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. 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, so you’ll know your Beaux Arts from International Style by journey’s end.
After stuffing your head with knowledge, it’s time to stuff your face with deep-dish pizza, Chicago’s premier local specialty. Giordano’s makes “stuffed” pie, which is a bigger, doughier version – like deep-dish on steroids. Loosen the belt, because each cheese-laden slice weighs a half-pound or so.
Evening
Next, motor north a few miles to catch a show at Second City, the launching pad of jokesters from Bill Murray to Tina Fey. The outlandish sketch revues are always high-quality laugh fests. They’re also popular, so book tickets well in advance.
Before the night ends, get a drink at the Old Town Ale House, across the avenue from Second City. It’s a wonderfully democratic institution (some might call it a dive bar), where beautiful people and seen-it-all regulars mingle on barstools under the nude celebrity paintings until last call at 4am. You might even see cast members from your show hanging out over a wee-hour brew.
Saturday
Morning
Start at downtown’s western edge and fuel up at Lou Mitchell’s, a diner from the days when Route 66 rolled by the area. The old-school waitresses call you “doll” while delivering fluffy omelets and plate-defying flapjacks to the table. Lines can be long, but Lou’s soothes the pain with free donut holes and Milk Duds as you wait for your table.
Walk a few blocks east to Willis Tower. Chicago’s tallest building pokes 1450ft into the heavens and its 103rd-floor Skydeck provides a panorama over four states. Brave souls can step onto the glass-floored Ledges to be suspended (almost) in stomach-lurching mid-air. Be sure to book tickets beforehand.
Afternoon
Stay downtown and mosey to the Art Institute of Chicago (advance reservations required). The second-largest art museum in the country hangs masterpieces aplenty, especially impressionist and post-impressionist pieces.
Georges Seurat’s pointillist A Sunday Afternoon on the Island of La Grande Jatte is here; so is Grant Wood’s American Gothic. Marc Chagall’s glowing stained glass America Windows fill a room, too.
When you’ve seen your fill, 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 the obligatory photo op. Splash around in Crown Fountain, where video images of locals spout gargoyle-style. Admire Frank Gehry’s swooping silver band shell. Then contemplate it all over a Nutella soufflé pancake and ginger tea at Hanabusa Cafe.
Evening
Take the Blue Line L train to Logan Square, a buzzy neighborhood 20 minutes northwest of downtown – prime for chowhounds and tipplers. Drop in at Revolution Brewing to knock back a Rosa hibiscus ale or other inventive beer with the local crowd.
Make your way a mile southwest to Giant, a small storefront cooking up big flavors in modern American comfort food. Advance reservations are essential. If you can’t score a seat, no worries: nearby Ground Control earns praise for its tofu fried chicken, beer-braised greens and other vegetarian dishes served with a side of local brews and budget cocktails.
From here it’s a stone’s throw to Rosa’s Lounge. The electric blues became Chicago’s tune when Muddy Waters, Howlin’ Wolf and friends plugged in their amps in the 1950s, and Rosa’s is an authentic spot to hear a fret-bending set.
The humble venue brings real-deal players to its arm’s-length-away stage where guitars wail into the night. It’s wise to buy tickets in advance, though you usually can walk up and get in after the first set (around 11pm).
Sunday
Morning
Chicagoans go gaga for brunch, and the West Loop provides loads of stylish hot spots to get your eggs on. The Publican delivers honey butter waffles, pork belly hash and hefty Bloody Marys, while Top Chef winner Stephanie Izard’s Little Goat shows how it’s done with cheesy hash browns and spiced apple pancakes. Roister makes chicken and waffles and biscuits and gravy that go way beyond the traditional versions.
Afternoon
If it’s baseball season and the Cubs are playing, hop on the Red Line train to Wrigley Field. The 1914 ballpark charms with retro touches like ivy-covered outfield walls and a hand-turned scoreboard. Shoveling down hot dogs and drinking beer in the raucous bleacher seats makes for an exceptional afternoon.
Otherwise, aim for the Pilsen neighborhood, a mash-up of Chicago’s Mexican community and hipster underground. Wild murals radiate off the buildings on practically every street.
A walkabout with Pilsen Public Art Tours is a good way to explore. Hungry? Bite into sublime pork tacos at Don Pedro Carnitas or complex, mole-rich dishes at 5 Rabanitos. The Pink Line L train to 18th Street gets you there.
Where to stay
Downtown (aka the Loop): Cool boutique and architectural properties fill the core, where you’re steps away from Millennium Park, the Art Institute and other top sights. The playful Virgin Hotel offers large, cleverly conceived rooms in an old art deco bank tower, while the Silversmith flashes gem-inspired, vintage-cool rooms in a Gilded Age jewelers building.
West Loop: Chicago’s most trendsetting accommodations pop up in the West Loop, surrounded by heaps of fashionable bars and restaurants. The Publishing House Bed & Breakfast puts you in the thick of it, with 11 stylish rooms named after Chicago writers. The Hoxton Chicago brings mid-century-modern-inspired decor to its creative digs, along with free bicycles and a festive rooftop cafe.
How to get to Chicago
O’Hare International Airport is on the city’s northwest side; it’s larger and where most international flights arrive. Smaller Midway International Airport is on the south side. Both have easy links to downtown via the L train, which costs $5 and takes 40 minutes from O’Hare, and $3 and 30 minutes from Midway. Amtrak arrives downtown at Union Station.
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