpture for an obligatory photo op, then splash around in Crown Fountain, where video images of locals spout gargoyle-style. Marvel at Frank Gehry’s swooping silver band shell. Consequently, unwind with a Nutella soufflé pancake and ginger tea at Hanabusa Cafe.
Evening
Take the Blue Line L train to Logan Square, a vibrant neighborhood 20 minutes northwest of downtown, perfect for food enthusiasts and nightlife seekers. Make a stop at Revolution Brewing for a Rosa hibiscus ale or other inventive beers while mingling with the local crowd.
Progress a mile southwest to Giant, a small storefront known for crafting bold flavors in modern American comfort food. Make sure to plan ahead as reservations are essential. If you can’t secure a seat, nearby Ground Control garners praise for its tofu fried chicken, beer-braised greens, and other vegetarian dishes served alongside local brews and budget-friendly cocktails.
From here, it’s a quick hop to Rosa’s Lounge. Authentic electric blues thrived in Chicago when Muddy Waters, Howlin’ Wolf, and their peers plugged in their amps, and Rosa’s remains a genuine spot to enjoy a remarkable performance. It’s advisable to purchase tickets ahead of time, although usually, one can walk up and get in after the first set (around 11 p.m.).
Sunday
Morning
Chicagoans take their brunch seriously, and the West Loop hosts numerous stylish hot spots for a delicious meal. The Publican serves honey butter waffles, pork belly hash, and hefty Bloody Marys, while Top Chef winner Stephanie Izard’s Little Goat showcases cheesy hash browns and spiced apple pancakes. For a more traditional touch, Roister serves chicken and waffles and biscuits and gravy that surpass expectations.
Afternoon
If it’s baseball season and the Cubs are at home, jump on the Red Line train to Wrigley Field. The 1914 ballpark captivates with nostalgic elements like ivy-covered outfield walls and a hand-turned scoreboard. Enjoying hot dogs and sipping beer in the lively bleacher seats creates an exceptional afternoon experience.
Otherwise, head to the Pilsen neighborhood, where the vibrancy of Chicago’s Mexican community meets the hipster underground. Wild murals adorn nearly every building, providing a colorful backdrop for exploration.
A walk with Pilsen Public Art Tours makes for a great way to experience the area. Feeling hungry? Delight in sublime pork tacos at Don Pedro Carnitas or savor the complex, mole-rich dishes at 5 Rabanitos. The Pink Line L train to 18th Street offers easy access to this vibrant neighborhood.
Where to stay
Downtown (aka the Loop): Cool boutique and architectural properties fill the core location, offering easy access to Millennium Park, the Art Institute, and other top attractions. The playful Virgin Hotel provides sizable, cleverly conceived rooms in an old art deco bank tower, while the Silversmith reflects a gem-inspired, vintage-cool aesthetic within a Gilded Age jewelers building.
West Loop: Chicago’s trendiest accommodations pop up in the West Loop, surrounded by a myriad of fashionable bars and restaurants. The Publishing House Bed & Breakfast positions you right in the heart of it, with stylish rooms named after Chicago writers. The Hoxton Chicago combines mid-century-modern-inspired decor with free bicycles and a lively rooftop cafe.
How to get to Chicago
O’Hare International Airport, located on the city’s northwest side, is larger and where most international flights arrive. Smaller Midway International Airport is situated on the south side, offering easy access to downtown via the L train, priced at $5 and taking 40 minutes from O’Hare and $3 and 30 minutes from Midway. Furthermore, Amtrak arrives downtown at Union Station.
This article was first published on September 9, 2019, and updated on May 9, 2022.
