From the booze to the blues, city life in Chicago has its perks, but to live here like a boss, it helps to know some shortcuts and tricks. After moving to Chicago, your first year is full of learning and experiencing. You know: sitting in mysteriously wet CTA seats, arguing about ketchup, watching umbrellas crumple in the wind. After a few more years, you're able to tick off most Chicago rites of passage. Then it's time to get 50 Shades of Grey on this town. Become a master of Chicago with these tips accumulated over decades of living here. Sorry, we still can't do anything about the cold.
Getting around
1) Want to get north-south quickly, or vice versa? Take Larrabee Street. Fastest way east and west? Grand Ave.
Grand Avenue is a wide-open, low-traffic diagonal line from 400 N Western to Narragansset and Fullerton, making it a superhighway for Humboldt Park and southwestern Logan Square residents. Heading vertically on the map? The lesser-used Larrabee is sandwiched between the more trafficked Halsted and Clark Streets.
2) Take the Water Taxi to Chinatown.
Riding a boat up to Ping Tom Park is a quick and lovely way to Chinatown, especially if you're coming in to the city via Metra.
3) Use the Pedway system.
When slush blankets the sidewalks, temperatures begin to drop or rain starts to fall, the Pedway is the route of choice for savvy downtown pedestrians. The underground system of tunnels stretches across the city, allowing you to move between CTA stations, City Hall, Macy's, the Aon Center and more—all without going outdoors.
4) Avoid crowds at the next El stop. Use Argyle after an Aragon or Riv show, Sheridan for the Cubs or the 35-Bronzeville-IIT Green Line for the Sox.
We hate herding onto the tiny Lawrence platform after a big Uptown concert. It pays to walk a few extra blocks. Head north after a gig, and after a Cubs game, too. Not that the Sox crowds are too big, but if so, trot just over the highway to the Green.
5) Download an app to avoid Uber surge rates.
To avoid those ridiculous quintupled Uber fares, download the app SurgeProtector to see the areas where the ride-sharing service is not charging surge rates.
6) Share a Ventra card.
If you live with a sig o, only one of you should get the monthly unlimited-rides pass, while the other gets the pay-as-you-go option. Assuming you two spend some time apart (and you really should—it's healthy), whoever is using the CTA to go out on the town takes the unlimited pass to make sure you're getting your money's worth.
7) Download the vital Transit app.
Designed in Montreal, this public-transportation tracker is a life changer. It works in many cities around the globe, but close to home in Chicago Transit reliably follows all buses and trains near you, as well as taxis and Divvy bikes. Put the CTA at your mercy.
8) Need parking for the Mag Mile or MCA? Use Spothero.
Instead of circling endlessly on the hunt for parking, use Spothero, both an app and website, which rents spaces daily. We easily found spaces in the 222 E Huron garage, and other nearby nooks you might not think of.
Eating and drinking
9) Follow restaurants on Twitter for deals, less wait.
We follow lots of restaurants on Twitter and Instagram, and as a result find out about some pretty cool happenings. For instance, if you follow Fat Rice, then you’d have known it was opening two extra days the last week of December and would have gotten a table much easier. The Twitter handle also alerts followers when there’s no wait. Restaurants also tweet about specials a lot, which is how we learned about—and ate—Smalls Smoke Shack’s escabeche-topped cheese fries.
10) Go to the other Doughnut Vault, the other Kuma's.
Waits too long at Doughnut Vault or Kuma’s Corner? Good news: There are second locations of each (Kuma’s is at 666 West Diversey Parkway and Doughnut Vault is at 111 North Canal Street), and neither gets even close to as crowded as the original location.
11) Lunch in the Loop for less at a hidden cafeteria.
The word "cafeteria" may bring back memories of mystery meat and boiled vegetables, but the Loop's selection of buffet-style dining locales actually offer tasty, healthy and cheap alternatives to tired burrito and sandwich shops. We're fans of the gigantic salad bar in the Vault Cafeteria (135 S LaSalle St ) and the food court feel of Urban Market (10 S Dearborn St).
12) Find better food at Cubs, White Sox games.
There are very solid food options at both Wrigley and the Cell—if you know where to look. At Wrigley, head to the small outside upper deck, where you can get freshly cooked Polish sausages with grilled onions, unlike the pre-wrapped hot dogs you’ll find inside. At the Cell, zero in on the elotes, a really good version of the Mexican corn dish, or the bacon on a stick, which is nicely crisp and served on a stick, so you won’t get your hands greasy.
13) Go to brunch at 1:30pm or when the doors open.
It seems that everyone emerges from their beds on Sunday morning at the exact same time. But we’ve found that brunch waits that are interminable at 11am are nonexistent at 10am or 1:30pm. Go right at open or the end of service, and you’ll be able to get a Bloody Mary much more quickly.
14) Double down in Bridgeport with Maria's and Pleasant House.
The absolute best pairing in the city is Pleasant House Bakery and Maria’s Packaged Goods and Community Bar in Bridgeport. Head over to Pleasant House, order a British pie (or the killer rotating burger every Tuesday), then go to Maria’s and wait for your delivery over a beer or cocktail.
