170+ Tips for Living in Chicago

Things I’ve Learned in 10 Years of Living in the Windy City

Feeling all nostalgic, I came up with what supposed to be a short list of things I’ve learned living in Chicago — which evolved into about 170 things highlighting food, lifestyle, hacks for living in the city, navigating tourist traps, and everything in between.

Enjoy.

Things I’ve Learned Living in Chicago

• When you say you live in Chicago, mean it. If you live in the city, you live in Chicago. If you live in the suburbs, you do not.
• Real Chicagoans don’t call Chicago Chi-Town or any other derivatives of “Chi.”
• Learn how “the grid” works. It will be invaluable for navigating around the city.
• Every neighborhood has a unique vibe and culture. Explore them and have fun.
• Walk fast. It will serve you well, especially in winter.
• Take advantage of every opportunity to dine al fresco or drink on patios in the summer.
• Best rooftops: Virgin Hotel, Chicago Athletic Association, London House, The Robey, and J. Parker. Soho House if you have a membership. The Wit is overcrowded and The Godfrey is awful.
• For the best city view, go to the Signature Room Lounge on the 98th floor of the Hancock. You’ll pay $10 for a Diet Coke but have great views and not have to wade through tourists on the Observation Deck. Also, apparently the view from the women’s restroom is amazing, so I’ve been told.
• Bikers are terrible about obeying traffic laws and common sense. If you do drive, watch out for them.
• Remember that Divvy bikes are checked out by the minute. I once saw one parked in a building foyer for days.
• SpotHero will be your friend if you own a car and don’t have parking.
• The Music Box is absolutely charming and is a great place to see films.
• Record Check, Please on your DVR to learn about restaurants in the city. I secretly want to be on that show one day.
• Don’t plan to get anywhere in the city during the Chicago Marathon.
• A membership at The Art Institute is totally worth it. For creative inspiration, their After Dark events, and for a cool place to take out-of-town visitors, it’s money well spent. And, you’re investing in the arts.
• TBOX is the worst thing ever, next to bachelorette parties in Boystown.
• NEVER go to Navy Pier. EVER.
• The Brown Line > Red Line if you need to get from downtown to Belmont.
• Living within walking distance of a good coffee shop, great take-out, and a grocery store is invaluable.
• Don’t judge someone if they live in Streeterville.
• The 3 Arts Club at Restoration Hardware is the best place to do day drinking without feeling bad about it.
• The Architectural Boat Tours are really, really cool. I didn’t go to one for 8 years and learned so much about Chicago history and architecture. It’s always a crowd-pleaser, just make sure you don’t go when it’s blazing hot outside. And wear sunscreen.
• Get to know the bartender at your local bar and be nice to your neighborhood baristas.
• Purchase reusable bags for your grocery shopping and use Instacart when you need La Croix. Make someone else carry that home for you, as long as you tip well.
• Always have your packages delivered to work or Amazon/UPS lockers. That’s the only way to guarantee they won’t be stolen or held in an abyss for days on end.
• GrubHub is your friend for food delivery.
• Postmates will go to Taco Bell for you so you don’t have to feel shame.
• If you’re going out with a large group, for the love of all that is sacred, just have one or two people pay and pay them using venmo, Chase QuickPay, or Cash.
• It really does make sense to have a banking account with Chase.
• Mariano’s will grill your meat for you if you don’t own a grill or if you don’t want to stand outside in winter.
• North Avenue Beach is like spring break every day in the summer. Avoid it and go for the smaller, neighborhood beaches.
• When the temps first hit 50 degrees in winter, it’s completely normal and acceptable to wear shorts and flip flops.
• Garden levels are never a good idea, no matter how cozy they may seem.
• The ORK posters of the neighborhood map were fun and cool about 10 years ago. You can do better when it comes home/office decor.
• Every Chicagoan needs to know what the five stars in the Chicago Flag mean.
• NEVER order a chocolate shake at The Weiner’s Circle.
• The greatest nights I’ve ever experienced in Chicago were Obama’s election at Grant Park in 2008 and the night the Cubs won the World Series in 2016.
