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The Most Helpful Guide for New Chicago Renters

Are you a new Chicago renter? The Windy City is chock-full of opportunities for working, playing, eating and drinking. And while the magnitude of it all can seem daunting at first, we’re here to help.

Read on for our tips on navigating the best Chicago has to offer.  

Seasons and Landmarks

As you settle into the city, prepare yourself for biting winds off the lake in the winter and the scalding stickiness in the summer. Chicago weather isn’t a challenge for the faint of heart, but those who make it through the first winter will find that one of the best things about the city is its ever-changing seasons. It’s hard not to fall in love with the way Lake Michigan looks when it’s frozen, or the smell of leaves falling as they waft in the breeze.

The Windy City is truly a grabbag of different climates, so make sure when you move in you pick up both a snug scarf and a super-sized bottle of sunscreen.   

You’ll also need to know some red flags to avoid, dead giveaways to locals that you hail from out of town. For example, you may see or hear about Willis Towers, but to locals it’ll always be  Sears Tower, located on South Wacker Drive. Calling the Bean the “Cloud Gate” borders on sacrilegious. To bone up on your Chicago history, stop by the Chicago History Museum, on the southern edge of Lincoln Park, on the corner of Clark Street and North Avenue.

And finally, locals never put  ketchup on that hot dog (but instead use hot peppers, celery salt and relish so green you’ll wonder if it’s fake – more on that in a moment), and your pizza of choice should  now be anything deep dish.

Know your Chicago neighborhoods and suburbs: Faux city-dwellers will say they’re from Chicago when they live in the suburbs, and it’s now your job to call them out on that transgression.


No matter your preferred method of  getting around, you can find plenty of ways to traverse Chicago’s avenues with the city’s robust transportation system.

If you’re an avid biker, take advantage of the city’s network of connecting bike lanes, which are anchored by the 18-mile lakefront path that stretches from Sheridan Road on the city’s North Side to 71st Street on the South Side. It’s a quick way to reach your destination while also getting in your exercise for the day! Even if you don’t own a bike, you can take advantage of the Divvy bike-sharing program, which allows you to rent one for a small fee and drop it off at one of many convenient locations throughout the city.

If biking isn’t your thing, the Chicago Transit Authority (or ‘CTA’ for short) features a grid of train lines and bus routes, and if you use them in tandem, you can get to pretty much anywhere in the city for just $2.50 and applicable transfer fees. Use the Ventra app to load your train card, check arrival times and get notifications about expiring passes. You can also buy Metra train tickets on the go with the app as you ride out to Chicagoland suburbs, or as far north as Kenosha, Wisconsin. The Amtrak train lines are your gateway to the perfect weekend getaway, as the Union Station hub has pathways to stations all across the country.     


Chicago is a diverse city, comprised of people who hail from all across the world and bring culture-inspired dishes to the area landscape. Fortunately for you, that means there are a staggering number of top-notch dining options, so adventurous foodies will never get bored. As mentioned above, a good starting point for the newly initiated is a deep-dish pizza. Giordano’s, Lou Malnati’s, Gino’s East, and more, there’s a new place to try almost every week of the year. Plan to get to them all in your first year as a Chicago renter.

Other famous dishes from the city include Italian beef sandwiches, which were purportedly invented by Chicago staple Al’s Beef (Portillo’s is a great second choice and more conveniently located all over Chicago), and Chicago-style hot dogs, which feature an all-beef hot dog on a steamed poppy seed bun, topped with yellow mustard, relish, tomato wedges, chopped onions, a pickle spear, hot peppers and celery salt. Invented for the Chicago World’s Fair, it’s an intimidating sandwich at first, but one worth trying at least once, if you’re really going to become a true Chicagoan!

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