15) Use the take-out window at Big Star.
In the summer, skip the wait for a patio table at Big Star and just head to the take-out window—there’s no booze, but you’ll get your tacos quickly and then can find a more spacious patio to hang out on. (Hint: It’s Parson’s Chicken & Fish).
16) Avoid crowds, and often upgrade your food, with these no-wait replacements down the block: Maude's for Au Cheval, Authentaco for Big Star, Slurping Turtle for Ramen-San.
On three occasions in the past year, we’ve been told the wait for Au Cheval was at least two hours. So we left and immediately snagged a table at Maude’s, from the same restaurant group, Hogsalt. Maude’s may not have burgers, but it has exceptional steak tartare. Want ramen? Skip the wait at Ramen-San and go to Slurping Turtle (which also has much better ramen, so win-win). The wait for Big Star can take ages, so in those instances, we’ll be heading to Takito Kitchen or Authentaco.
17) Visit the "Littler" Italy at Oakley and 24th instead of Taylor Street.
Our city is loaded with great Italian restaurants, but sadly the options in Little Italy are disappointing. For better and less touristy "red sauce" joints, seek the small pocket of Italian culture at Oakley and 24th in the Heart of Chicago, tucked in the corner of the Lower West Side.
18) Get a free dessert at Flat Top Grill with this recipe.
There's a reason they put these joints near colleges—it's a cheap way to eat a ton of food. As broke and hungry newcomers to the city, we had no interest in splurging an extra six bucks for a dessert. Here is hack for free sweets that works at any create-your-own-stir-fry eatery. Take packets of Sugar in the Raw from the table, dump it in a bowl with pineapple. Add in some peanuts and a dash of cilantro. The fruit comes back from the grill hot and caramelized.
City living
19) Be like George Costanza and know these first class downtown public restrooms.
When nature calls while you're walking the Loop and you don't feel like paying for a cup of coffee in exchange for Starbucks bathroom privileges, you have a few options. There's a clean public restroom in the basement of Block 37, some easily accessible and luxurious toilets in the Hotel Allegro lobby (near the Theater District) and plenty of stalls situated below the Pritzker Pavilion.
20) Bring skates to Maggie Daley Park.
The city's new ice skating ribbon has more in common with a Mario Kart track than a frozen pond, allowing you to zip around a slick circuit in the shadow of the skyline. On weekends, you'll be greeted by a long line of people waiting to rent skates but you can usually jump directly onto the rink if you BYO skates.
21) Forget the coffee shop and work on the ninth floor of Harold Washington Library.
Sometimes the Winter Garden (pictured above, lower right) is rented out for private events or hosts author readings, but when there’s nothing happening there, the huge, gorgeous atrium is one of our favorite places to work. With a glass dome ceiling, marble floors, greenery and wifi, it’s a beautiful space to spend an afternoon.
22) Take tourists to free comedy shows.
"Harold" shows feature a pair of iO improv teams building a show out of an audience suggestion and run every night, but on Wednesdays you can catch these hilarious performances for free and get a taste of some of iO's trademark long-form improv. And there's no better showcase for the on-the-fly skills of Second City comedians than the free improv shows, which follow the last performance of every night but Friday.
23) If you're a movie buff, use Moviepass.com.
For just $30 a month, this frequent watcher's card allows users to see a unique film every 24 hours (no 3D or IMAX). Most Chicago theaters participate, including the AMC and Regal chains, as well as indie spots like Music Box, Facets and the Gene Siskel Film Center. With constantly rising ticket prices, start saving money after just three flicks per month, leaving you with extra cash for the concession stand.
24) Score free museum passes at the library.
Want to take a gratis trip to a museum without waiting for the next free admission day? Take a trip to your local library and check out a pass to the Field Museum, Art Institute, Adler Planetarium and more. Each pass gives a family of four (two children and up to two adults) free general admission to a museum during regular hours.
25) Swim in a less popular pool.
The Holstein Park pool in Bucktown is a place to be seen—which is why it's jammed with sunning bodies. For less crowded waters, try Hamlin in Roscoe or head south to swimming pools in tucked away Smith Park or spacious Douglas Park. Looking to do laps? Indoor Fosco Park is a good bet.
26) Get the Dark Sky app and be your own Tom Skilling.
In Chicago, weather can change wildly by the hour. This app can predict rainfall to the precise minute. It kept our butts dry during the great derechos of the last two summers. It's basically like having Tom Skilling and Thor whispering to your phone.
27) Always use the north gate at Lollapalooza.
With a tangled mass of fencing and teenagers, trying to get into Grant Park from Michigan Ave can make you feel like livestock at the state fair. Reject the allure of the big, pretty fountain and never, ever enter Lolla that way. Stroll in the north end by the Modern Wing and you're steps away from the main north stage.
Note: At the request of readers, we have changed 8) to a general parking app, which can grant you access to parking in the aforementioned public lot and many other lots.