• Go and see the river dyed green once, but that’s all. Plan to stay indoors on St. Patrick’s Day.
• If you live near the lake, you’ll think we’re being invaded during rehearsals for the Air and Water Show. But don’t worry, everything will be OK.
• Broadway in Chicago season passes are a must if you want to see every Broadway show that comes through.
• If people say a neighborhood is “up and coming,” they are right.
• Anything north of Bryn Mawr is Wisconsin.
• ALWAYS take the Metra to Ravinia, but be sure to leave the show before it’s over, otherwise you’ll be crammed in train with drunks.
• NEVER pay admission to neighborhood fests no matter how persistent people may be about a donation. Tell people you live there and you’re just trying to walk home.
• You think you want to go to the Taste of Chicago, but after one minute after arriving you’ll realize it’s a terrible decision.
• Do people a solid and buy a copy of StreetWise every once in awhile. I always get one each week from my buddy outside of the Starbucks at Roscoe & Southport.
• Restaurants and bars come and go all the time and at some point, you’re bound to be heartbroken over ones that close. (For me: Rose Angelis and Trenchermen. Trench isn’t the same.)
• Follow the traffic pattern on the lakefront paths. If you don’t you’ll know it.
• The illuminated walkway in the United terminal at O’Hare will never lose its charm.
• If you plan to use UberX, plan to know specific directions of how to get where you’re trying to go because the drivers never know.
• Speaking of Uber, you should always cab home if you’re out past midnight. Be safe! Most muggings happen after bars close, so just play it safe and take a cab.
• Don’t be alarmed if you see people riding naked on bikes. It happens once a year.
• ZooLights is a winter wonderland. Go at least once with a group of friends during the holidays. Take a flask to spice up your hot chocolate.
• Places real Chicagoans will never go: Hard Rock Cafe, The Cheesecake Factory, Rainforest Cafe, and the Rock and Roll McDonald’s.
• Places real Chicagoans go: Al’s Italian Beef, Portillo’s, Lou Malnati’s, and Big Star.
• Au Cheval really does have the best burger in town. Just make sure you get it with bacon and egg. And be sure to have a pickleback.
• Lollapalooza is fun but only if you like crowds.
• Even if you don’t like basketball, Bulls games a very entertaining.
• Attend at least 1 Cubs game per year and eat a polish sausage and drink Old Style.
• Go to a Bears game early in the season before the temperatures plummet.
• Invest in a pair of good boots and a warm coat.
• You will learn to loathe salt in the winter.
• If you’re flying out of O’Hare, always give yourself time to go to Frontera.
• If you’re flying out of Midway, eat before you get to the airport.
• Never ask for ketchup on a Chicago dog or you’ll risk public shaming.
• The Gay Pride Parade is fun, but Market Days is the best LGBTQ+ event in the city each year. PrideFest is, well… meh.
• Lincoln Hall is one of the best venues for concerts that’s not overwhelming.
• Purchasing tickets for any event at Soldier Field is a gamble when it comes to weather.
• If you want to see Hamilton, sit in orchestra before row P (the dress circle ceiling gets in the way further back); sit in dress circle before row D (again, low ceilings); mezzanine before row F; and in the balcony only if you want to watch from the rafters.
• Learn how to ride the “El” — I fell one of the first times I rode it when the train came to a screeching halt.
• The Kriskindl Market is worth the hassle. Make sure you drink out of a boot.
• If you MUST take family or out of town guests out to eat anywhere near Michigan Avenue, Foodlife will be a real crowd-pleaser. There’s something for everyone.
• Do whatever you can to get tickets to Andrew Bird’s concert at Fourth Presbyterian Church around Christmastime.
• Chicago has amazing breweries. Explore them and drink local.
• Chicago also has amazing coffee. I picked where I live based on its proximity to my favorite, Intelligentsia.
• As much as you don’t want to admit it, seeing your reflection in the Bean is always fun.
• Maggie Daley Park will give you anxiety if you have children or have nieces and nephews in town.
• Chicago Fire Soccer games are a blast.
