Chicago – How to Have a Perfect Weekend

The third largest city in the country covers a lot of land, but if you have a plan you can take in a good chunk of Chicago on the weekend. And we also have dive bars and Route 66 diners with art collections of skyscrapers and stars.

Here’s our guide to the perfect weekend getaway in Chicago.

Friday

afternoon

Head down downtown Michigan Avenue to the docks and take a boat tour with the Chicago Architecture Center. Yes, it’s touristy, but it’s also spectacular. Grab a seat on the deck and take in the best collection of buildings in the country. The guides’ architecture lessons are a breeze, so you’ll know your Beaux Arts international style by the end of the trip.

After filling your head with knowledge, it’s time to stuff your face with deep dish pizza, Chicago’s biggest local specialty. Giordano’s makes “Stuffed” pie, which is a bigger, doughier version — like deep dish on steroids. Loosen the belt, because each cheese-filled slice weighs half a pound or more.

the evening

Then, motor a few miles north to catch a show at Second City, the launching pad for jokesters from Bill Murray to Tina Fey. Foreign sketch revues are always high quality comedy shows. They are also popular, so book tickets in advance.

Before the night ends, grab a drink at Old Town Alehouse across the avenue from Second City. It’s a wonderfully democratic establishment (some might even call it a dive bar), where beautiful people and all the regular nudists can be seen mingling on bar stools under celebrity paintings until last call at 4am. . You can even see your show’s cast members rotate in one hour intervals.

Saturday

Morning

Start on the west side of town and refuel at Lou Mitchell’s, a diner from the days when Route 66 ran through the area. Old-school waitresses call you “doll” while delivering fluffy omelets and plate-defying flapjacks to the table. Lines can be long, but Lowes eases the pain with free donut holes and milk duds while you wait for your table.

Walk a few blocks east of Willis Tower. Chicago’s tallest building soars 1,450 feet into the sky, and its 103rd-floor sky deck offers a panorama over four states. Brave souls can step onto glass-floored ledges that can be suspended (almost) in mid-air in the stomach. Make sure to book tickets in advance.

afternoon

Stay downtown and the Art Institute of Chicago (advance reservations required). The country’s second largest art museum hangs masterpieces, especially Impressionist and Post-Impressionist pieces.

George Sievert’s point list Sunday afternoon on the island of La Grande Jatte here is; So is Grantwood’s. American Gothic. Sparkling Stained Glass by Marc Chagall America Windows Fill a room too.

When you’ve had your fill, head to the Art Institute’s third-floor sculpture terrace, and step onto the silver pedestrian bridge that arches over Millennium Park. Make a beeline for the glittering “Ben” statue for the obligatory photo op. Splash around the Crown Fountain, where video images of locals are reflected gargoyle-style. Admire Frank Gehry’s Silver Band shell. Then consider topping it with a Nutella soufflé pancake and ginger tea. Hanabusa Cafe.

the evening

Take the Blue Line L train to Logan Square, a bustling neighborhood 20 minutes northwest of the city — prime for chowhounds and tipplers. Come to Revolution Brewing to knock back Rosa hibiscus ale or other innovative beers with the local crowd.

Make your way a mile southwest to Giant, a small storefront that dishes out big flavors in modern American comfort food. Advance reservation is essential. If you can’t score a seat, don’t worry: nearby Ground Control praises its tofu fried chicken, beer-braised greens and other vegetarian dishes served with local wines and budget cocktails.

From here, Rosa’s Lounge is a stone’s throw away. Electric blues became a Chicago tune in the 1950s when Muddy Waters, Howlin’ Wolf and friends plugged in their amps, and Rosa’s is an authentic place to hear a snarl-bending set.

The humble venue brings real-deal players an arm’s length away from the stage where the guitars howl into the night. It’s wise to buy tickets in advance, although you can usually walk in after the first set (around 11pm).

Sunday

Morning

Chicagoans go gaga for brunch, and the West Loop offers plenty of stylish hotspots to get your eggs on. The Publican serves up honey butter waffles, pulled pork hash and heavy Bloody Marys, while Top Boss Winner Stephanie Izard’s Little Goat shows how it’s done with cheesy hash browns and spiced apple pancakes. The roaster makes chicken and waffles and biscuits and gravy that go beyond the traditional version.

afternoon

If it’s baseball season and the Cubs are playing, hop on the Red Line train to Wrigley Field. The 1914 ballpark features charming retro touches like ivy-covered outfield walls and a hand-turned scoreboard. Guzzling down hot dogs and drinking beer on the rowdy bleacher seats makes for an extraordinary afternoon.

Otherwise, aim for the Pilsen neighborhood, a mash-up of Chicago’s Mexican community and the hipster underground. Wilderness walls spring from buildings on practically every street.

Walkabout with Pilsen Public Art Tour It’s a good way to explore. I am feeling hungry. Bite into the sumptuous pork tacos at Don Pedro Carnitas or the complex, sesame-rich dishes at 5 Rabanitos. The Pink Line L train takes you there to 18th Street.

where to stay

Downtown (aka The Loop): Cool boutiques and architectural features fill the core, where you’re steps away from Millennium Park, the Art Institute and other major attractions. The playful Virgin Hotel offers large, cleverly conceived rooms in an old Art Deco bank tower, while Silversmith glams up gem-inspired, vintage-cool rooms in the Gilded Age jewelers’ building.

West Loop: Chicago’s most trendsetting residences can be found in the West Loop, surrounded by a plethora of fashionable bars and restaurants. Publishing house Bed & Breakfast puts you in its belle, with 11 stylish rooms named after Chicago authors. gave Hoxton Chicago With mid-century modern-inspired decor in its creative digs, as well as free bicycles and a festive rooftop cafe.

How to reach Chicago

O’Hare International Airport is on the northwest side of the city; It is large and where most international flights arrive. The smaller Midway International Airport is to the south. Both have easy connections 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.