Great Chicago Day
No city summers better than Chicago.
Here in Chicago, when a summer Saturday rolls around with blue skies, warm weather, and a clear calendar, there is no better way to spend the day than frolicking around the city with no particular agenda other than to take in as many of the sights, sounds, tastes and experiences as the city has to offer. Many cities may boast about a similar mix of food, architecture, cultural institutions, accessibility and diversity, but Chicago sets up remarkably well for this sort of impromptu adventure. Yes, there’s crime. Yes, there’s segregation. Yes, there’s cold, shitty weather a few months of year. But taken as a whole, the pros of this metropolis far outweigh the cons. You can enjoy a coffee here, a cocktail there, maybe take a dip in the lake, catch a few innings of a game, peruse some art, wander through a street fest, pop in on some friends, and late night dine your heart out. It is indeed possible to do all these things in one day without stepping foot in a car. I call these kind of days, a “Great Chicago Day.” When it all comes together, it’s like a pub crawl, a dinner party, restaurant week, opening day, an architectural tour, and the last day of school all rolled into one.
When venturing out for a Great Chicago Day, the point is to bounce around rather than linger at any one spot too long. Maybe plan a few stops, but keep an open mind for those unexpected discoveries and jump at opportunity when it arises. You can do the day solo, but its best enjoyed with a sidekick. If you have a larger group, it limits your ability to get seated without a reservation or squeeze into that lost slot at the bar.
Forget the car. You don’t want to deal with the parking or the traffic. You don’t even want to take your own bike. You don’t want to be tethered down and it’s more fun to mix up your mode of transport around the city throughout the day. Start off on foot and rely on taxis, public transport, Divvy, Lime, etc. The city’s flatness is a benefit here as much can be explored on foot, and every neighborhood is serviced by public transportation. If done right, your Great Chicago Day will involve you getting on the Chicago River Water Taxi at some point.
Without question, when it comes to food and drink, from the finest dining to the dingiest of dives, Chicago will go toe-to-toe with any city on earth. And to really enjoy all that the city has to offer, you should be willing to venture to both ends of that spectrum. A Chicago Dog, Italian Beef, or Quesabirria can be every bit as transcendant as the ribeye at Bavette’s or the tasting menu at Alinea. Much like New York or London, you can find a restaurant for just about every country on earth, but in Chicago these things tend to come in bunches. From the Vietnamese restaurants, markets and cafes of Uptown/Argyle to the German bars and fests of Lincoln Square with Chinatown, Little Italy and Ukranian Village in between—just to name a few—you can easily spend a day hopping continents all within the city limits. Rather than being defined by socioeconomics, the character of many neighborhoods exudes the flavor and cultural vibes of its early inhabitants, and these often shift in a matter of just a few blocks.
Chicago might not be as musically-minded as Nashville or as art and fashion-heavy as New York, but you better believe there’s world class institutions for all of the above. From clubs to galleries to street fests, you will find something to suit your taste.
Unlike many other metro areas, all of the major sports stadiums are within the city limits—if not tucked into neighborhoods themselves—making it easy to work them into an itinerary. If you aren’t a fan of any of the Chicago teams, the city is a magnet for much of the Midwest, so no matter how bad the Cubs, Sox, Bears, Bulls, Hawks, or even the Fire are playing, there is always a team to cheer on somewhere. On my street alone, I know a Bears fan, a Lions fan, a Packers fan, a Steelers fan, a Bengals fan, a Browns fan, and a Bills fan. There’s even a Chicago bar dedicated to Las Vegas Raiders fans for chrissakes.
The climate forces the scheduling of the majority of the festivals to be condensed into just a few months—not to mention the long-standing pastime of neighborhood groups creating their own block parties—which means its nearly impossible to avoid simply stumbling upon some sort of public party.
A Great Chicago Day starts early and ends late. Breakfast lunch and dinner are to be enjoyed out of home. If you aren’t sure where to start, consider incorporating a few of the following into your adventure:
ACTIVITY
Do a physical activity. Hit some balls at the Diversey Driving Range. Call that friend with a sailboat. Bike along the 606. Kayak the Chicago River.
CULTURAL INSTITUTION
Visit a cultural institution. The point here is to just skim the surface of one of these beauties. Do a leisurely stroll through the Lincoln Park Zoo, peruse a few rooms of the MCA, catch a few innings at Wrigley, or just admire the skyline from the Planetarium.
COFFEE
Metric, Eataly, Le Colombe, Ritual, 3 Arts Club Cafe, to name a few.
INTERNATIONAL
Eat/drink something “international.” Moroccan mint tea from Shokran. A Vietnamese banh mi from Nhu Lan. Filipino Sisig from Boonie’s.
HIGH
Eat/Drink something fancy. Dine at the bar at Bavette’s. Try the crudo at Nobu. Enjoy a martini at RL.
LOW
Eat/Drink something low brow. Chicago really surprises when you discover the wings at Budacki’s, the birria tacos at Quesabirria Jalisco, or the Depression Dog from Gene & Jude’s.
SWEET
Eat/Drink something sweet. A Paris Brest from Southern France Patisserie. A Beard Papa cream puff. Oreo Drop Cake from Te Amo. A bag of goodies from Amy’s Candy Bar.
CLASSIC
Visit a “Chicago Classic.” Pequod’s. Berghoff. Manny’s. Rainbow Cone. Twin Anchors. Second City. Green Mill. These are the places you take for granted, but are always worth a visit.
FRIEND
Work some friends into the mix. Bonus points if you meet up with someone you haven’t seen in a while.
NEW
Try something you have never done before. Get a hot towel shave. Try a platza at Bath House. Go see a drag show, magic show, improv show, or a traditional Irish session.
OUTDOORS
Hang out on a patio and/or rooftop. Take in mind-blowing lake and architecture views from Cindy’s. Grab a beer and sausage on the roof at Gene’s. Or simply watch part of the game on the patio at Roscoe Village Pub or the roof at Reggie’s.
LATE NIGHT
Work in a night cap and/or late night bite. Fire Chicken from Dancen. A burrito from Allende. One for the road from Snickers. Yes, Snickers.
Let me create a Great Chicago Day Itinerary for you…