• Always Uber to concerts or events at the United Center but be prepared to walk a few blocks to catch a ride home after.
• If you’re attending an event at Soldier Field, have your cab drop you off at The Field Museum.
• Foursided is the best place to get random gifts, cards, and candles.
• Even with the best intentions, you will always eat the entire bag of Garrett’s “Chicago Mix” in one setting.
• Malort is terrible. No matter what they tell you.
• Nothing beats Musical Mondays at Sidetrack.
• Bottomless mimosa brunches are the things dreams and terrible hangover are made of.
• Take vodka soda to the beach in a Nalgene.
• Little Goat Cafe lives up to the hype.
• My family’s consistent go-to has been Dublin’s in Viagra Triangle.
• If you can weasel your way into a membership at Soho House, do it. You won’t regret it.
• The West Loop is IT when it comes to food. Just be prepared for what it will do to your wallet. And your waistline.
• If you commute in a car, Eric & Kathy will be your favorite companions on the journey.
• Nothing is as soothing as Alva Lara’s voice on NPR.
• Chicago weather people have the toughest jobs of anyone on the news.
• Tom Skilling is the man.
• Consider yourself lucky if you were ever able to attend a taping of The Oprah Winfrey Show. (I was on her ninth-to-last episode, her last makeover show… and everyone in the audience got a makeover!)
• The Violet Hour also lives up to the hype.
• Get yourself into The Office at the Aviary. And if you can’t, sit on their patio.
• Get a gym membership and participate in group fitness classes. They are a great way to meet people and stay fit. (I’m looking at you, SoulCycle Southport!)
• No one does anything social in winter, most people gain weight and watch Netflix or binge on TV series.
• You’re going to celebrities around Chicago, but just play it cool. (I’ve seen Heath Ledger, Adele, Harry Styles, David Schwimmer, Chris Martin, Sophia Bush, Sting, Sam Smith, Chris Martin, Scottie Pippen and many more.)
• The more unique the restaurant, the more likely your parents won’t like it. Find some trusty places that you can guarantee mom and dad will like.
• Chicago does have amazing BBQ: Q, Fat Willy’s and Smoque.
• If you’re going to do a trip to somewhere warm, plan it for sometime in winter in Chicago. Escapes in the winter are necessary.
• StubHub is your friend for last minute tickets to anything.
• If you sell anything on Craigslist, meet in a public place and take someone else with you.
• Rent from individual owners, not large management companies.
• The best Indian food you’ll ever eat is anywhere on Devon St.
• Go for Korean BBQ in Korea Town. Just be prepared to smell like charcoal fire the rest of the night.
• Bubble tea at Joy Yee in Chinatown.
• Tacos anywhere in Pilsen.
• The flaming cheese in Greektown.
• Go to HopLeaf for the beer and stay for the mussels.
• The langos at Bohemian House is the stuff dreams are made of.
• The kale salad at RPM (steak or Italian) will make you want to cry it’s so good.
• La Scarloa is a real Italian experience.
• Ann Sather’s cinnamon roll is life-changing.
• Try the frushi at Orange with a Peel in Roscoe Village.
• Lettuce Entertain You Restaurants will never disappoint.
• The spicy potatoes and bacon wrapped dates at Cafe Ba Ba Reeba will give you life.
• The fried chicken at Parson’s… on the patio… with Negroni slushies.
• The best place to get unique gifts and decor is the Renegade Arts Festival. But get there early before the good stuff is gone.
• Pray that you get to experience something like Snowpocolypse at least once. (And if a big storm like that is headed to Chicago, get food and alcohol and invite all of your friends over for a slumber party.)
• Support Misercordia and buy Jelly Bellies from them at stoplights in the spring.
• If you see people with clipboards on street corners, quickly get into an imaginary conversation on your phone.
• Take a day trip to Oak Park and explore Frank Lloyd Wright’s architecture.
• Try a bone marrow shooter at Bavette’s. It’s life-changing.
• Don’t be basic. Don’t go out in River North.
• Eat out every night of Chicago Restaurant Week.
• Critical Mass is freaking annoying when you’re trying to get somewhere, although I have heard it is fun.
• It only takes 2 martini’s at Marty’s in Andersonville to get you feeling good.
• There is a lady that solicits donations for some kind of charity run to help her sister who needs an operation. She’ll show you a binder full of doctor’s reports and notes and a list of people who have donate to help her. She’s been pulling this racket for years. Don’t buy her story but do offer to buy her some food.
• Watch the fireworks during the summer at least once.
• On panhandlers, give them gift cards or offer to buy them food. Don’t give them cash.
• The WORST times to go grocery shopping anywhere are on a Sunday afternoon or Monday night.
• Do all you can to have in-unit laundry.
• Living near the El isn’t so bad. In time, the train sounds like the ocean and is comforting at night.
• Real Chicagoans don’t live downtown unless they are really rich.
• There are some awesome cultural and history museums. Take the time to check them out. (My favorite is the National Museum of Mexican Art.)
• Plan your vacation to somewhere warm in late February/early March. That’s when you’ll really need it.
• Owning a car is a luxury and isn’t necessary. If you do own one, budget at least $200 a year for parking tickets.
• If you’re Christian and single, Park Community Church and Soul City Church are the places to go to meet people.
• If you’re desperate to find parking and see someone struggling to parallel park, ride up close behind them and stress them out. 9 times out of 10 they’ll abort their mission and you can take their spot.
• Owning a dog entitles you to the privilege of going to one of Chicago’s many dog parks. Take advantage of them.
• If you must have a stroller in the city, get one that’s deep vs wide. Double-wide strollers are the worst.
• Find your community, find your people. They could be in a church, a MeetUp group, a gym class, or somewhere else that’s tribal.
• Maxwell Street with give you a polish that will CHANGE YOUR LIFE.
• Concerts in the Park are magical, unless news choppers are hovering overhead.
• Always go to Twitter if you hear a commotion or disturbance of any kind.
• DNAChicago is one the best resources for neighborhood news. Subscribe to your neighborhood’s edition to stay in the know.
• The 606 is Chicago’s version of New York’s High Line. It’s not the same, but it’s fun.
• People live in Chicago for 3 reasons: June, July and August.
• Always have an umbrella in your backpack.
• Visit the Chicago History Museum to learn about Chicago’s history.
• The Second City is a blast for a fun evening with good laughs and has been the launch pad for many SNL alums.
• Nothing is more comforting than the orange glow of the city’s grid when you’re coming in for a landing at O’Hare or Midway.
• Find a local wine store and join their wine club. wineHouse is my favorite neighborhood gem.
• If you plan to move, do it in spring and hire movers.
• Lake affect snow and thunder snow are real things.
• The colors on the spires of the Sears Tower and Hancock Tower mean something.
• Lake Michigan’s water temperature is above freezing for about a week in the entire year.
• Never believe Yelp reviews, always trust your friend’s and co-worker’s recommendations.
• If you’re Republican, sorry, your vote won’t count.
• Always support your local, independent anything. Chains are the devil.
• Free days at any museum are the WORST days to go.
• There’s a lot of injustice in our city and we all need to do our part to make things right.
• Support local charities with your time and your money.
• Volunteer for causes that matter to you.
• Take time to look people in the eyes and smile.
• Be kind.
• If you dream big and work hard, you can do anything you set your heart to do.
• Chicago is a drinking town with a sports problem.
• Chicagoans are passionate and loyal
• Chicago is a city with broad shoulders and big hearts.
• Chicago isn’t the Second City, it’s #1 to me!

Things I have yet to do in Chicago

Ten years has been a long time to do a lot things in Chicago but there are still a few more things on my to do list:

• The SkyDeck at Willis Tower
• Lollapalooza (but I’ll only do it if I am VIP and have a golf cart)
• The “Tilt” at the Hancock
• A segway tour
• Find a friend who has a boat
• Eat at Carnivale (I haven’t gone out of principle)
• Eat at alinea (a man can dream!)
• Attend a Blackhawks Game
• See a show at the Steppenwolf Theatre
• Drive to the burbs to see the Home Alone house
• Run the Chicago Marathon (one day, maybe)
• Attend a taping of Windy City Live
• Be an extra in a movie or a TV show.